Older Hero vs. Younger Villain

"John, you're a Timex watch in a digital age. You're gonna lose."

— Thomas Gabriel to John McClane, Live Free or Die Hard

A principal character who is supposed to be significantly older than most is opposed by a villain who is relatively young and apparently in their physical prime.

The plot often leads to a fight in which the young villain sneers that their victory is inevitable because they're younger than the older hero.

In these kinds of plots, the young villain will typically be introduced as they one-up the old hero as a part of their scheme, because You Can't Thwart Stage One. However, the older hero eventually rises again and soundly defeats the young villain. At or near the end, the old hero proclaims something like "I may be older, but I'm better!" Furthermore, the other principal characters quickly agree that the older hero is still a valuable member of the team.

Usually, what eventually causes the scales to tip back in the hero's favor is that them being older also means that they are wiser and the fact that Youth Is Wasted on the Dumb. Some version of the saying "Youth and enthusiasm will never be a match for age and experience" may appear, leading the hero to realize that while they might not be able to defeat their younger opponent through physical strength alone, they can outsmart the villain, either through superior combat experience if it comes to a direct confrontation, or, if the hero is the more shrewd type, by playing on their opponent's youthful recklessness and impatience to trick them into doing something that becomes their own undoing.

Compare Childish Villain, Mature Hero, wherein the hero and villain are contrasted by the age their attitude is similar to rather than their actual ages, though both tropes can overlap.

Contrast Pick on Someone Your Own Size, Evil Old Folks, and Kid Hero. Can be the result of someone Avenging the Villain. The young villain can also be a Pupil of the Older Hero Until They Turned To Evil. See Antagonistic Offspring for when the Younger Villain is the Older Hero's child and Intergenerational Rivalry.

Examples:

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Anime & Manga

Bleach:
- Yamamoto, who has led the Gotei 13 for a millenium does battle with Aizen, a relatively young Soul Reaper who became a lieutenant about 110 years before the start of the series and a Captain nearly a decade after that.
- Most of the Captains and Visoreds participating in Fake Karakura town battle are older than the aforementioned main antagonist (especially those characters, who fight him directly), who is rather young, but still older than several other heroes.
- Yoruichi fights her former subordinate and student Suì-fēng during the Soul Society arc. Yoruichi is trying to save Rukia from being executed on false charges, while Suì-fēng is trying to stop her.
- Averted with the Wandenreich, and most of the Sternritter, as many of its higher ranked members approach about a thousand years of age, and thus being considerably older than most of the Soul Reapers, with the only exceptions being the members of Zero Squad.
Death Note: According to supplementary material, L Lawliet, the world's greatest detective, is aged 24 and Light Yagami, the Serial Killer L is trying to catch, is aged 17 prior to the Time Skip.
Dragon Ball:
- The original Dragon Ball has Goku fighting against Piccolo Jr. While they are both approximately teenagers at the time of the fight, the latter is only three years old, versus the 18-year old Goku.
- Cell in Dragon Ball Z is chronologically only 4 years old by the time he makes his first appearance and yet, he managed to obtain enough power to curb-stomp the significantly older heroes, even having enough power to destroy the whole solar system.
- While not an outright villain, Dragon Ball Super has Goku and Vegeta both fight against Caulifla & Kale and Cabba respectively, all whom looked to be significantly younger than the Saiyans of Universe 7.
In Final Fantasy VII: Advent Children, Kadaj looks to be in his mid to late-teens whereas Cloud is in his early twenties. In fact, Kadaj (and his brothers) can't be older than two. One of the creators did mention that he wanted Cloud to face someone younger than him.
Fullmetal Alchemist:
- Van Hohenheim, the Big Good of the series, looks middle-aged, but has lived for more than 400 years. The Big Bad, Father, was created from his blood and is younger than him.
- Fu, an elderly retainer to Ling Yao and one of the oldest human characters, faces off against Wrath, also known as King Bradley, a human-based homunculus. Wrath comments that it's impressive how quickly Fu moves despite being even older than Wrath.
Inuyashiki's eponymous hero is 58, and looks even older than that, whereas the Big Bad Shishigami is a teenager.
JoJo's Bizarre Adventure: Stardust Crusaders
- The Older and Wiser Joseph Joestar is the old hero against many of the enemy Stand users, particularly in his fights against the young women Nena and Mariah.
- High-school student Kakyoin Noriaki ends up facing against the baby Mannish Boy, whose Stand lets him trap and kill people in their dreams.
While Monster's Tenma is by no means old, he's got a good 15+ years on Johan, who started exceptionally young.
The old gardener Sul from Kiss Wood defies the authoritarian young dictator Mua in her hellish garden.
Lyrical Nanoha:
- In StrikerS Sound Stage X, the main culprit turns out to be Teana's subordinate Runessa, who is a year younger than she is.
Page vs. his former student Enchu in Muhyo and Roji. Muhyo's quite young himself, although his age is never specified, and he sometimes has to deal with the spirits of those who died in childhood (but depending on when they died, they might technically be older than he is).
My Hero Academia:
- The plot as a whole is an inversion with All For One and Tomura Shigaraki, the main League leaders, being older than the freshman students that are 16-17. The former is so old thanks to a stolen Quirk that he's Shrouded in Myth and the latter is at least in his 20s. This also means that Tomura was still a child before most of the students were born.
- All Might vs. Tomura Shigaraki during the League of Villains raid in UA. The former's age isn't specified, but he's middle-aged, and significantly older than Shigaraki.
- During the battle against the League of Villains at the training camp, Kendo and Tetsutetsu, both first-years in high school, end up facing off against Mustard, who's apparently a middle-schooler.
- The fights between Endeavor and his Arch-Enemy Dabi during both the Paranormal Liberation War and the Final Battle qualify, especially after it's revealed in the former that Dabi is Endeavor's supposedly-dead son Toya.
My-HiME has an arc where the various HiMEs who are at youngest middle school age and at oldest full adults go up against nine-year old Alyssa Searrs.
In Naruto:
- Sasuke, in his tenure as a Villain Protagonist fought against Killer B, as well as the five Kages (with Danzo as the acting Hokage in place of Tsunade), all of whom are clearly older than him (sans Gaara).
- As part of Orochimaru's attempt to crush Konoha at the end of the Chuunin exam, the Third Hokage Hiruzen Sarutobi battles Orochimaru himself. Orochimaru's mind/soul/consciousness is 50-51 at the time, but his body at that time is young, while the Third Hokage is 69. Also, Orochimaru's was said Hokage's student in his days as a Genin.
- Jiraiya's mission to track the leader of Akatsuki ends up pitting him against his former student, Pain. Jiraiya is 54 and Pain is 35, though Nagato is using the body of his deceased friend and former fellow student Yahiko (who died at the age of 15). This is even lampshaded when he comments on the irony of Pain treating him like a child when Pain dismisses his views as childish.
- Also, the fight that led to the release of the Kyubi, and the sacrifice of the Fourth Hokage pitted Minato, the Fourth Hokage himself, who at age 24 and married to Kushina, whom he protects was also older than his last opponent, the teenage Tobi, who is actually his student, Obito, and was declared KIA at age 13.
One Piece:
- The 72-year-old Whitebeard fights against both Marine Admiral Akainu (53) and ex-member of his own crew, Blackbeard (38).
- Iceburg, the 38-year-old mayor of Water 7, ends up being investigated by Lucci, a man 10 years his junior who infiltrates the company and works as his subordinate in order to obtain Pluton's blueprints for the World Government. When Lucci asks if Iceburg doesn't trust the World Government, Iceburg says "I just know human nature... boy."
- Also, Brook's brief fight with Big Mom during the Straw Hats' journey to Whole Cake Island, after Big Mom took him as an exotic creature. While both are elderly, Brook is 90 (and died for the first time at 38-years old) and Big Mom is 68.

Comic Books

In the classic comic, Batman: The Dark Knight Returns, the Dark Knight, who is feeling very insecure about getting older, decides to fight the young and inhumanly strong leader of the Mutants hand to hand. As a result, Bats is badly beaten and barely escapes with the help of a new Robin. After he's recovered, Batman arranges a second fight, but this time, he does it intelligently by handicapping the fighting area, using a mudhole to limit his opponent's movements, and using his superior experience in fighting techniques to overcome the villain's physical superiority. Although they are roughly the same age, Superman's perpetually youthful appearance and infinite energy make him look like this next to the battered, aging Bruce Wayne during their climactic showdown.
In Buffy the Vampire Slayer Season Eight, Buffy takes on the rogue Slayer Simone Doffler. Buffy tells Simone that she's been a Slayer longer and is more experienced, whereas Simone retorts that she's younger than Buffy and thus faster. It's also downplayed, since Buffy's still in her early-to-mid twenties.
In Deathstroke, Slade is targeted by a younger villain, Jannissary, who repeatedly hails him as "old man", but defeats him. Subverted in that Jannissary had been hired for the job, by a man who (accurately) says that Slade is out to kill him; when Slade has Jannissary at his mercy, he explains why. When Slade goes in for the kill, he first returns the money paid to Jannissary and expresses his admiration for Jannissary's principles.
Disney Ducks Comic Universe:
- Although he may not necessarily be a strapping young man himself (depending on whether or not you're going by Don Rosa's canon), Evil Counterpart John D. Rockerduck is the younger villain to Scrooge McDuck's older hero. Not to mention Magica De Spell and several of the Beagle Boys. You'd be hard pressed to find a notable enemy of Scrooge who wasn't significantly younger than him.
- Except his better Evil Counterpart Flintheart Glomgold and The Beagle Boys' grandfather, founder and occasional leader Blackheart Beagle.
- This trope could be considered one of the few things that make Rockerduck different from Glomgold: Whereas Glomgold is basically Scrooge as he would've turned out if he hadn't "made it square", Rockerduck is a more modern businessman who is willing to spend away his fortune if it suits him and is sometimes depicted as being more accepted by society than Scrooge is.
- A collection of classic Rockerduck stories mentioned in the introduction that by what passes for canon in Disney stories, Rockerduck is Scrooge's superior in some markets, like media and entertainment, because Scrooge doesn't "get" the concepts well enough to apply his talent for business to it. The usual solution is to rope in his younger relatives, actually needing their advice and not just their underpaid hard labour.
Green Lantern: In the mid-1990s, Hal Jordan became supervillain Parallax by killing his former friends in the GL Corps, his former mentor Sinestro and absorbing the GL Corps main power source (during the "Emerald Twilight" arc). In the follow-up issue, Ganthet, the Corps' only survivor, chooses Kyle Rainer as Jordan's replacement. At this point however, Hal Jordan was a veteran Green Lantern and had some graying hair on his head, while Kyle Rainer was, in his civilian life, a freelance artist wanting to leave his hometown with his girlfriend Alex. Hal and Kyle eventually cross paths and come to blows regarding the legacy of the Green Lanterns.
Judge Dredd: Judge Dredd's adversary with serial killer PJ Maybe. Joe looks younger than he really is due to futuristic rejuvenation treatments, but he's actually 80. Maybe has been on Judge Dredd's radar since he was a teenager until his final demise three decades later.
Kingdom Come features an entire generation of older heroes doing battle with younger '90s Anti-Hero types. Though in that case it's acknowledged that the older generation is just as flawed as the younger and Both Sides Have a Point.
In the comic book Sin City by Frank Miller and the associated film, the Yellow Bastard ridicules Hartigan that he is "too old to even lift that cannon [he] is carrying." Of course Hartigan wins the day, and then kills himself after saving the girl, because he's so old it's not worth himself staying alive and keeping Nancy, a young woman, a target.
Wonder Woman is usually much older than any of her opponents that aren't old gods like Ares. It's not always readily apparent due to her stopped aging keeping her appearance as that of a young woman.

Fan Works

The Pokémon Reset Bloodlines Elite Four Drake Interlude pits the title character (seventy years old) against Hunter J (age unknown, but presumably in their late twenties to early thirties at most). It's a twofold example, given that they have their Salamence battle against one another to a stalemate, and Drake's is significantly older than J's.

Films — Animated

In Barbie and the Secret Door, seventeen-year-old Alexa must contend with ten-year-old Malucia.
Cars 3 has seven-time Piston Cup racing legend Lightning McQueen compete against rookie Jackson Storm, an arrogant and nasty next-generation racer as he tries to avoid being forced to retire from racing forever.
Despicable Me has a rivalry between the middle-aged Diabolical Mastermind Gru and his young, smarmy rival Vector. In fact a particular theme of the film is that Gru was once the greatest villain of all time, but as time has passed and new younger villains have risen, who are implied to be phazing out the old. Although this example ends up being retroactively subverted, when in the second minion movie it is revealed that they were in fact almost the same age.
The Incredibles has Mr. Incredible, who's had three children during the 15-year Time Skip, set to battle against his young former fan, Syndrome.
Kung Fu Panda has Master Shifu pitted against his adopted son Tai Lung.
The Lion King (1994) has Mufusa and his jealous younger brother Scar.
Sleeping Beauty (1959): The middle-aged heroic fairies Flora, Fauna and Merriweather vs. the younger-looking evil fairy Maleficent.
Inverted in Up. The 78-year old Carl Fredricksen vs. his former idol, the 93-year old Charles Muntz.

Films — Live-Action

Bad Boys for Life has Armando as the biggest physical threat to Mike Lowery. This is highlighted in their first fight which Armando dominates. By this point Mike is approaching his fifties, while Armando is a young man. Armando is in many ways a younger Evil Counterpart to Mike himself. This is because Armando is Mike's son, raised by his mother Isabel, Mike's vengeful ex-lover and cartel boss, to be capable of bringing down his father.
In Batman v Superman: Dawn of Justice, Lex Luthor is a fair bit younger than Bruce Wayne, with Lex being in his early 30s, plus looking younger, whereas Bruce is in his mid-to-late 40s.
The Beekeeper has Jason Statham as Adam Clay in his 50s while Josh Hutcherson as Derek Danforth is in his 20s.
Class of 1984: Protagonist Andrew Norris is a school teacher somewhere in his thirties who is antagonized by a group of teenage delinquents.
In Dragonheart: Bowen, a knight of the Old Code, eventually fought back against his former pupil, Einon, when he became king and showed he was just as vile as his father, if not moreso.
Django Unchained has Dr. King Schultz played by Christoph Waltz with the villain of Calvin Candie played by the much younger Leonardo DiCaprio.
The Expendables has Barney Ross played by Sylvester Stallone with the younger villain James Munroe played by Eric Roberts, Jean Vilain played by Jean-Claude Van Damme and Conrad Stonebanks played by Mel Gibson. Todd Roll played by Randy Couture with the younger villain Dan Pain played by "Stone Cold" Steve Austin. Lee Christmas played by Jason Statham with the younger villain Hector played by Scott Adkins and Suarto Rahmat played by Iko Uwais.
Gladiator has Maximus (Russell Crowe) fighting younger villain Commodus (Joaquin Phoenix).
Another loose definition of "he ro", in Godzilla (2014) we have Godzilla, who is literally millions of years old, vs the MUTOs, who are only a few days old.
The Highwaymen: Hamer and Gault are two aging Texas Rangers who came out of retirement to hunt down Clyde Barrow and Bonnie Parker, a young Outlaw Couple.
Holocaust 2000: Robert (Kirk Douglas) is an industrialist who is nearing retirement. The Antichrist is his own son Angel, a good thirty years younger than him.
The Hunted (2003) is all about Tommy Lee Jones having to take down his former student Benicio del Toro who has gone rogue.
In the Line of Fire: Frank Horrigan is a Secret Service Agent nearing his retirement. Mitch Leary is an ex-CIA assassin a good twenty years his junior.
Has happened a few times through the James Bond film series:
- Being the oldest actor to play Bond, many of Roger Moore's Bond villains were younger that him. The only ones who were older than Moore's Bond are Scaramanga, Stromberg and Kamal Khan.
- During Pierce Brosnan's run, the only villain who was older than him was Elliot Carver in Tomorrow Never Dies. Trevelyan from GoldenEye was roughly the same age, and the Big Bad of The World Is Not Enough was, well, different as far as Bond villains go, with a very different dynamic. In Die Another Day, the Smug Snake Gustav Graves is a younger Shadow Archetype to Bond, what with having his own gadgets, Dark Action Girl, and dangerous exotic lifestyle. His Dragon —about the same age as he is— even has his own Bond car.
- Spectre: While C is not quite a villain to Bond or M, his idea to end the 00-agent program makes him quite antagonistic to them. The age gap is even greater between him and M, who he actually engages in combat with after revealing he's in bed with Ernst Stavro Blofeld. The difference in their ages is also parallel to the new vs. old ideas of running spy agencies they adhere to — C favors 24/7 surveillance, while M questions if an Attack Drone can do the job of human field agents like 007.
For the loosest definition of "he ro", in Jurassic World we have Rexy, the T. rex from the first movie now in her 20's, as the older (anti-)hero vs the I. rex's younger villain in the climax.
The Karate Kid has Daniel LaRusso played by Ralph Macchio with the younger villain Johnny Lawrence played by William Zabka. Zabka is four years younger than Macchio but in the film one year younger.
Lethal Weapon:
- Lethal Weapon 3: Murtaugh has to blow away his son Nick's friend, Daryl, in a drug bust after Daryl shoots at him. Murtaugh doesn't take it very well.
- Lethal Weapon 4: Riggs and Murtaugh, who are both reaching retirement, face off against Chinese martial artist and crime lord Wah Sing Ku who is the youngest of the main antagonists.
In Live Free or Die Hard, we have John McClane, the world-weary old-school cop vs Thomas Gabriel, the younger high-tech computer hacker.
Logan: Logan himself looks to be in his fifties but is actually 197 years old and is beginning to suffer the effects of old age due to his Healing Factor starting to fail. The villains are the relatively youthful Donald Pierce (played by Boyd Holbrook, who was born in 1981), and the middle-aged Zander Rice (played by Richard E. Grant, who was born in 1957). Taken to the extreme with X-24, who isn't even a month old and deliberately resembles Logan in his prime.
Marvel Cinematic Universe:
- Ant-Man and the Wasp has Paul Rudd (then 49) and Evangeline Lilly (then 38) as the titular Ant-Man and Wasp, respectively, fighting against Hannah John-Kamen (then 27) as the main antagonist Ghost.
- Black Panther has Erik Stevens against T'Challa and Zuri. Killmonger is implied to be younger than T'Challa, and he's perfectly willing to kill his cousin. He does kill Zuri when given the opportunity.
- Captain America: Civil War has some of the Avengers including Tony Stark, Steve Rogers, Clint Barton, and James Rhodes against Baron Zelmo.
- Spider-Man: Far From Home has Talos, who is more than 100 years old and posing as Nick Fury assisting Spider-Man against Mysterio.
Morgan Freeman plays retired prize-fighter Eddie Dupris in Million Dollar Baby, and for most of the movie he is a kind, soft spoken old man. That is, until one of the younger boxers, Shawrelle, started beating on Danger, a young man with a few mental issues who was basically the laughingstock of the gym. He steps into the ring, reassures Danger that everything is going to be alright, and borrows one of his gloves. Shawrelle mocks him, saying: "Now I get to fight a retard, and an old man! Somebody better call ESPN 'cause you can't write this shit!" Dupris punches him right in the face. Suddenly realizing that he's serious, Shawrelle tries to retaliate, but Dupris' years of experience allow him to easily block, and then he hits him again, with his bare fist, knocking him unconscious. Moral of the story: never assume that just because a man has a soothing voice, he can't kick your ass. Because he so can.
New Police Story is a Darker and Edgier reboot of the Police Story franchise, starring Jackie Chan, pushing 50, as a disgraced police captain who lost 9 of his best men to a bunch of young hooligans (their leader being the eldest, played by a then-29 Daniel Wu) and must prevent another police massacre they're about to carry out.
Paul Blart: Mall Cop. After being caught by the Big Bad of the criminals taking over the mall, Paul admits that he was younger, stronger and smarter than he was. And that literally he was the man with the gun.
Prime Cut has The Irish Mob's oldest hitman Nick Devlin being sent out to collect a debt from middle aged slaughterhouse owner Mary Ann, who has committed so many atrocities ranging from secretly selling human flesh to Human Trafficking to the extent that Devlin, for all his own faults, might as well be a saint in comparison.
In Rambo IV and Rambo: Last Blood, the aging Rambo fights against younger-looking main villains.
In Rocky, going by age none of Sylvester Stallone's character's opponents are older than him, the closest being Carl Weathers, who played Apollo Creed, being two years younger then him.
- The first serious contender to face him in Rocky III is the newcomer and rapidly climbing Clubber Lang. The intro montage contrasts his lone ascension in the ranks with Rocky's comfortable championship lifestyle and family.
- Rocky V has the new champion Tommy Gunn. He actually was Rocky's protigee until the relationship soured, now they will have a brawl in the streets.
- The entire plot of Rocky Balboa leads up to Rocky's comeback match against the undefeated 29-year-old champ, Mason "The Line" Dixon, at a point when Rocky himself is just shy of 60.
In She Wore a Yellow Ribbon, you have ageing Nathan Brittles — about to be retired from the army — up against young chief Red Shirt, while bonding with his contemporary, chief Pony That Walks.
In the second half of Soldier, Kurt Russel manages to defeat a force of younger genetically engineered super soldiers thanks to his decades of combat experience.
Star Trek: Nemesis. Old Picard versus young evil crazy dying Picard-clone.
Star Wars:
- In The Phantom Menace, Qui-Gon Jinn and Obi-Wan go up against Darth Maul. The former is 26 years older and the latter is 3 years older.
- In Attack of the Clones, Yoda is forced to fight his former student Count Dooku. Dooku is eighty years old, but Yoda is nine hundred.
- In Revenge of the Sith, Yoda has a lightsaber duel with Darth Sidious. Sidious is 65 and Yoda is nine hundred.
- The Sequel Trilogy has Kylo Ren, Han Solo and Leia's Antagonistic Offspring and Luke's Evil Nephew.
- Similarly, Anakin Skywalker and Obi-Wan Kenobi dealt with this a couple of times after Anakin's fall, with Obi-Wan being Anakin's senior and ex-mentor now having to stop his corrupted student.
In The Score, Nick Wells is a veteran Gentleman Thief that has survived long enough to know when caution is needed (even if means walking away from a heist completely because he cannot fully trust the intel or the people he's working with) while Jack Teller is a Young Gun that is so determined to make a name for himself as a master thief that he jumps the gun (and literally uses guns, which is a big no-no for Nick) and nearly ruins the heist out of believing that there's No Honor Among Thieves and he would get a smaller cut and no recognition.
Targets: Our hero is an elderly horror actor making plans for his retirement. Our villain is a young and active Vietnam veteran.
In The 13th Warrior, an old warrior who'd befriended the protagonist gets challenged by a much younger and larger opponent. He proceeds to prove that skill matters more than size or age in hand-to-hand combat.
TRON: Legacy: CLU has this dynamic with his creator Flynn. Besides their temporal ages, it's exaggerated by the fact CLU perpetually has a young Flynn's likeness, in contrast to Flynn himself physically aging within the Grid. CLU actually succeeds in usurping control of the Grid and making Flynn a fugitive for hundreds of cycles, and the Fatal Flaw that led to CLU's Face–Heel Turn is that he's perpetually frozen at the mindset Flynn had when he created CLU whereas Flynn himself adapts and learns. CLU even briefly smacks down the aged Flynn and actually has a chance to kill Flynn but doesn't take it.

Literature

In The Chronoliths Big Bad Adam Mills is a former teenage psychopath and is still young enough to be protagonist Scott Warden's son (he is, in fact, his stepson).
Discworld:
- Sourcery, with the child Coin as the antagonist and adult wizards like Rincewind as the protagonists. Of course, behind Coin is his father, who died of what seems to be at least partly old age at the start of the story...
- In Reaper Man, there's Death — a compassionate Grim Reaper who treats reaping souls of the dead as a mere job someone has to do — coming to blows with New Death who, on the contrary, delights in it.
In The Expanse novel Persepolis Rising, the point-of-view characters include the crew of the Rocinante — who have saved the day already many times before and at that point are already over 70 years old — considering retirement just as they get trapped on Medina thanks to Laconian forces finally rearing their authoritarian heads and appointing Santiago Singh — a man about 40 years old — as a proud new governor of that key Space Station. In the climax, Singh has a face-to-face encounter with James Holden, the captain of Rocinante who tells him bluntly he spent a lifetime crusading against totalitarians like Laconia, while Singh is just baffled at the idea his dearest High Consul could ever be fallible.
In A Harvest of War 39-year-old Rhona Thyll is the younger villain to her namesake the 58-year-old protagonist and especially the 96-year-old Mayor's older... heroes.
In The Hellfire Club by Paul Straub, the female protagonist Nora is around 49 years old. And the Affably Evil Serial Killer villain, Dick Dart, is more than ten years younger than her. Of course, he always had a thing for older women...
In Night Watch book Twilight Watch, Anton's antagonist turns out to be his much younger former neighbor vampire Kostya.
In 20 Years After, the sequel to The Three Musketeers, we have Mordaunt (who's in his early twenties) against the titular Musketeers and Lord de Winter (all of them at least in their forties) who killed his mother.

Live-Action TV

Ahsoka: Shin's the younger villain to Ahsoka and Sabine's older hero as she was born after the Great Jedi Purge while Ahsoka was active sometime during the Purge and survived it while Sabine was born a year or two before it happened.
The Dominion's enforcers in Deep Space Nine the Jem'Hadar and the Vorta are genetically engineered and are capable of being front line soldiers and diplomats/administrators, respectively, within a couple days of birth. Both are frequently pitted against the Starfleet protagonists who are in their early-mid 30s. Retirement age for a Jem'Hadar is 20.
Doctor Who: In multiple stories, the Doctor, who is Really 700 Years Old even in their younger-looking incarnations, faces off against villains who are much younger than they are. Some particularly good examples:
- "The Sontaran Stratagem"/"The Poison Sky" has arrogant former Teen Genius Luke Rattigan, who is in his early twenties at the oldest. And as for the clone Sontarans, it would be revealed a few series later that they consider living to 12 a long time, so they're not that old either.
- "Kerblam!": Charlie, the apparently friendly young janitor, is in fact a hacker and alleged activist who plots to kill thousands of innocent people via explosives in their Kerblam! orders.
The Falcon and the Winter Soldier: Sam Wilson and Bucky Barnes fight against a terrorist group called the Flag Smashers, led by Karli Morgenthau, who is only a teenager.
In season 3 of Hanna, Marissa appears to be in her 40s while Dragon-in-Chief antagonist Brianna Stapleton appears to be early to mid 30s.
Murdoch Mysteries: James Gillies, the arch-villain of the show, is a university student in his debut episode, and would therefore be around 20 years old in Season 2. Detective William Murdoch, on the other hand, is approaching middle age.
Nashville:
- Appears inverted but not so gloriously subverted with Rayna's (eventual ex) husband Teddy and her father Lamar. Since both are Corrupt Corporate Executives, Teddy at first was being presented as A Lighter Shade of Black. Eventually, their feud reaches Evil Versus Evil territory. In the end, Teddy watches Lamar die of a heart attack in season 2 and Teddy himself is arrested at the end of season 3.

Professional Wrestling

The Living Legend Bruno Sammartino vs. evil apprentice Larry Zbyszko in 1980.
The hardcore legend Terry Funk vs. the nihilistic Raven, from the original ECW.
The younger outsider Chris Candido vs. company founder and business pioneer Carlos Colon at WWC.
The Undertaker vs. Kane with Kane being the antagonistic little brother. Inverted in 1999.
The main shtick of the Shawn Michaels vs. Chris Jericho feud in WrestleMania XIX. As Jericho lost faith in Michaels.
Most of John Cena's feuds during his 2003 Heel run were against older, veteran wrestlers such as Kurt Angle, The Undertaker, Chris Benoit, and Eddie Guerrero.
During his "Legend Killer" days, Randy Orton challenged older, veteran Faces. He specifically feuded with the likes of Mick Foley, Shawn Michaels, Chris Benoit, The Undertaker and Hulk Hogan. Even during his "Viper/Apex Predator" gimmick, he feuded with his former mentor Triple H. His rival John Cena is also three years older.
The aged but locally popular challenger Jerry Lynn vs the younger, cocky foreign champion Nigel McGuinness in Ring of Honor...though the fans seemed to be cheering for Lynn out of sympathy, as they started to turn on him when he actually won the belt from McGuinness.
Rare three-alignment example: Tommy Dreamer (Old Hero) vs. Jack Swagger (Young Villain) vs. Christian.
Yoshihiro Tajiri vs a good deal of the roster in his SMASH promotion but The Triple Tails specifically targeted him for his age. However, their first targets were Yusuke Kodama and Makoto, who were both younger than at least one Triple Tail, Kana. Kana changed their targets to "the old men" after Tajiri came to their rescue.
A rather unsuccessful example is Fortune vs. EV2.0 in 2010 TNA. Fortune, the stable crafted by Ric Flair himself to be the best of the current generation of wrestling, was feuding with a group of ECW originals, all over 40 and/or broken down from years of hardcore wrestling, who had explicitly begged Dixie Carter for one last shot at relevancy. AJ Styles and co. would often call out their opponents for being too old for this and needing to move on. The problem was that nobody really wanted to boo Fortune - due to being made up of younger, more dynamic talents, it naturally contained a lot of fan favorites - and EV2.0 was hard to get behind due to regular changes to its membership and repeated cases of infighting.
Dave Finlay vs. Sami Callihan in EVOLVE. In this case, it was the "hero" going after "the villain" in an effort to redeem him.
On March 12th 2012, Cherry had a match at Union Pro Wrestling against her long standing rival, Mio Shirai, with the stipulation being that if Cherry lost, her real age would become public knowledge. Cherry won but the passport that was being used as her proof of age was stolen by GAMI, who was eventually revealed to be older than Cherry.
Team Bad, the younger villain Tag Team vs the 108th District and the Fella Twins in UCW-Zero, not that the latter two were "old" but team bad were teens.
When Seth Rollins betrayed The Shield, he began a long feud with his former stablemates Dean Ambrose and Roman Reigns. Rollins is a year younger than the two.
After turning Heel, Alexa Bliss feuded with older, more experienced wrestlers such as Carmella (4 years older), Bayley (2 years older), Becky Lynch (4 years older), Naomi (3 years older), and Mickie James (12 years older)^note. Interestingly, her first major feud was back when she was a Face with then heel NXT Women's Champion Sasha Banks.
CM Punk's feud with MJF made full use of this trope. As a young wrestling fan, MJF considered Punk his role model, only to become disillusioned with him as he grew older. Much of the feud consisted of MJF hurling abuse, both physical and verbal, at the much older Punk and generally mocking him over his alleged loss of ability.
As of Clash at the Castle 2022, post-Face–Heel Turn Dominik Mysterio becomes the villainous son to Rey's heroic father...which culminated in a match at WrestleMania 39 after Dominik went to extreme lengths dissing Angie (Rey's wife/Dominik's mother).
The Gunn Club (later named The Gunns) would become the villainous sons to Billy's heroic father after turning on their father (and by extension, The Acclaimed) and allying themselves with Stokely Hathaway.

Tabletop Games

While it's hard to find any unambiguously genuine hero in the Crapsack World of Warhammer 40,000, the Horus Heresy backstory does have the God-Emperor facing off against his favorite son Horus, who has become corrupted by the Chaos Gods, with the Horus Heresy eventually culminating in a duel between the Emperor and Horus, resulting in Horus dying and the Emperor sustaining mortal wounds and being kept kept alive by the Golden Throne.

Video Games

Assassin's Creed
- Assassin's Creed: Brotherhood has the 43-year old Ezio Auditore going up against the 26-year old Cesare Borgia, son of Assassin's Creed II Big Bad Rodrigo Borgia.
- In Revelations, Ezio is 6 years older than the real Big Bad Prince Ahmet.
Batman: Arkham Series
- One of the sidequests in Batman: Arkham Origins involves Batman stopping Anarky from bombing other cities where the latter is revealed to be a teenager upon his defeat.
- Batman: Arkham Knight: The Arkham Knight mockingly calls Batman an old man throughout the game. We don't know the Knight's exact age, but he's really Jason Todd, one of Bruce's sidekicks and wards.
Castlevania: Dawn of Sorrow's Julius Mode has 56-year old Julius Belmont fight the forces of Dracula, who's in the body of a 19-year old.
Danganronpa Another Episode: Ultra Despair Girls has teenage Komaru going up against the elementary school aged Warriors of Hope.
Urizen from Devil May Cry 5 is literally only a month old when he planted the Qliphoth Tree in the human world yet he already has enough power to curb-stomp the likes of the significantly older Dante, Trish, Lady and Nero.
Die Hard: Vendetta, a non-canon game based on the franchise of the same name, sees John McClane considerably aged (his character models have visible grey hair in cutscenes) since the last time he kicked terrorist ass years ago. The main villain, on the other hand, is the son of Hans Gruber from the original movie, with his henchman being the ex-movie star-turned-dragon who couldn't be older than forty.
Final Fantasy
- In Dirge of Cerberus, we've got Vincent, our Woobie Anti-Hero, who's 27 physically but had been asleep (which probably means suspended animation) for thirty years, give or take a few, when the original game took place, so he was 57 then. Dirge of Cerberus takes place 3 years later, which makes him 60 chronologically. Now throw in a 25-year-old Omnicidal Maniac who's possessed by a mad scientist assumed to be older chronologically than Vincent himself.
- The crux of the Archaeology Studium quests in Final Fantasy XIV is the conflict between Professor Rurusha and her younger peer, Namono Tayamono. The latter considers her research into relics based on Gut Feelings to be a complete waste of time and resources, seeking to force her into retirement. For her part, Rurusha just keeps doing what she's doing, asking the Warrior to help her restore what she believes is an ancient mammet with special powers.
Fire Emblem
- In the prologue of Fire Emblem Echoes: Shadows of Valentia, Mycen, an elderly knight and Alm and Celica's adoptive grandfather, fights Slayde, a much younger knight of Zofia, to defend Alm, Celica and the other children of Ram Village.
- In Fire Emblem: Genealogy of the Holy War, the main villain of part 2, Julius, is younger than Seliph.This is actually plot-relevant since Julius is Seliph's younger half brother on his mother's side.
- In the Conquest route of Fire Emblem Fates, the Final Boss is Takumi; the little brother of Corrin
- In Fire Emblem Heroes, the first Arc Villain of the story, Princess Veronica of Embla, is 13, whereas the opposing Prince Alfonse and Princess Sharena of Askr are in their teens. The latter even calls Veronica a "brat."
- In the Azure Moon route of Fire Emblem: Three Houses, the Big Bad is Byleth's former student Edelgard.
In God of War (PS4), we have Kratos, who is physically 50, but is likely a couple of centuries old, vs The Stranger, the Norse God Baldur, who appears to be in his 20s physically, but may at most be 2 centuries old.
Henry Hatsworth in the Puzzling Adventure: Henry Hatsworth looks to be quite a bit older than his rival, Weasleby. He's definitely older than Cole.
Kingdom Hearts: Birth by Sleep has Vanitas who is chronologically 4 years old while in a 15 year old body against Ventus (who are both the same age) along with Aqua (who is 18 years old during that game).
Like a Dragon has several examples throughout the game, even if downplayed.
- Yakuza 2 has Ryuji Goda as the younger villain (30 years old) with an 8 year age gap with the older hero Kiryu Kazuma (38 years old).
- Yakuza 3 has Yoshitaka Mine as the younger villain (33 years old) with a 7 year age gap with the older hero Kiryu Kazuma (40 years old).
- Yakuza 4 has two, actually.
  - Takeshi Kido (30 if we follow actor's age) as the younger villain with a 15 year age gap with Taiga Saejima (45 years old) the older hero.
  - Daigo Dojima (33) as younger villain, with an 8 year age gap with older hero Kiryu Kazuma (41 years old).
- Yakuza 5 has the an incredibly downplayed version of this trope with Shinada at 37 and Baba at 30, with a measly (at least by this trope's standards) 7 year age gap.
- Yakuza 6 features older hero Kiryu Kazuma (48 years old) against one of the game's younger antagonistic Patriarchs, Takumi Someya (stated to be in his early 30s according to his biography).
LISA: The Painful has Brad Armstrong, a bald and aging man. The Big Bad who keeps giving him Sadistic Choices, Buzzo (real name Bernard), is a lot younger than Brad, being Brad's student who trashed the dojo, and mutilated the Final Boss Rando (real name Dustin), another student, who considered Brad as a Parental Substitute.
The eponymous Mega Man X and his best friend Zero were sealed in cold sleep and both wake up during a time where robots based from the former are going rogue.
With the exception of Ocelot and Big Boss, the only guys even older than Snake, Snake in Metal Gear Solid 4: Guns of the Patriots is easily the senior of everyone he fights. And that was before he started to succumb to Rapid Aging. Big Boss and Ocelot themselves were this respectively during Metal Gear Solid 3: Snake Eater as the former is a decade older than the latter.
In a scenario in Advance Wars II: Black Hole Rising, Smug Snake Adder goes up against Old Master Sensei and starts taunting him concerning his age — shortly before he is soundly whipped by the older and more experienced army commander. Only then does Adder recall the stories of a commanding officer in the Yellow Comet army from many years ago who was said to be unstoppable...
No More Heroes III: A 39-year-old Travis Touchdown battles Prince FU, an alien criminal who is at least a couple of years younger than he is.
The Orion Conspiracy: Devlin McCormack is the older protagonist and Captain Shannon is the younger antagonist. The antagonist even insults Devlin's age at one point.
In Persona 5 Strikers:
- The Monarch of the fifth Jail the Phantom Thieves (a group that consists of several high schoolers, two college students and a police officer) invade is Akane Hasegawa, a middle schooler and Zenkichi's daughter. The Monarch isn't evil, and is being used by the main villains, but her resentment toward her father makes the Shadow far more antagonistic than Futaba was in the previous game.
- At the end of the game, Sophia, a prototype AI Ichinose created, goes up against EMMA, whom Ichinose created later.
In Professor Layton and the Unwound Future, Layton goes up against Clive, a young boy he saved 10 years ago and who is plotting to destroy London in revenge for his parents' dying as a result of a failed lab experiment.
In Sekiro: Shadows Die Twice during the Shura ending, Wolf as the Villain Protagonist fights against the significantly older Hero Antagonist Isshin Ashina who is currently hours away from dying of old age as the latter becomes the ending's Final Boss in his attempt to stop Wolf from becoming Shura.
Soulcalibur:
- Tira in Soulcalibur VI is one of the younger characters and is a Serial Killer, making her generally the younger villain vs any of the good characters in a match. Unless her opponent is Talim or Xianghua however, as both are one-to-two years younger.
Streets of Rage 4 takes place around ten years after the original trilogy, and as such the returning trio from the first game are now in their mid-thirties. They square off against the Y twins, the young adult children of Mr. X.
In Space Channel 5 Part 2, Ulala —who is 22 years old— takes on Purge, who is only 18 years old.
Tekken:
- Although it's more a case of Evil Versus Evil, Tekken 7 takes place from Heihachi's perspective as he tries to take down his son, and paints him overall in a more sympathetic light than any earlier entry in the series has.
- Meanwhile, Tekken 6 provides a downplayed example, with the 21-year old Jin, now the antagonist (sort of), squaring off with the new protagonist Lars, who is in his thirties.
Any Uncharted game in which Nate and his father figure Sully are going up against the villains together, there's a good chance that at least one of the villains will be closer to Nate's age than Sully's. The most prominent case of this, however, is Rafe Adler in Uncharted 4: A Thief's End. When Nate and his long-lost brother Sam are pulling off a heist at the Rossi black market auction, Nate instructs Sully to mingle with the guests and distract Rafe, who's bidding on the same cross that they're trying to obtain. Rafe is around Nate's age, but looks younger than that, and is a Psychopathic Manchild to boot, and he openly threatens to kill Sully if he bids on the St. Dismas cross, calling him "old man" as well. Needless to say, Sully's perfectly happy to ruin Rafe's day.
The Witcher: Geralt is close to a century old in the first game, and while he's an alchemically-enhanced monster hunter most of the villains are ordinary humans or short-lived animals. This of course doesn't apply to the main villains of the trilogy, who are long-lived elves.
World of Warcraft:
- In Wrath of the Lich King, the Lich King's nemesis Tirion is older than Arthas by several decades.
- In Battle for Azeroth, Saurfang, an aging warrior, is up against Sylvanas, who looks like she's in her twenties or thirties, but is in reality a millennia-old undead elf.

Visual Novels

Ace Attorney:
- In Phoenix Wright: Ace Attorney – Justice For All, 25-year old Phoenix's main adversary in court is Franziska von Karma, an 18-year old Child Prodigy prosecutor.
- In Apollo Justice: Ace Attorney, there's Phoenix vs. Klavier. While "villain" isn't entirely accurate for Klavier, Phoenix ended up facing the much younger prosecutor in his last case before being disbarred, and ended up underestimating him.
- In Spirit of Justice, a now 35-year old Phoenix faces off against an even younger adversary in court: Rayfa Padma Khura'in, the 14-year old mystic princess of the Khura'in kingdom, as well as prosecutor Nahyuta Sahdmahdi, who's 25.
- In Ace Attorney Investigations 2: Prosecutor's Gambit, Edgeworth is in his late twenties, and the Big Bad, Simeon Saint, is around 24.

Web Animation

BIGTOP BURGER: Steve, the Cloudcuckoolander proprietor of Bigtop Burger, is older than his employees by a significant amount (simplified to "Steve is" by Worthikids). His business rival is Cesare, a younger-looking man who has used his employees to try to kill him. Their respective backstories exaggerate this; Steve is millions of years old and landed on Earth near the end of the Late Devonian Epoch, while Cesare was trying to capture him for years and has been active as a Revenant Zombie for at least a millennium.

Webcomics

The Reveal at the end of the "A Mushroom Kingdom Carol" Story Arc in Brawl in the Family, which explained why the Big Bad of that arc was so strong compared to The Hero. The Bowser that the aging Mario fought wasn't his old rival, but a now adult Bowser Junior. Upon realizing this, Mario takes advantage of his childhood fear of water that he put in him.
"Years of therapy, wasted!"
One-Punch Man: Older hero Silverfang fights against the younger villain and also his former protégé Garou.
The midpoint of Season 1 in The Warrior Returns sees surviving Warriors from previous summonings coming out of hiding to face the newest generation of Warriors and save the world. "The Old Guard" includes Saint Damien Arcadius, the Faith Warrior of the 14th Century, Marie Stevenson, the Transformation Warrior of the 20th Century, and Ivan Pushkin, the Glacial Warrior of the 20th century. They each face their 21st century counterparts with the exception of Ivan, who stands at Russia's border to impede Minsu's advance across Asia.
In Weapon Brown there are Chuck "Weapon" Brown, the (anti-)hero, and CAL-v.1N, the villain. Both of them are cybernetically enhanced Super Soldiers created by the villainous Syndicate, but Chuck is an older model who has been living out in the hellish post-apocalyptic world for quite some time, while CAL is a newer, more advanced model who is physically a good deal younger than Chuck due to having spend quite some time in the Syndicate's storage as a Human Popsicle. Eventually, it turns out that while some of CAL's enhancements might be superior to Chuck's (such as a better Healing Factor and quicker reflexes for instance), Chuck's experience with the post-apocalyptic world gives him quite the edge in the end.
Chuck: (after getting the drop on CAL who was distracted by a walking, headless corpse) Shoulda done a tour of the wastes, punk. After you've watched a man and a woman come to blows over which of them gets to eat their baby, nothing much surprises you.

Western Animation

Duke Igthorn of Adventures of the Gummi Bears is obviously a lot younger than his primary rival and target King Gregor, whose kingdom he's always trying to conquer, and usually calls him "old man" whenever they cross swords.
In Avatar: The Last Airbender, older brother Zuko faces off with younger sister Azula in the series finale, complete with vibes of Obi-Wan and Anakin in the prelude.
Multiple episodes of Batman Beyond have 80-year-old Bruce Wayne taking on younger villains: The Jokerz, Inque, The Ts, Big Time, etc.
In Danny Phantom, Youngblood's spunky, immature attitude clashes with Danny's teenage maturity. This becomes key in one episode. Because Youngblood can only be seen by children, Jazz doesn't realize he exists because she thinks like an adult despite being sixteen. Danny however, takes inspiration from Youngblood's bratty, childish behavior and starts behaving like an Annoying Younger Sibling, causing Jazz to start throwing a tantrum and embracing her childhood, and more importantly, allowing her to spot Youngblood. She then helps Danny kick his ass.
In most stories involving Scrooge McDuck's animated appearances, his rivalries listed above usually still stand, The Beagle Boys and Magica De Spell most notably. However, DuckTales (2017) made some alterations that either give him new younger arch enemies, change some enemies to fit this trope, or change other enemies to no longer fit the trope:
- Flintheart Glomgold appears around Scrooge's age, but he was actually given a notable Age Lift. The two first encountered each other when Glomgold was a child in South Africa going by the name Duke Baloney. Since his goal in life became to be better than Scrooge in literally every way, he included being a better old Scottsman. He wears a fake grey beard and took accent lessons just to seem around Scrooge's age and origin. When he got amnesia and started growing an actual beard, it was a very thick, black color, proving that he is not even close to Scrooge's very old age.
- A character to represent the billionares of the 21st century, Mark Beaks is a tech billionaire who made his money on popular technology, including smartphones, headphones, multiple apps, and crazy weird inventions, many which turn out to all be a hoax. Along with not making a lot of his money square, his hipster lingo and caring way more about buzz and positive publicity than actual money annoys Scrooge (and even Glomgold) to no end.
- A bizzare adaptational inversion to this is John C. Rockerduck. Unlike in the Life and Times of Scrooge McDuck, where Rockerduck was a little Spoiled Brat to Scrooge when his tycoon-owning father was befriending him, he was instead an adult during the gold rush like Scrooge and Goldie were. He was more of a Composite Character of his original self and his father: still a bratty jerkass, but he is already a successful (but far more dishonest) businessman by the time he and Scrooge meet. And he's not gone in the present day either. He too preserved himself thanks to F.O.W.L. preserving him Human Popsicle style.
- Even Ma Beagle, who is clearly very old compared to many other characters in the cast, is definitely much younger than Scrooge —who is around the age of 150 years old due to finding ways to extend his life— having been seeking revenge on him ever since he was able to get the deed to Duckburg from Grandpa Beagle.
Parodied in Futurama with Professor Farnsworth's nemesis Ogden Wernstrom, a former student turned rival of his who mocks the professor for being a senile old has-been, while Farnsworth considers him an impudent young upstart. However, both of them are currently elderly geezers, as Wernstrom is a "mere" 120 years old compared to Farnsworth at 160.
Wernstrom: Go home before you embarrass yourself, old man! Now if you'll excuse me, I'm going to take a nap before the ceremonies.
An episode of Gargoyles has Hudson and an injured Goliath playing cat and mouse with a gun-toting Demona. Hudson's plan is eventually revealed to be: hide just out of sight and let her yammer on till the sun came up. Despite what it looks like, this is actually something of an inversion — Demona is really several centuries older than Hudson, thanks to magical eternal youth on her part and a case of suspended animation on his, so she has both the advantage of centuries of experience without the disadvantages of aging. Hudson's victory is instead thanks to Demona's Immortal Immaturity. Whereas Demona has spent her centuries in a vicious cycle of rage, distrust and betrayal, Hudson made peace with life and found wisdom.
Hudson: I know how to wait.
In Gravity Falls, Stan Pines, a man old enough to be a great uncle, has a business rivalry that later turns violent with Li'l Gideon Gleeful, a nine-year old.
In the first episode where he appears, the 16 year-old Golden Guard in the The Owl House fought against the much older Eda who is confirmed by Word of God to be in her 40s (and physically even older as a result of the curse) with the only reason he gained the upper hand is due to the latter losing her own magic due to the curse. Note that this does not apply to any of his subsequent appearances as every opponent he faced afterwards as a villain happened to be either heroic 14-year olds or against older opponents in an Evil Versus Evil situation.
The Starter Villain for the 5th season of Samurai Jack has the eponymous samurai approximately in his 20s (plus 50 years of being trapped in the future) against the seven Daughters of Aku all who looks to be in their late teen years.

Older Hero vs. Younger Villain

Examples:

Alternative Title(s): Younger Villain Vs Older Hero, Older Hero Versus Younger Villain

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