- Expelled from 14 schools for antisocial and violent behavior before he was age 13.
- Birth complications, caused by forceps, resulted in paralysis of the lower left side of his face, manifested by a perennial snarl and slurred speech.
- The Expendables (2010) opened at number one at the U.S. box office with a first weekend gross of $35 million. This makes Sylvester Stallone the only person in Hollywood history to have starred in films that have opened atop the box office charts over five consecutive decades.
- Stallone claims to have been able to bench press 385-400 lbs (174.6-181.4 kg) and squat 500 lbs (226.8 kg) in his prime. While in a bench pressing contest with former Mr. Olympia Franco Columbu, he severely tore his pectoral muscle and needed over 160 stitches on it. This is why one half of his chest is more veiny than the other.
- At age 15, his classmates voted him the one most likely to end up in the electric chair.
- Dislikes his first name, usually referred to as "Sly".
- After seven years of fruitless struggle and with only $115 in the bank, he turned down a $330,000 offer for his Rocky screenplay and earned $230 a week starring in it himself.
- A noted fan of cigar smoking, he quit smoking cigarettes while filming Rocky (1976) when he was thirty after he found himself getting out of breath in the ring.
- The only Hollywood star to have box office hit movies in each of five consecutive decades (1970s-2010s).
- Turned down the title role played by Christopher Reeve in Superman (1978).
- Was part owner of the Planet Hollywood restaurant chain with Bruce Willis and Arnold Schwarzenegger.
- Rocky (1976) is ranked #4 on the American Film Institute's 100 Most Inspiring Movies of All Time.
- He said it was a stroke of good luck that got Rocky (1976) made. He met with the producers to audition for another film, but was turned down for the part. In the course of conversation Stallone said that he was not only an actor, but also a writer. As he started to leave the room, the producers asked him if he was working on any scripts. That's when Stallone pitched them the story for Rocky (1976) and the producers asked to read the script. Stallone has mentioned this anecdote as an example of the adage "Luck happens when preparation meets opportunity.".
- All his children's names begin with the letter "S": Sage, Sargeoh, Sophia, Sistine and Scarlet.
- Stallone was paid a mere $60,000 to do Cop Land (1997). It is said that he did the film to play a serious role and escape his action hero cast type.
- His son, Sage Stallone, was found dead on July 13, 2012 in Los Angeles, California.
- Is good friends with Arnold Schwarzenegger Bruce Willis, Don Johnson, Milo Ventimiglia and Tom Arnold.
- Second son Seargeoh Stallone (born 1979) is autistic.
- His performance as Rocky Balboa in the "Rocky" movie series is ranked #64 on Premiere magazine's 100 Greatest Movie Characters of All Time.
- Attended the University of Miami on an athletic scholarship
- His mother, Jackie Stallone, is a huge fan of Jackie Chan. Chan and Stallone are very good friends.
- In 1991, he sued writer Peter "Taki" Theodoracopulos and the British magazine "The Spectator" for suggesting he acted in a cowardly and hypocritical way when he "ducked the Vietnam War" He won the case.
- Oil paints in his spare time and considers Leonardo Da Vinci his personal hero.
- The 39-year hiatus between his Academy Award nominations (Rocky (1976); Creed (2015)) is a record. The previous record of 38 years was held by Helen Hayes (1931/32; 1970), Jack Palance (1953; 1991) and Alan Arkin (1968; 2006).
- Was said to have only $106 in his bank account at the time the Rocky (1976) project was given the green light by producer Irwin Winkler.
- Mother Jackie Stallone was a huge fan of Tyrone Power and had originally named him Tyrone Stallone, but when she got the birth certificate it had been changed by Sly's father Frank Stallone to Sylvester Gardenzio Stallone.
- On June 5, 1994, he broke up with then-girlfriend Jennifer Flavin by sending her a "Dear Jane" letter via FedEx. They reconciled after one year, on June 5, 1995 and married on May 17, 1997.
- The voice of Lou the policeman in The Simpsons (1989) is based on him.
- According to Anthony Holden's "Behind the Oscar" (New York: Simon & Shuster, 1993), the great Frank Capra was enlisted in the Oscar campaign for the original Rocky (1976). Capra was quoted as saying, "I think it's the best picture in the last ten years. It's got my vote for the Oscars all the way down the line.".
- His father Frank Stallone was a hairdresser and mother Jackie Stallone is a larger-than-life eccentric who has also sought fame as an astrologer and women's wrestling promoter. Her maiden name is Labofish.
- Turned down the roles played by Richard Gere in American Gigolo (1980), An Officer and a Gentleman (1982) and Pretty Woman (1990).
- Born in the charity ward of a hospital in the New York ghetto of Hell's Kitchen. At his birth, the doctor's forceps accidentally severed a nerve in his cheek, leaving him with his trademark droopy mouth.
- He was considered for Patrick Swayze's role in Next of Kin (1989).
- In 1971, he auditioned for a small role in Francis Ford Coppola's The Godfather (1972) but didn't get the role. He decided he might have better luck as a writer. He wrote the screenplay for the modestly successful The Lords of Flatbush (1974) and had a featured role in the film.
- Is a close friend and huge fan of Sir Elton John.
- Dated Janice Dickinson from December 1993 to July 1994. Sly thought that he was the father of her daughter Savannah Rodin, but when he discovered that the real father of girl was Michael Birnbaum, he left her.
- Listed as one of the top heroes of all time by the American Film Institute (AFI) on 2003, he listed seventh behind Gregory Peck, Harrison Ford, Sean Connery, Humphrey Bogart, Gary Cooper and Jodie Foster.
- Moved to Philadelphia in the early 1960s, residing in Frankford and Rittenhouse Square. He went to Lincoln High School but never completed 10th grade. In 1963, he enrolled in the Devereux Manor High School in Berwyn, Chester County, a school for emotionally troubled youths.
- Oscar-nominated a second time in 2016 for his performance as Rocky Balboa in Creed (2015) at age 69, the same age as Burgess Meredith when he was nominated for his performance as Mickey Goldmill in Rocky (1976), and also for playing the coach.
- Along with Barry Fitzgerald and Al Pacino, he is one of only three actors to receive Oscar nominations for both Best Actor and Best Supporting Actor for playing the same character: (1) Fitzgerald was nominated for both awards for playing Father Fitzgibbon in Going My Way (1944), (2) Pacino was nominated for Best Supporting Actor for playing Michael Corleone The Godfather (1972) and Best Actor for the same role in The Godfather Part II (1974) and (3) Stallone was nominated for Best Actor for playing Rocky Balboa in Rocky (1976) and Best Supporting Actor for the same role in Creed (2015).
- In 1988, he was offered $4 million to do an advert for an American beer commercial under the condition that he cut his hair; when he refuse they offered a further $1 million to go to the barber - he still refused.
- In 1986, following the enormous success of Rambo: First Blood Part II (1985), Stallone was received at the White House by President Ronald Reagan.
- He was presented with a certificate of recognition by California Governor Arnold Schwarzenegger for filming Rocky Balboa (2006) in Los Angeles at a time when other filmmakers are moving their business to cheaper states or overseas locations to cut costs (December 22, 2005).
- Has a total of five children: Sage Stallone and Seargeoh Stallone with first wife Sasha Stallone and Sophia Rose Stallone, Sistine Rose Stallone and Scarlet Rose Stallone with third wife Jennifer Flavin.
- His Miami 24,000-square-foot villa and its three guest houses sold after two years on the market for $24 million.
- A lifelong Republican, he is one of President George W. Bush's two favorite actors. The other is fellow action hero and conservative Republican Chuck Norris. Both men attended Bush's inauguration as President in 2001.
- He became a boxing promoter in the 1980s. His boxing promoting company, "Tiger Eye Productions", signed world champion boxers Sean O'Grady and Aaron Pryor.
- Sylvester sued his former business manager, Kenneth Starr, for giving him bad business advice. He claims $17M in damages. Part of the advice was for him to hold onto his shares in Planet Hollywood, the now bankrupt restaurant chain, despite it already being in a financial bind (February 14, 2002).
- He turned down the lead role in Coming Home (1978), which went to Jon Voight and won him an Academy Award.
- Did most of his own singing in the musical comedy Rhinestone (1984).
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