Rise to Success: Career Highlights of Sylvester Stallone
Discover the career path of Sylvester Stallone, from the first major opportunity to industry-changing achievements.
Sylvester Stallone is a celebrated American actor and filmmaker whose career spans over five decades. He's received numerous awards, including a Golden Globe and a Critics' Choice Award, along with multiple Academy Award and BAFTA nominations. Notably, Stallone is one of only two actors to have starred in a box-office number one film across six consecutive decades, solidifying his lasting impact on the film industry.
1983: Directing Staying Alive
In 1983, Sylvester Stallone directed "Staying Alive", the sequel to "Saturday Night Fever". Although the film was a critical failure, it was a commercial success, opening with the biggest weekend gross for a musical film at the time and ranking among the top ten most financially successful films of 1983.
1984: Starring in Rhinestone
In 1984, Sylvester Stallone co-wrote and starred in the comedy film "Rhinestone" alongside Dolly Parton, where he played a wannabe country music singer. He also performed a song for the movie's soundtrack and regretted turning down a role in "Romancing the Stone" to do Rhinestone.
1985: Signed for Angels with Dirty Faces remake
Around 1985, Sylvester Stallone signed on for a remake of the 1939 film "Angels with Dirty Faces" as part of a deal with Cannon Films, but the project was met with disapproval and ultimately shelved in favor of the action film "Cobra".
1985: Success with Rocky IV and Rambo: First Blood Part II
In 1985, Sylvester Stallone continued his success with the Rocky and Rambo franchises with Rocky IV and Rambo: First Blood Part II. Stallone met Franco Columbu to develop his character's appearance for the film Rocky IV. Both films were major financial successes.
1986: Release of Cobra and Establishment of White Eagle Enterprises
In 1986, Cannon Films opted to produce the action film "Cobra" instead of the remake of "Angels with Dirty Faces" with Sylvester Stallone. "Cobra" became a box-office success, leading to the creation of Stallone's production company, White Eagle Enterprises.
1987: Starring in Over the Top
In 1987, Sylvester Stallone starred in "Over the Top," a family drama about a trucker in an arm wrestling competition. The film was poorly received by critics and failed at the box office.
1989: Co-starring in Tango & Cash
In 1989, Sylvester Stallone co-starred with Kurt Russell in the buddy cop action film "Tango & Cash," which was a solid box office success, grossing over $120 million worldwide.
1992: Appearing in Stop! Or My Mom Will Shoot
In 1992, Sylvester Stallone appeared in the action comedy "Stop! Or My Mom Will Shoot", which was a critical and box-office disaster. Stallone took the role because he heard that Schwarzenegger was interested in the lead.
1993: Comeback with Cliffhanger and Starring in Demolition Man
In 1993, Sylvester Stallone made a comeback with the action thriller "Cliffhanger", which was a box office success. Later that year, he starred in the futuristic action film "Demolition Man" with Wesley Snipes and Sandra Bullock, which was also successful.
1994: Political Contribution to Rick Santorum
In 1994, Stallone contributed $1,000 to the campaign of then-Congressman Rick Santorum, who was running for the Senate in Pennsylvania.
1994: Starring in The Specialist
In 1994, Sylvester Stallone starred in "The Specialist" alongside Sharon Stone. While the critical reception of the movie was overwhelmingly negative, the film was a commercial success.
1995: Starring in Judge Dredd
In 1995, Sylvester Stallone starred as the title character in the science fiction action film "Judge Dredd", which had a poor domestic box-office performance, but was saved by its overseas appeal. Stallone also signed a three-picture deal with Universal Pictures for $60 million.
1996: Starring in Daylight
In 1996, Sylvester Stallone starred in the disaster film "Daylight" as a former emergency services chief. While it underperformed at the domestic box office, it did better overseas and grossed $158 million worldwide.
1997: Starring in Cop Land
In 1997, Sylvester Stallone starred in the crime drama "Cop Land" alongside Robert De Niro and Ray Liotta. The film was critically well-received and Stallone's performance earned him the Stockholm International Film Festival Best Actor Award.
1998: Voice-over work for Antz
In 1998, Sylvester Stallone did voice-over work for the animated film "Antz", which was a success domestically.
2000: Starring in Get Carter
In 2000, Sylvester Stallone starred in the thriller "Get Carter", a remake of the 1971 British film of the same name, which was poorly received by both critics and audiences. Stallone's career declined considerably after this film.
2001: Starring in Driven
In 2001, Sylvester Stallone starred in Driven, which was a critical and commercial failure, further contributing to a decline in his career.
2002: Starring in Avenging Angelo and D-Tox
In 2002, Sylvester Stallone starred in Avenging Angelo and D-Tox, both of which were critical and commercial failures, further contributing to the decline of his career.
2003: Role in Spy Kids 3-D: Game Over
In 2003, Sylvester Stallone played a villainous role in "Spy Kids 3-D: Game Over", which was a huge box-office success. He also had a cameo appearance in the French film "Taxi 3" and started to regain prominence for his supporting role in the neo-noir crime drama "Shade".
2005: Co-presenter of The Contender, Guest Appearance in Las Vegas, Induction of Hulk Hogan into WWE Hall of Fame, and Release of Sly Moves
In 2005, Sylvester Stallone co-presented the NBC reality television boxing competition series "The Contender". He made a guest appearance in two episodes of the television series "Las Vegas", inducted Hulk Hogan into the WWE Hall of Fame, and released his book "Sly Moves", a fitness and nutrition guide with insights into his life.
2006: Comeback with Rocky Balboa
In 2006, Sylvester Stallone had a comeback with the sixth installment of the Rocky series, "Rocky Balboa", which he wrote, directed and starred in. The film was a critical and commercial hit. Also in 2006, Stallone began development of a Death Wish remake, but later relinquished the role.
January 25, 2008: Release of Rambo
On January 25, 2008, Sylvester Stallone reprised his role as Rambo with the fourth installment of the film franchise, titled simply "Rambo", which opened in theaters and grossed $6,490,000 on its opening day.
July 2009: Cameo Appearance in Kambakkht Ishq
In July 2009, Sylvester Stallone made a cameo appearance in the Bollywood film "Kambakkht Ishq", playing himself.
August 13, 2010: Release of The Expendables
On August 13, 2010, The Expendables, written, directed, and starring Sylvester Stallone, was released. The film took $34,825,135 in its opening weekend, going straight in at No. 1 in the US box office and marking the biggest opening weekend in Stallone's career.
August 17, 2012: Release of The Expendables 2
On August 17, 2012, The Expendables 2 was released. The sequel received a positive critical reception of 67% on Rotten Tomatoes, as opposed to the original's 41%.
2013: Starring in Bullet to the Head, Escape Plan, and Grudge Match
In 2013, Sylvester Stallone starred in the action film "Bullet to the Head", the action thriller "Escape Plan", and the sports comedy drama "Grudge Match".
August 15, 2014: Release of The Expendables 3
On August 15, 2014, The Expendables 3 was released. The film was negatively received by both critics and audiences and became the lowest-grossing film in the series.
2023: Donation to Kyrsten Sinema and Meeting with Pope Francis
In 2023, Stallone donated $11,600 to independent Senator Kyrsten Sinema's re-election campaign in Arizona. Later that year, he and his family spent time with Pope Francis in a private meeting at the Vatican.
January 16, 2025: Appointment as Special Ambassador to Hollywood
On January 16, 2025, it was announced that Stallone would serve as a Special Ambassador to Hollywood, alongside Jon Voight and Mel Gibson. This appointment made by Trump was aimed at strengthening Hollywood and reclaiming business lost to foreign countries.
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