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 highly successful American actor, painter, and filmmaker with a career spanning over five decades. He's received numerous awards, including a Golden Globe and Critics' Choice Award, and has been nominated for multiple Academy Awards and BAFTA Awards. Notably, he's one of only two actors to have starred in a #1 box-office film across six consecutive decades. His films have collectively grossed over $7.5 billion worldwide, demonstrating his enduring popularity and box-office appeal.
1983: Directing Staying Alive
In 1983, Sylvester Stallone directed "Staying Alive", the sequel to "Saturday Night Fever" starring John Travolta. Though a critical failure, it achieved commercial success, grossing nearly $65 million in the US box office against a $22 million budget and ranking among the top ten financially successful films of the year.
1984: Starring in Rhinestone
In 1984, Sylvester Stallone co-wrote and starred alongside Dolly Parton in the comedy film "Rhinestone", playing a wannabe country music singer. He also performed a song for the movie's soundtrack and turned down a role in "Romancing the Stone" to make "Rhinestone".
1985: Signing up for Angels with Dirty Faces remake
Around 1985, Sylvester Stallone signed on to a remake of the 1939 film "Angels with Dirty Faces" as part of a multi-picture deal with Cannon Films. The remake faced disapproval and was eventually replaced with 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, releasing "Rocky IV" and "Rambo: First Blood Part II". He prepared for his role in Rocky IV by training with Franco Columbu, and both films were major financial successes.
1986: Release of Cobra and formation of White Eagle Enterprises
In 1986, the action film "Cobra" was released and became a box-office success after the remake of "Angels with Dirty Faces" was cancelled. This success led to Sylvester Stallone setting up his production company, White Eagle Enterprises.
1987: Starring in Over the Top
In 1987, Sylvester Stallone starred in "Over the Top", a family drama where he played a struggling trucker in an arm wrestling competition. The film was poorly received by critics and was a box-office failure.
1989: Co-starring in Tango & Cash
In 1989, Sylvester Stallone co-starred with Kurt Russell in the buddy cop action film "Tango & Cash", which grossed over US$120 million worldwide.
1992: Appearing in Stop! Or My Mom Will Shoot
In 1992, Sylvester Stallone appeared in Roger Spottiswoode's action comedy "Stop! Or My Mom Will Shoot", which was a critical and box-office disaster. Stallone took the role based on a rumor that Arnold Schwarzenegger was interested in it.
1993: Comeback with Cliffhanger and Demolition Man
In 1993, Sylvester Stallone made a comeback with Renny Harlin's action thriller "Cliffhanger", and starred in the futuristic action film "Demolition Man" with Wesley Snipes and Sandra Bullock, both of which were commercially successful.
1994: Donation to Rick Santorum
In 1994, Stallone donated $1,000 to Republican Congressman Rick Santorum's Senate campaign.
1994: Starring in The Specialist
In 1994, Sylvester Stallone starred in "The Specialist" alongside Sharon Stone, directed by Luis Llosa. Despite negative reviews, it was commercially successful, making back its budget.
1995: Starring in Judge Dredd
In 1995, Sylvester Stallone played the title character in the science fiction action film "Judge Dredd". Despite a poor domestic box-office performance, its overseas appeal helped it make back its budget.
1996: Starring in Daylight
In 1996, Sylvester Stallone starred in the disaster film "Daylight" as a disgraced former emergency services chief. Although it underperformed domestically, it grossed a total of $158 million worldwide.
1997: Starring in Cop Land
In 1997, Sylvester Stallone starred in the crime drama "Cop Land" as an overweight sheriff alongside Robert De Niro and Ray Liotta. The film was critically well-received and was a modest success at the box office, earning Stallone 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.
February 2000: Expiration of Universal Pictures deal without payment
In February 2000, the three-picture deal Sylvester Stallone signed with Universal Pictures for $60 million expired without him making any films. As a result, he received no payment from the deal.
2000: Starring in Get Carter remake
In 2000, Sylvester Stallone starred in "Get Carter", a remake of the 1971 British film. However, the film was poorly received by both critics and audiences.
2001: Decline in career after Driven
After starring in Get Carter in 2000, Sylvester Stallone's career declined considerably in 2001 after his subsequent film, "Driven", was a critical and commercial failure.
2002: Critical and commercial failures of Avenging Angelo and D-Tox
In 2002, Sylvester Stallone's films "Avenging Angelo" and "D-Tox" were both critical and commercial failures, continuing 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 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 crime drama "Shade".
2005: Co-presenting The Contender and WWE Hall of Fame Induction
In 2005, Sylvester Stallone co-presented the NBC reality television boxing competition series "The Contender" with Sugar Ray Leonard. He also made a guest appearance in two episodes of "Las Vegas", inducted Hulk Hogan into the WWE Hall of Fame, and released his fitness and nutrition book "Sly Moves".
2006: Desire to direct The Forty Days of Musa Dagh
In 2006, Sylvester Stallone expressed his desire to direct a film about Musa Dagh, adapted by Franz Werfel's novel "The Forty Days of Musa Dagh,” detailing the genocide of its Armenian community in 1915.
2006: Comeback with Rocky Balboa
In 2006, Sylvester Stallone had a comeback with the sixth installment of the Rocky series, "Rocky Balboa", which was a critical and commercial hit. He also began developing a remake of the 1974 film "Death Wish", but later passed on the project.
January 25, 2008: Rambo released in theaters
On January 25, 2008, Sylvester Stallone reprised his role in the fourth installment of the Rambo franchise, titled simply "Rambo". The film grossed US$6,490,000 on its opening day.
2008: Endorsement of John McCain
In 2008, Stallone endorsed John McCain for the year's presidential election.
July 2009: Cameo appearance in Kambakkht Ishq
In July 2009, Sylvester Stallone made a cameo appearance in the Bollywood film "Kambakkht Ishq", where he played himself.
2009: Filming of The Expendables
In 2009, Sylvester Stallone filmed "The Expendables", which was released on August 13, 2010. The movie was written, directed by, and starring Sylvester Stallone. Joining him in the film were fellow action stars Jason Statham, Jet Li, and Dolph Lundgren, as well as Terry Crews, Mickey Rourke, Randy Couture, Eric Roberts, and Stone Cold Steve Austin, and cameos by fellow '80s action icons Bruce Willis and Arnold Schwarzenegger.
2009: Reconsidering Death Wish remake
In 2009, Sylvester Stallone stated that he was again considering the project of Death Wish remake after announcing in 2006 that he was no longer involved. However the role went to Bruce Willis with Eli Roth as director.
August 13, 2010: Release of The Expendables
On August 13, 2010, "The Expendables", written, directed by, and starring Sylvester Stallone, was released. The film, which featured several action stars, had the biggest opening weekend in Stallone's career.
2011: Voice of a Lion in Zookeeper
In 2011, Sylvester Stallone provided the voice of a lion in Kevin James' comedy, "Zookeeper".
August 17, 2012: Release of The Expendables 2
On August 17, 2012, "The Expendables 2" was released. The sequel received a positive critical reception compared to the original. As well as returning cast members, the film also included Jean-Claude Van Damme and Chuck Norris.
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", directed by Walter Hill, and in the action thriller "Escape Plan", along with Arnold Schwarzenegger and Jim Caviezel. Also in 2013, he starred in the sports comedy drama "Grudge Match" alongside Robert De Niro. Stallone was credited as writer for the Jason Statham action film vehicle Homefront.
August 15, 2014: Release of The Expendables 3
On August 15, 2014, "The Expendables 3" was released. The film was negatively received and became the lowest-grossing film in the series.
2016: Comments on Donald Trump and NEA Offer
In 2016, Stallone described Donald Trump as a "Dickensian character" and "larger than life" but did not endorse him during the Republican primaries. He also declined an offer to become Chair of the National Endowment for the Arts to focus on veteran issues.
2017: Support for Armenian Genocide Recognition
In 2017, Stallone expressed his support for the recognition of the Armenian genocide and attended the film premiere for 'The Promise', a movie set during the genocide.
2023: Donation to Kyrsten Sinema and Vatican Meeting
In 2023, Stallone donated $11,600 to Senator Kyrsten Sinema's re-election campaign in Arizona. Later that year, he and his family met with Pope Francis at the Vatican.
2024: Attendance at Mar-a-Lago and Praise for Trump
After Trump's win in the 2024 election, Stallone attended an event at Mar-a-Lago. During a speech, Stallone praised Trump as a "mythical character" and the "second George Washington", comparing him to his character Rocky Balboa.
January 16, 2025: Appointment as Special Ambassador to Hollywood
On January 16, 2025, it was announced by Trump that Stallone would serve as a Special Ambassador to Hollywood, along with Jon Voight and Mel Gibson. Trump wants these actors to bring back business lost to "foreign countries".
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