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 an American actor and filmmaker with a career spanning over fifty years. He's received a Golden Globe and Critics' Choice Award, along with multiple Academy Award and BAFTA nominations. Notably, he's one of two actors to star in a box-office number one film across six consecutive decades. His films have grossed over $7.5 billion worldwide, establishing him as a major figure in the entertainment industry.
1968: Role in That Nice Boy
In 1968, while attending the University of Miami, Stallone had a role in the drama "That Nice Boy", also known as "The Square Root".
1969: Moved to New York City and Struggled as an Actor
In 1969, Sylvester Stallone moved to New York City and struggled to find acting work, eventually finding some minor roles.
1969: Worked with John Herzfeld on Horses
In 1969, Sylvester Stallone worked with John Herzfeld on a low-budget, self-produced film called "Horses".
1970: First Starring Role in The Party at Kitty and Stud's
In 1970, Stallone had his first starring role in the softcore pornography film "The Party at Kitty and Stud's", earning $200 for two days of work. He took the role out of desperation after being evicted and becoming homeless.
1970: Minor Film Roles
In 1970, Stallone had minor, uncredited appearances in "M*A*S*H" and "Pigeons".
1970: Started Using the Stage Name Sylvester E. Stallone
In 1970, Sylvester Stallone began using the stage name Sylvester E. Stallone.
November 15, 1971: Erotic play Score performance end
On November 15, 1971, Stallone starred in the erotic off-Broadway stage play "Score" which ran for 23 performances and was later made into the 1974 film of the same name.
1971: Minor Film Roles
In 1971, Stallone had brief appearances in Woody Allen's "Bananas" and the thriller "Klute".
1972: Acting in a play and the role of Stanley in The Lords of Flatbush
From 1972, Stallone acted in a play where an agent in attendance thought that Stallone fit the role of Stanley, a main character in "The Lords of Flatbush", which had a start-stop schedule from 1972 to 1974 over budget issues.
1972: Failed to Get Job in The Godfather
In 1972, Stallone was on the verge of giving up his acting career after failing to get a job as an extra in "The Godfather". He instead got a background role in "What's Up, Doc?".
1973: First Proper Starring Role in No Place to Hide
Around mid-1973, Stallone achieved his first proper starring role in the independent film "No Place to Hide", playing a man associated with a New York-based urban terrorist movement.
1974: Acting in a play and the role of Stanley in The Lords of Flatbush
From 1972, Stallone acted in a play where an agent in attendance thought that Stallone fit the role of Stanley, a main character in "The Lords of Flatbush", which had a start-stop schedule from 1972 to 1974 over budget issues.
1974: Role in The Lords of Flatbush
In 1974, Stallone appeared in the film "The Lords of Flatbush", marking a gradual step in his acting career.
1974: Second Starring Role in The Lords of Flatbush
In 1974, Sylvester Stallone had his second starring role in "The Lords of Flatbush".
1974: Score Film Release
In 1974, the film "Score", in which Stallone starred, was released.
1975: Supporting Roles in Farewell, My Lovely; Capone; and Death Race 2000
In 1975, Stallone played supporting roles in "Farewell, My Lovely", "Capone", and "Death Race 2000". He also made guest appearances on the TV series "Police Story" and "Kojak".
1976: Rocky Release and Fame
In 1976, Stallone gained worldwide fame with his starring role in "Rocky", a sports drama about a struggling boxer. Upon its release, critic Roger Ebert stated that Stallone could become the next Marlon Brando.
1976: Success with Rocky
In 1976, Sylvester Stallone achieved critical and commercial success with his iconic role as Rocky Balboa in "Rocky", a film he also wrote.
1977: Academy Award Nominations
In 1977, Stallone became the third actor in history to be nominated for two Academy Awards for Best Original Screenplay and Best Actor.
1977: Rocky's Academy Award Nominations and Wins
In 1977, at the 49th Academy Awards, "Rocky" was nominated for ten Oscars, including Best Actor and Best Original Screenplay for Stallone. The film won Best Picture, Best Directing, and Best Film Editing. The character was also voted into the International Boxing Hall of Fame.
1978: Directorial Debut with Paradise Alley and Starred in F.I.S.T.
In 1978, Stallone made his directorial debut and starred in the film "Paradise Alley", and he also starred in "F.I.S.T.".
1978: Singing in Paradise Alley
In 1978, Sylvester Stallone sang "Too Close to Paradise" for Paradise Alley, with music provided by Bill Conti.
1979: Rocky II Release
In 1979, Stallone wrote, directed, and starred in "Rocky II", which became a major success, grossing US$200 million.
1981: Starred in Escape to Victory and Nighthawks
In 1981, Stallone starred in "Escape to Victory", and also in the thriller "Nighthawks".
1982: Portrayed John Rambo in First Blood
In 1982, Stallone portrayed John Rambo in "First Blood", initiating his role across five Rambo films.
1982: Starred in First Blood and Rocky III
In 1982, Stallone starred as John Rambo in "First Blood", which launched the Rambo franchise, and he also wrote, directed, and starred in "Rocky III".
1982: Singing "Take Me Back" in Rocky III
In 1982, as Rocky Balboa in Rocky III, Sylvester Stallone sang "Take Me Back" to his on-screen wife, Adrian. The song was originally performed by his brother, Frank Stallone.
1983: Frank Stallone's Hit Song "Far from Over"
In 1983, Frank Stallone's song "Far from Over", for Staying Alive, reached the #10 U.S. hit.
1983: Directing Staying Alive
In 1983, Sylvester Stallone directed "Staying Alive", the sequel to "Saturday Night Fever" starring John Travolta. While the film was a critical failure, it achieved 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 the year.
1984: Starring in Rhinestone
In 1984, Sylvester Stallone co-wrote and starred in the comedy film "Rhinestone" alongside Dolly Parton, playing a wannabe country music singer, and he also performed a song for the movie's soundtrack. Stallone later regretted turning down the lead role in "Romancing the Stone" to make "Rhinestone".
1985: Signing on for Angels with Dirty Faces Remake
Around 1985, Sylvester Stallone was signed to star in a remake of the 1939 film "Angels with Dirty Faces", as part of a multi-picture deal with Cannon Films. Christopher Reeve was set to co-star, and Menahem Golan was to direct. However, the remake faced disapproval, and Cannon Films opted to make the action film "Cobra" instead.
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". For Rocky IV, Stallone trained with Franco Columbu to develop his character's appearance. Both films became major financial successes.
1986: Release of Cobra and Founding of White Eagle Enterprises
In 1986, Cannon Films released the action film "Cobra", starring Sylvester Stallone, which became a box-office success. This led to Stallone setting up his own production company, White Eagle Enterprises.
1986: Acted in Cobra
In 1986, Stallone acted in "Cobra", as one of Hollywood's highest-paid actors.
1987: Starring in Over the Top
In 1987, Sylvester Stallone starred in the family drama "Over the Top" as a struggling trucker who enters an arm wrestling competition. The film was poorly received by critics and was a box-office failure.
1989: Acted in Tango and Cash
In 1989, Stallone acted in "Tango and Cash", as one of Hollywood's highest-paid actors.
1989: Co-starring in Tango & Cash
In 1989, Sylvester Stallone co-starred alongside Kurt Russell in the buddy cop action film "Tango & Cash", which grossed US$57 million in foreign markets and over US$120 million worldwide. Stallone also became a boxing promoter in the 1980s.
1990: A Man Called... Rainbo
In 1990, the film No Place to Hide was re-edited with outtakes and newly shot footage, then redubbed into a parody titled "A Man Called... Rainbo".
1991: Starred in Oscar
In 1991, Stallone starred in the comedy film "Oscar", which had modest success.
1992: Starred in Stop! Or My Mom Will Shoot
In 1992, Stallone starred in the comedy film "Stop! Or My Mom Will Shoot", which had modest success.
1993: Acted in Cliffhanger and Demolition Man
In 1993, Stallone acted in "Cliffhanger" and "Demolition Man", as one of Hollywood's highest-paid actors.
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 also starred in the futuristic action film "Demolition Man" alongside Wesley Snipes and Sandra Bullock, which was also a box office success.
1993: Release of Demolition Man
In 1993, the movie Demolition Man, in which Sylvester Stallone starred, was released.
1994: Acted in The Specialist
In 1994, Stallone acted in "The Specialist", as one of Hollywood's highest-paid actors.
1994: Contribution to Rick Santorum's Campaign
In 1994, Stallone contributed $1,000 to the campaign of then-Congressman Rick Santorum, who was running for the Senate in Pennsylvania.
1995: Starring in Judge Dredd
In 1995, Sylvester Stallone starred in the science fiction action film "Judge Dredd", based on the British comic book "2000 AD". Despite underperforming at the domestic box office, its overseas appeal saved the film from being a complete failure.
1996: Starring in Daylight
In 1996, Sylvester Stallone starred in the disaster film "Daylight" as a former emergency services chief. The film underperformed at the domestic box office but did better overseas.
1997: Starred in Cop Land
In 1997, Stallone starred in the drama "Cop Land", for which he gained weight to play a powerless sheriff.
1997: Starring in Cop Land and Winning Best Actor Award
In 1997, Sylvester Stallone starred in the crime drama "Cop Land" alongside Robert De Niro and Ray Liotta. The film was 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 commercial success domestically.
February 2000: Expiration of Stallone's Three-Picture Deal with Universal Pictures
In February 2000, Sylvester Stallone's three-picture deal with Universal Pictures expired without him making any films. He therefore received no payment, despite signing the $60 million deal in 1995.
2000: Death Race 2000
In 2000, Stallone played supporting roles in "Farewell, My Lovely", "Capone", and "Death Race 2000".
2000: Starring in Get Carter
In 2000, Sylvester Stallone starred in "Get Carter", a remake of the 1971 British film of the same name. The film was poorly received by critics and audiences.
2001: Starring in Driven
In 2001, Sylvester Stallone starred in "Driven", which was a critical and commercial failure, marking 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 impacting his career.
2003: Villainous Role in Spy Kids 3-D: Game Over and Cameo in Taxi 3
In 2003, Sylvester Stallone played a villain in "Spy Kids 3-D: Game Over", which was a box-office success. He also had a cameo in the French film "Taxi 3". That year, Stallone also started to regain prominence for his role in Shade which was praised by critics. Stallone was also set to star and direct Notorious, but the project was shelved.
2005: Co-presenting The Contender, Guest Appearances, WWE Hall of Fame Induction, and Sly Moves Book Release
In 2005, Sylvester Stallone co-presented the NBC reality television boxing competition series "The Contender" alongside Sugar Ray Leonard. He also made guest appearances in two episodes of the television series "Las Vegas". Stallone inducted Hulk Hogan into the WWE Hall of Fame. In August 2005, Stallone released his book "Sly Moves", a guide to fitness and nutrition.
2006: Rocky Balboa Film Release
In 2006, Stallone continued his role as Rocky Balboa with the release of the film "Rocky Balboa".
2006: Comeback with Rocky Balboa and Death Wish Remake Development
In 2006, Sylvester Stallone had a comeback with "Rocky Balboa", the sixth installment of the "Rocky" series, which was a critical and commercial hit. Stallone wrote, directed, and starred in the film. In 2006, the development of the "Death Wish" remake began, with Stallone initially slated to direct and star, but he later became uninvolved.
January 25, 2008: Rambo Release
On January 25, 2008, Sylvester Stallone reprised his role as Rambo in the fourth installment of the franchise, titled "Rambo". The film grossed US$6,490,000 on its opening day.
2008: Rambo Film Release
In 2008, Stallone continued his established role as Rambo with the release of the film "Rambo".
2008: Endorsement of John McCain
In 2008, Stallone endorsed John McCain for that year's presidential election.
July 2009: Cameo in Bollywood Film Kambakkht Ishq
In July 2009, Sylvester Stallone made a cameo appearance as himself in the Bollywood film "Kambakkht Ishq".
2009: Filming of The Expendables
During the summer/winter of 2009, Sylvester Stallone filmed The Expendables.
2009: Stallone Considers Death Wish Project Again
In a 2009 interview, Sylvester Stallone stated that he was again considering the Death Wish project.
August 13, 2010: Release of The Expendables
On August 13, 2010, Sylvester Stallone's film "The Expendables" was released. It was filmed during summer/winter 2009. The film earned US$34,825,135 in its opening weekend, marking the biggest opening weekend in Stallone's career.
2010: The Expendables Film Franchise Launch
In 2010, Stallone launched "The Expendables" film franchise, starring as the mercenary Barney Ross.
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 to a positive critical reception. The film featured returning cast members from the first film and new additions such as Jean-Claude Van Damme and Chuck Norris. That year, Stallone also co-wrote the book for the Broadway musical adaptation of Rocky.
2013: Starred in Escape Plan
In 2013, Stallone starred in the successful film "Escape Plan".
2013: Singing "The Star-Spangled Banner" in Grudge Match
In 2013, Sylvester Stallone last sang in a film, performing "The Star-Spangled Banner" with Robert De Niro in Grudge Match.
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" with Arnold Schwarzenegger, and the sports comedy drama "Grudge Match" with Robert De Niro. That year, Stallone was also 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, the third installment in the ensemble action film series, was released. This film was negatively received by critics and audiences and became the lowest-grossing film in the series.
2015: Returned to Rocky in Creed
In 2015, Stallone returned to the Rocky franchise with "Creed", earning widespread praise and his first Golden Globe Award.
2015: Reprising Rocky Balboa in Creed
In 2015, Sylvester Stallone reprised his role as Rocky Balboa in Creed, a spin-off sequel film focusing on Adonis "Donnie" Creed, the son of Apollo Creed. Stallone's performance garnered widespread acclaim, earning him a Golden Globe Award for Best Supporting Actor and an Academy Award nomination.
2017: Portrayed Stakar Ogord in Guardians of the Galaxy Vol. 2
In 2017, Stallone portrayed Stakar Ogord in the Marvel Cinematic Universe film "Guardians of the Galaxy Vol. 2".
2017: Guardians of the Galaxy Vol. 2 Appearance
In 2017, Sylvester Stallone appeared in Guardians of the Galaxy Vol. 2 as Stakar Ogord / Starhawk, the leader of a Ravagers faction.
March 2018: Formation of Balboa Productions
In March 2018, Sylvester Stallone formed a film studio named Balboa Productions with Braden Aftergood, signing a multi-year collaboration deal with Starlight Culture Entertainment.
March 2018: Creed II Production Begins
In March 2018, production began on Creed II, initially slated to be directed by Sylvester Stallone before Steven Caple Jr. was appointed.
May 2018: Rambo 5 Announced
In May 2018, a fifth installment in the Rambo franchise was announced.
August 2018: Adrian Grünberg Confirmed as Rambo: Last Blood Director
In August 2018, Adrian Grünberg was confirmed as the director of Rambo: Last Blood.
September 2018: Filming Begins for Rambo: Last Blood
By September 2018, filming for Rambo: Last Blood began, with Sylvester Stallone co-writing the script and reprising his role as John Rambo.
November 21, 2018: Creed II Released
On November 21, 2018, Creed II was released in the United States by Metro-Goldwyn-Mayer, receiving generally positive reviews and debuting to $35.3 million in its opening weekend, marking the biggest debut ever for a live-action release over Thanksgiving.
2018: Starred in Creed II
In 2018, Stallone starred in the sequel "Creed II", continuing his role as Rocky Balboa.
2018: Escape Plan Sequels and Creed II Script
In 2018, Sylvester Stallone co-starred in Escape Plan 2: Hades, released straight to home-video, and announced work on Escape Plan: The Extractors. In July 2018, he also finished a script for a Creed sequel featuring the return of Ivan Drago, and appeared in a documentary about director John G. Avildsen.
July 23, 2019: Rocky Sequel and Prequel Development
On July 23, 2019, Sylvester Stallone announced in an interview that a Rocky sequel and prequel were in development. The sequel plot involves Rocky befriending a young, undocumented immigrant fighter, while the prequel would be a television series following a young Rocky Balboa, but producer Irwin Winkler was hesitant about the series.
September 20, 2019: Rambo: Last Blood Released
On September 20, 2019, Rambo: Last Blood was released in the United States, grossing $18.9 million in its opening weekend.
2019: Rambo Film Release
In 2019, Stallone concluded his portrayal of John Rambo in the fifth Rambo film, continuing a role he began in 1982.
May 2020: Demolition Man Sequel Announced
In May 2020, Sylvester Stallone announced that a sequel to the 1993 film Demolition Man was in the works with Warner Brothers.
2020: Directing 40 Years of Rocky Documentary
In 2020, Sylvester Stallone hand-picked Derek Wayne Johnson to direct and produce a documentary on the making of the original Rocky, entitled 40 Years of Rocky, which features Stallone narrating behind-the-scenes footage from the making of the film.
2020: Voice Acting as Rambo in Mortal Kombat 11
In late 2020, Sylvester Stallone voiced the character Rambo in the fighting video game Mortal Kombat 11 as part of the game's 2nd Kombat Pack.
2021: Voicing King Shark in The Suicide Squad
In 2021, Sylvester Stallone voiced King Shark in the DC Extended Universe film The Suicide Squad.
November 2022: Tulsa King Streaming Television Debut
In November 2022, Sylvester Stallone made his streaming television debut in Tulsa King, a 9-episode series created by Taylor Sheridan and Terence Winter, which premiered on Paramount+.
2022: Starred in Tulsa King
In 2022, Stallone starred in the Paramount+ crime series "Tulsa King".
May 2023: The Family Stallone Premiere
In May 2023, Sylvester Stallone and his family starred in a reality television series called The Family Stallone, which was renewed for a second season seven days after its launch. Also in May 2023, Stallone reprised his role as Stakar Ogord in Guardians of the Galaxy Vol. 3.
October 2023: Expend4bles Release
In October 2023, Sylvester Stallone reprised his role as Barney Ross in Expend4bles, which became the lowest-grossing film in the franchise.
2023: Donation to Kyrsten Sinema's Campaign
In 2023, Stallone donated $11,600 to independent Senator Kyrsten Sinema's re-election campaign in Arizona and he and his family spent time with Pope Francis in a private meeting at the Vatican.
2023: Guardians of the Galaxy Vol. 3
In 2023, Sylvester Stallone reprised his role as Stakar Ogord in "Guardians of the Galaxy Vol. 3".
January 16, 2025: Appointment as Special Ambassador to Hollywood
On January 16, 2025, it was announced by Trump that Stallone would serve in a new role as a Special Ambassador to Hollywood, sharing the role with fellow actors Jon Voight and Mel Gibson. Trump stated that he wants these actors to make Hollywood "stronger than ever before" by bringing back business lost to "foreign countries".
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