History of Sylvester Stallone in Timeline
Sylvester Stallone is an acclaimed American actor and filmmaker with a career spanning over five decades. He has received numerous awards, including a Golden Globe and a Critics' Choice Award, and has been nominated for multiple Academy Awards and BAFTA Awards. Notably, he is one of only two actors to have starred in a number-one box-office film across six consecutive decades. His films have collectively grossed over $7.5 billion worldwide, solidifying his status as a major figure in the entertainment industry.
1 day ago : Stallone Protected Himself with Body Armor for Snipes' Intense 'Demolition Man' Performance.
Sylvester Stallone wore body armor to allow Wesley Snipes to deliver a convincing performance in 'Demolition Man'. Stallone praised Snipes' electrifying role and commitment to the film, highlighting their on-screen dynamic and friendship.
1919: Francesco "Frank" Stallone Sr.'s Birth
In 1919, Francesco "Frank" Stallone Sr., Sylvester Stallone's father, was born. He was a hairdresser who owned hair salons and was an avid polo player.
1921: Jacqueline "Jackie" Stallone's Birth
In 1921, Jacqueline "Jackie" Stallone (née Labofish), Sylvester Stallone's mother, was born. She was a celebrity astrologer and women's professional wrestling promoter.
July 6, 1946: Sylvester Stallone's Birth
On July 6, 1946, Sylvester Gardenzio Stallone, also known as "Sly", was born in the Hell's Kitchen neighborhood of Manhattan, New York City. He is the elder son of Jacqueline "Jackie" Stallone, a celebrity astrologer and women's wrestling promoter, and Francesco "Frank" Stallone Sr., a hairdresser.
1954: Mother opened Barbella's
In 1954, Sylvester Stallone's mother opened a women's gym called Barbella's in Washington, D.C.
September 1965: Attending American College of Switzerland
From September 1965 to June 1967, Sylvester Stallone attended the American College of Switzerland.
June 1967: End of studies at American College of Switzerland
Sylvester Stallone ended his studies at the American College of Switzerland in June 1967.
1968: Role in That Nice Boy
While attending the University of Miami, Stallone had a role in the drama That Nice Boy (aka The Square Root), filmed in 1968.
1969: Studying at the University of Miami
From 1967 to 1969, Stallone studied as a drama major at the University of Miami but did not graduate.
1969: Working with John Herzfeld on Horses
In 1969, Sylvester Stallone and John Herzfeld worked together on a low-budget self-produced film called "Horses".
1969: Moving to New York City
In 1969, Sylvester Stallone moved to New York City, struggling to find work as an actor.
1970: Stage Name Change
In 1970, Mike Stallone started using the stage name Sylvester E. Stallone.
1970: Starring Role in The Party at Kitty and Stud's
In 1970, Sylvester Stallone had his first starring role in the softcore pornography feature film The Party at Kitty and Stud's. He was paid US$200 for two days' work, which he did out of desperation after being evicted and becoming homeless.
1970: Minor Film Roles
In 1970, Sylvester Stallone had minor roles in M*A*S*H and Pigeons.
November 15, 1971: Score Stage Play Closing
On November 15, 1971, Sylvester Stallone's erotic off-Broadway stage play Score closed at the Martinique Theatre after 23 performances.
1971: Minor Film Roles
In 1971, Sylvester Stallone had minor roles in Bananas and Klute.
1972: Acting in a play and being cast in The Lords of Flatbush
In 1972, Sylvester Stallone was acting in a play that an agent attended and thought that Stallone fit the role of Stanley, a main character in The Lords of Flatbush.
1972: Low Point and Extra Role
In 1972, Sylvester Stallone was on the verge of giving up on his acting career. He failed to get a job as an extra in The Godfather and was relegated to a background role in What's Up, Doc?, starring Barbra Streisand.
1973: First Starring Role in No Place to Hide
Around mid-1973, Sylvester 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.
December 28, 1974: Marriage to Sasha Czack
On December 28, 1974, Sylvester Stallone married Sasha Czack.
1974: The Lords of Flatbush schedule
From 1972 to 1974 The Lords of Flatbush had a start-stop schedule over budget issues.
1974: Acting in The Lords of Flatbush
In 1974, Stallone found gradual work in films such as The Lords of Flatbush.
1974: Second Starring Role in The Lords of Flatbush
In 1974, Sylvester Stallone had his second starring role in The Lords of Flatbush.
1974: Release of the film Score
In 1974, the film Score, based on the stage play starring Sylvester Stallone, was released.
March 24, 1975: Inspiration for Rocky
On March 24, 1975, Sylvester Stallone saw the Muhammad Ali vs. Chuck Wepner fight, inspiring him to write the first draft of Rocky in three days.
1975: Supporting Roles in Films
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: "Gonna Fly Now" theme for Rocky
In 1976, Bill Conti recorded the famous "Gonna Fly Now" theme for Stallone's Academy Award-nominated film, Rocky, which was a U.S. No. 1 hit.
1976: Breakthrough with Rocky
In 1976, Stallone achieved critical and commercial success with his role as Rocky Balboa in the first film of the Rocky franchise, which he also wrote.
1976: Birth of Son Sage Moonblood Stallone
In 1976, Sylvester Stallone and Sasha Czack had their first son, Sage Moonblood Stallone.
1976: Release and Success of Rocky
In 1976, Sylvester Stallone gained worldwide fame with his starring role in the hit film Rocky, a sports drama about a struggling boxer taking on heavyweight champion Apollo Creed.
1977: Academy Award Nominations
In 1977, Sylvester Stallone became the third actor in history to be nominated for two Academy Awards for Best Original Screenplay and Best Actor for Rocky.
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 nominations for Sylvester Stallone. The film won the Academy Awards for Best Picture, Best Directing, and Best Film Editing.
1978: Directorial Debut with Paradise Alley
In 1978, Sylvester Stallone made his directorial debut and starred in the film Paradise Alley, a family drama about three brothers involved in professional wrestling. That same year, he also starred in F.I.S.T.
1978: Singing "Too Close to Paradise" for Paradise Alley
In 1978, Sylvester Stallone sang "Too Close to Paradise" for the movie "Paradise Alley", with music by Bill Conti.
1979: Birth of Son Seargeoh Stallone
In 1979, Sylvester Stallone and Sasha Czack had their second son, Seargeoh, who was later diagnosed with autism.
1979: Rocky II Success
In 1979, Sylvester Stallone wrote, directed, and starred in Rocky II. The sequel became a major success, grossing US$200 million.
1981: Falling Out with Joe Spinell
In 1981, Sylvester Stallone had a falling out with Joe Spinell during the shooting of "Nighthawks".
1981: Starring in Escape to Victory and Nighthawks
In 1981, Sylvester Stallone starred alongside Michael Caine and Pelé in Escape to Victory, and he also starred in the thriller Nighthawks.
1982: Portrayal of John Rambo in First Blood
In 1982, Sylvester Stallone portrayed the PTSD-plagued soldier John Rambo in First Blood, beginning his role across five Rambo films.
1982: Starred in "First Blood" and "Rocky III"
In 1982, Sylvester Stallone starred as John Rambo in "First Blood," an adaptation of David Morell's novel. He also wrote, directed, and starred in "Rocky III." Stallone underwent rigorous training to prepare for these roles, reducing his body fat percentage to 2.8% for "Rocky III".
1982: Singing "Take Me Back" in Rocky III
In 1982, Sylvester Stallone, as Rocky Balboa, sang "Take Me Back" to his on-screen wife, Adrian, in "Rocky III". The song was originally performed by his brother, Frank Stallone.
1983: Frank Stallone's Song "Far from Over" Success
In 1983, Frank Stallone's song "Far from Over", from the "Staying Alive" soundtrack, reached #10 on the U.S. hit charts.
1983: Directed "Staying Alive"
In 1983, Sylvester Stallone directed "Staying Alive", the sequel to "Saturday Night Fever", starring John Travolta. Although critically panned, the film was a commercial success.
1984: Hollywood Walk of Fame Star
In 1984, Stallone received a star on the Hollywood Walk of Fame.
1984: Starred 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 and performed a song for the soundtrack. Stallone turned down the lead male role in "Romancing the Stone" to make Rhinestone, a decision he later regretted.
February 14, 1985: Divorce from Sasha Czack
On February 14, 1985, Sylvester Stallone and Sasha Czack divorced.
December 15, 1985: Marriage to Brigitte Nielsen
On December 15, 1985, Sylvester Stallone married model and actress Brigitte Nielsen in Beverly Hills, California.
1985: Signed to remake "Angels with Dirty Faces"
Around 1985, Sylvester Stallone was signed to a remake of the 1939 James Cagney classic "Angels with Dirty Faces" as part of a multi-picture deal with Cannon Films. The remake was met with disapproval, and Cannon 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 with "Rocky IV" and "Rambo: First Blood Part II." He trained with Franco Columbu to develop his character's appearance for "Rocky IV". Both films were major financial successes.
1986: Released "Cobra" and formed White Eagle Enterprises
In 1986, Cannon opted to make the action film "Cobra" which was released and became a box-office success. It led to the setting up of his production company White Eagle Enterprises.
1986: Starring in Cobra
In 1986, Stallone starred in the action film Cobra.
1986: Alleged Sexual Assault in Las Vegas
In 1986, while filming a movie in Las Vegas, Stallone was accused of sexually assaulting a 16-year-old girl, who claimed he forced her into a threesome with his bodyguard. The incident led to a police report decades later.
1987: Consensual Relationship Claimed by Stallone's Attorneys
In 1987, Stallone's attorneys admitted that the actor had a consensual relationship with a woman who later accused him of sexual assault. Stallone's attorneys stated that they had two witnesses who refuted the claims.
1987: Initial Agreement with Toni-Ann Filiti
In 1987, Sylvester Stallone and his half-sister Toni-Ann Filiti reached an initial agreement regarding financial support.
1987: Starred 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 movie was poorly received by critics and was a box-office failure.
1988: Relationship with Jennifer Flavin Begins
In 1988, Sylvester Stallone began a relationship with model Jennifer Flavin.
1989: Acting in Tango and Cash
In 1989, Stallone starred in the action film Tango and Cash.
1989: Co-starred in "Tango & Cash"
In 1989, Sylvester Stallone co-starred alongside Kurt Russell in the buddy cop action film "Tango & Cash", which performed well both domestically and internationally.
1989: Death of Joe Spinell
In 1989, Sylvester Stallone's close friend, Joe Spinell, passed away.
1990: Release of 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: Starring in Oscar
In 1991, Stallone starred in the comedy Oscar, which failed at the box office.
1992: Starring in Stop! Or My Mom Will Shoot
In 1992, Stallone starred in the comedy Stop! Or My Mom Will Shoot, which had modest success.
1993: Starring in Cliffhanger and Demolition Man
In 1993, Stallone starred in the action films Cliffhanger and Demolition Man.
1993: Release of Demolition Man
In 1993, the movie "Demolition Man" was released.
February 1994: Birth of Janice Dickinson's Child and End of Engagement
In February 1994, Janice Dickinson gave birth to a child and Stallone ended his engagement with Dickinson after DNA tests confirmed he was not the father.
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.
1994: Acting in The Specialist
In 1994, Stallone starred in the action film The Specialist.
1995: Starred in "Judge Dredd"
In 1995, Sylvester Stallone played the title character in the science fiction action film "Judge Dredd". Although it was a domestic box-office disappointment, the film's overseas appeal saved it.
1995: Rekindled Relationship with Jennifer Flavin
In 1995, after a brief engagement with model Angie Everhart, Sylvester Stallone rekindled his relationship with Jennifer Flavin.
1996: Rediscovery of Faith
In 1996, Stallone rediscovered his Catholic faith after his daughter was born ill. This marked a return to the strict Catholic beliefs of his childhood.
1996: Starred in "Daylight"
In 1996, Sylvester Stallone starred in the disaster film "Daylight" as a disgraced former emergency services chief. "Daylight" underperformed at the domestic box office but did better overseas.
May 1997: Marriage to Jennifer Flavin
In May 1997, Sylvester Stallone married Jennifer Flavin.
1997: Starring in Cop Land
In 1997, Stallone starred in the drama Cop Land, gaining weight for his role as a powerless sheriff.
1998: Voice-over work for "Antz"
In 1998, Sylvester Stallone did voice-over work for the animated film "Antz", which was a success domestically.
1998: Receiving a BFA Degree
In 1998, Sylvester Stallone was granted a Bachelor of Fine Arts (BFA) degree by the University of Miami after requesting that his acting and life experiences be accepted in exchange for his remaining needed college credits.
February 26, 2000: Alleged Incident with Margie Carr
On February 26, 2000, an alleged incident involving Sylvester Stallone and Margie Carr occurred at a Santa Monica fitness center.
2000: Starred in "Get Carter"
In 2000, Sylvester Stallone starred in the thriller "Get Carter", a remake of the 1971 British film of the same name, but it was poorly received.
February 2001: Rape Lawsuit Filed by Margie Carr
In February 2001, Margie Carr filed a lawsuit against Sylvester Stallone, accusing him of rape.
2001: Starred in "Driven"
In 2001, Sylvester Stallone starred in the film "Driven", which was a critical and commercial failure.
2002: Starred in "Avenging Angelo" and "D-Tox"
In 2002, Sylvester Stallone starred in "Avenging Angelo" and "D-Tox", which were critical and commercial failures.
2003: Played a villain in "Spy Kids 3-D: Game Over" and cameo in "Taxi 3"
In 2003, Sylvester Stallone played a villainous role in "Spy Kids 3-D: Game Over", which was a box-office success, and had a cameo appearance in the French film "Taxi 3".
2005: Co-presented "The Contender", guest appearance in "Las Vegas", inducted Hulk Hogan into WWE Hall of Fame, released "Sly Moves"
In 2005, Sylvester Stallone co-presented "The Contender" and made a guest appearance in "Las Vegas". He inducted Hulk Hogan into the WWE Hall of Fame and released his book "Sly Moves".
2006: Return to Rocky with Rocky Balboa
In 2006, Stallone reprised his role as Rocky Balboa in the film Rocky Balboa.
2006: Return to Strict Catholicism and 700 Club Interview
In 2006, Stallone returned to being a strict Catholic and was interviewed by Pat Robertson on the Christian Broadcasting Network's 700 Club, where he discussed "losing his way" in Hollywood and putting things "in God's hands".
2006: Expressed desire to direct film about Musa Dagh
In 2006, Sylvester Stallone expressed his desire to direct a film about Musa Dagh, adapted from Franz Werfel's novel "The Forty Days of Musa Dagh," detailing the genocide of the Armenian community in 1915.
2006: Comeback with "Rocky Balboa" and discussed "Death Wish" remake
In 2006, Sylvester Stallone had a comeback with "Rocky Balboa", which he wrote, directed, and starred in. The film was a critical and commercial hit. That year, he also discussed directing and starring in a remake of "Death Wish", but he later told the publication that he was no longer involved.
2007: Possession of Human Growth Hormone
In 2007, customs officials in Australia discovered 48 vials of the synthetic human growth hormone Jintropin in Sylvester Stallone's luggage, leading to a court hearing.
January 25, 2008: Rambo released in theaters
On January 25, 2008, Sylvester Stallone reprised his role in "Rambo", the fourth installment of the franchise. The film opened in 2,751 theaters and grossed US$6,490,000 on its opening day.
February 2008: Rocky or Rambo?
In February 2008, Sylvester Stallone stated that Rocky is his 'first baby'. He also stated that Rocky could be interpreted as the 'conscious' and Rambo as the 'unconscious' of the same character.
2008: Endorsement of John McCain for President
In 2008, Stallone endorsed John McCain for that year's presidential election.
July 2009: Cameo in "Kambakkht Ishq"
In July 2009, Sylvester Stallone made a cameo appearance in the Bollywood film "Kambakkht Ishq", where he played himself.
August 13, 2010: The Expendables was released
On August 13, 2010, Sylvester Stallone's film "The Expendables" was released. The film took US$34,825,135 in its opening weekend, going straight in at No. 1 in the US box office. The figure marked the biggest opening weekend in Stallone's career.
December 7, 2010: Voted into the International Boxing Hall of Fame
On December 7, 2010, it was announced that Sylvester Stallone was voted into the International Boxing Hall of Fame in the non-participant category.
2010: Launch of The Expendables Franchise
In 2010, Stallone launched The Expendables film franchise, starring as Barney Ross.
2010: GQ Magazine Interview on Spirituality
In 2010, Stallone told GQ magazine that he considers himself spiritual and believes in the spirit of man, while not belonging to a structured church, expressing appreciation for some aspects of Catholicism while also acknowledging the agony it has caused.
2011: Death of Frank Stallone Sr.
In 2011, Francesco "Frank" Stallone Sr., Sylvester Stallone's father, passed away.
2011: Provided voice for a lion in Zookeeper
In 2011, Sylvester Stallone provided the voice of a lion in Kevin James' comedy "Zookeeper".
August 17, 2012: The Expendables 2 was released
On August 17, 2012, "The Expendables 2" was released and received a positive critical reception of 67% on Rotten Tomatoes.
August 26, 2012: Death of Half-Sister Toni Ann Filiti
On August 26, 2012, Sylvester Stallone's half-sister, Toni Ann Filiti, died of lung cancer at the age of 48.
2012: Half-Sister Toni-Ann Filiti Death
In 2012, Half-Sister Toni-Ann Filiti, died before Stallone's settlement became public.
2012: Death of Son Sage Moonblood Stallone
In 2012, Sylvester Stallone's son, Sage Moonblood Stallone, died of heart disease at the age of 36.
2013: Starring in Escape Plan
In 2013, Stallone starred in the successful film Escape Plan and appeared in its sequels.
2013: Performing "The Star-Spangled Banner" in Grudge Match
In 2013, Sylvester Stallone and Robert De Niro performed "The Star-Spangled Banner" together in the film "Grudge Match".
2013: Stallone's Action Films and Writing Credit
In 2013, Sylvester Stallone starred in "Bullet to the Head" and "Escape Plan", alongside Arnold Schwarzenegger. He also appeared in "Grudge Match" with Robert De Niro. Stallone was credited as the writer for the Jason Statham action film "Homefront".
2013: Settlement with Half-Sister Toni-Ann Filiti
In 2013, it was reported that Sylvester Stallone paid a $2 million settlement and a trust for medical expenses to his half-sister Toni-Ann Filiti after she threatened to accuse him of abuse.
August 15, 2014: Release of The Expendables 3
On August 15, 2014, "The Expendables 3", the third installment in the series, was released. Despite the ensemble cast including Wesley Snipes, Antonio Banderas, Mel Gibson and Harrison Ford, the film was negatively received and became the lowest-grossing film in the series.
2015: Hindu Ritual for Son Sage
In 2015, Stallone performed a Hindu Tithi Shradh ritual at Haridwar for his son Sage, upon the advice of a Vedic scholar.
2015: Return to Rocky with Creed
In 2015, Stallone returned to the Rocky series with Creed, mentoring Apollo Creed's son. He received widespread praise and his first Golden Globe Award, as well as a third Academy Award nomination.
2015: Stallone's role as Rocky Balboa in Creed
In 2015, Sylvester Stallone reprised his role as Rocky Balboa in "Creed", a spin-off-sequel film. The film received critical acclaim, and Stallone won the Golden Globe Award for Best Supporting Actor and received his third Academy Award nomination.
2016: Comments on Donald Trump and Rejection of NEA Chair Offer
In 2016, Stallone described Donald Trump as a "Dickensian character" and "larger than life" but did not endorse him in the Republican primaries. He also declined an offer to become Chair of the National Endowment for the Arts, citing a desire to work on veterans' issues.
2016: Report of Sexual Assault Allegation Published
In 2016, the Las Vegas Metropolitan Police Department published a report alleging that Stallone was accused of sexually assaulting a 16-year-old girl in 1986. The teen claimed that Stallone forced her into a threesome with his bodyguard. Stallone's representative denied the allegation and his ex-wife, Brigitte Nielsen, defended him, stating that she was with him at the time of the alleged assault.
November 2017: Woman Accuses Stallone of Sexual Assault
In November 2017, a woman accused Stallone of sexually assaulting her at his Santa Monica office in the early 1990s. Stallone denied the claim, and his attorney stated the accuser filed a report after an entertainment website declined to publish the story.
2017: Appearance 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: Balboa Productions Formation
In March 2018, Sylvester Stallone formed Balboa Productions with Braden Aftergood, serving as co-producer for their film and television projects. The studio signed a multi-year collaboration deal with Starlight Culture Entertainment.
March 2018: Creed II Production Begins
In March 2018, production began on "Creed II". Stallone was originally slated to direct, but Steven Caple Jr. was appointed instead.
May 2018: Rambo 5 Announcement
In May 2018, a fifth installment in the Rambo franchise was announced.
June 2018: Los Angeles District Attorney's Office Opens Investigation
In June 2018, the Los Angeles District Attorney's office confirmed that the Santa Monica Police Department had presented a sex crimes case against Stallone to a special prosecution task force for review, following the sexual assault accusation.
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: Rambo: Last Blood Filming Begins
By September 2018, filming for "Rambo: Last Blood" had begun. Stallone co-wrote the script and reprised his role as John Rambo.
October 2018: Los Angeles District Attorney's Office Declines to Charge Stallone
In October 2018, the Los Angeles District Attorney's office decided not to charge Stallone for the alleged assault, citing a lack of corroborating witnesses. Stallone, in turn, filed a police report regarding the accuser lying on an official document.
November 21, 2018: Creed II Release and Reception
On November 21, 2018, "Creed II" was released in the United States by Metro-Goldwyn-Mayer. The film received generally positive reviews and had a successful opening weekend, grossing $35.3 million.
2018: Starring in Creed II
In 2018, Stallone starred in the sequel Creed II.
2018: Escape Plan 2: Hades and Creed II Script
In 2018, Sylvester Stallone co-starred in "Escape Plan 2: Hades" with Dave Bautista. He also announced he had finished a script for a sequel to "Creed", including the return of Ivan Drago. Stallone was also featured in the documentary "John G. Avildsen: King of the Underdogs".
July 23, 2019: Rocky Sequel and Prequel Development
On July 23, 2019, Stallone mentioned in an interview with Variety that a new Rocky sequel and a prequel television series are in development. The potential plot of the sequel would involve Rocky befriending a young undocumented immigrant. Discussions for the prequel television series were underway, focusing on a young Rocky Balboa.
September 20, 2019: Rambo: Last Blood Release
On September 20, 2019, "Rambo: Last Blood" was released in the United States, grossing $18.9 million in its opening weekend and ultimately grossing $91 million worldwide.
2019: Rambo Film Series Conclusion
In 2019, Stallone concluded his portrayal of John Rambo across five Rambo films (1982–2019).
May 2020: Demolition Man Sequel Announcement
In May 2020, Sylvester Stallone announced that a sequel to the 1993 film "Demolition Man" is in the works with Warner Brothers.
2020: 40 Years of Rocky Documentary
In 2020, Derek Wayne Johnson directed and produced a documentary on the making of the original Rocky, titled "40 Years of Rocky", featuring Stallone narrating behind-the-scenes footage.
2020: Death of Jackie Stallone
In 2020, Jacqueline "Jackie" Stallone, Sylvester Stallone's mother, passed away.
2020: Rambo in Mortal Kombat 11
In late 2020, Sylvester Stallone voiced Rambo in the fighting video game "Mortal Kombat 11", as part of the game's 2nd Kombat Pack.
2021: Voice of King Shark in The Suicide Squad
In 2021, Sylvester Stallone voiced King Shark in the DC Extended Universe film "The Suicide Squad".
August 19, 2022: Jennifer Flavin Files for Divorce
On August 19, 2022, Jennifer Flavin filed for divorce from Sylvester Stallone after 25 years of marriage.
September 23, 2022: Reconciliation with Jennifer Flavin
On September 23, 2022, Sylvester Stallone and Jennifer Flavin reconciled.
November 2022: Streaming Television Debut in Tulsa King
In November 2022, Sylvester Stallone made his streaming television debut in "Tulsa King" on Paramount+, playing a Mafia boss. The series was created by Taylor Sheridan and Terence Winter.
2022: Starring in Tulsa King
In 2022, Stallone starred in the Paramount+ crime series Tulsa King.
May 2023: The Family Stallone and Guardians of the Galaxy Vol. 3
In May 2023, Sylvester Stallone and his family starred in the reality television series "The Family Stallone", which was renewed for a second season shortly after its launch. Stallone also 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 was a critical and commercial failure, becoming the lowest-grossing film in the franchise.
2023: Donation to Kyrsten Sinema's Campaign and Meeting with Pope Francis
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 in a private meeting at the Vatican.
2023: Appearance in Guardians of the Galaxy Vol. 3
In 2023, Stallone portrayed Stakar Ogord in the Marvel Cinematic Universe film Guardians of the Galaxy Vol. 3.
2024: Attendance at Mar-a-Lago and Praise for Donald Trump
In 2024, after Donald Trump's 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, Stallone was announced by Trump to serve as a Special Ambassador to Hollywood, alongside Jon Voight and Mel Gibson, aiming to strengthen Hollywood by bringing back business lost to foreign countries.
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