- 2008: Reprised (also wrote and directed) the role of war hero John Rambo for the fourth time in "Rambo"
- 2006: Starred (also directed and wrote) in the critical and commercial hit, "Rocky Balboa"; the sixth and final installment of his successful Rocky series
- 2005: Co-presenter alongside Sugar Ray Leonard of the NBC Reality boxing series "The Contender"
- 2004: Lent his name and image to the start-up publication Sly; focusing on health and fitness
- 2003: Played a villainous role in the third installment of the Spy Kids trilogy "Spy Kids 3-D: Game Over"
- 2001: Teamed onscreen with Burt Reynolds in "Driven"; Stallone reportedly contributed to the screenplay
- 2000: Had title role in the remake of "Get Carter"
- 1998: Provided the voice for Weaver, the soldier ant buddy of Woody Allen's in the animated feature "Antz"
- 1997: Delivered a change of pace turn as a partially deaf New Jersey sheriff in "Cop Land"
- 1995: Starred in the title role of the sci-fi actioner "Judge Dredd"
- 1995: Reportedly agreed to a multi-picture deal with Universal Pictures that would pay at least $60 million for three films
- 1993: First film (also rewrote script) with Renny Harlin, "Cliffhanger"
- 1991: Opened Planet Hollywood Restaurant in New York; co-owned with Arnold Schwarzenegger and Bruce Willis
- 1990: Re-teamed (starred and scripted) with original director John G. Avildsen for the fifth installment, "Rocky V"
- 1988: Again reprised other signature role (also scripted) in "Rambo III"
- 1985: Starred (also wrote and directed) in "Rocky IV"
- 1985: First executive producer credit for TV-movie, "Heart of a Champion: The Ray Mancini Story"
- 1984: Starred opposite Dolly Parton in "Rhinestone"
- 1983: First feature as a producer, "Staying Alive"; also directed and contributed to screenplay
- 1982: Reprised signature role (also scripted and directed) in "Rocky III"
- 1982: First played character of John Rambo in "First Blood"
- 1981: Co-starred in the John Huston-directed "Escape to Victory"
- 1979: Reprised role (also wrote and directed) for "Rocky II"
- 1978: Directorial debut (also scripted), "Paradise Alley"; later turned screenplay into a novel
- 1976: Screenwriting debut (also starred), "Rocky"; earned Oscar nominations as Best Actor and for Best Original Screenplay
- 1974: First starring role in the cult hit, "The Lords of Flatbush"
- 1974: Moved to Los Angeles
- 1973: First major role in "Rebel"
- 1971: Entered mainstream film with an uncredited appearance as a mugger in Woody Allen's "Bananas"
- 1970: First film appearance, a soft-core porn, "Party at Kitty and Stud's"
- 1969: Enrolled in University of Miami; dropped out two years later to pursue acting career
- 1967: Returned to the United States
- 1961: Moved to Philadelphia with mother and stepfather
- Worked as usher at Walter Reade Theater in NYC while writing screenplays; also swept out Bronx Zoo lion cages
- Moved to New York City
- Wrote a biographical drama about Edgar Allen Poe; many claim it is one of the great unproduced scripts in Hollywood
- Penned early drafts of what would become "Rocky"
- Family settled in Maryland
- Taught children of career diplomats and young royalty at American College of Switzerland




