- 2007: Directed Jack Nicholson and Morgan Freeman in "The Bucket List" as two terminally ill men who escape from a cancer ward and head off on a road trip with a wish list of tasks to accomplish before they die
- 2005: Stepped in to direct Jennifer Aniston and Kevin Costner in the comedy "Rumor Has It..."; replaced freshman director Ted Griffin who penned the script
- 2003: Directed and co-wrote the feature "Alex and Emma"; also played the character Wirtschafter
- 2001: Voice was used for a small part in "The Majestic"
- 1999: Appointed by California Governor Gray Davis to serve without salary as chairman of the nine-member state Children and Families First Commission
- 1999: Honored with a star on the Hollywood Walk of Fame (October 12); star is located next to his father's
- 1999: Made cameo appearance as himself in Albert Brooks' Hollywood comedy "The Muse"
- 1998: Acted in the political satire "Primary Colors" directed by Nichols and scripted by Elaine May
- 1996: Directed the civil rights drama "Ghosts of Mississippi"; co-star James Woods earned a Best Supporting Actor Academy Award nomination
- 1995: Reteamed with Sorkin, directing the romantic comedy "The American President"
- 1995: Played a radio shrink in "Bye, Bye Love"
- 1994: Acted in Woody Allen's "Bullets Over Broadway" and in Ephron's "Mixed Nuts"
- 1993: Played Tom Hanks' friend in Ephron's "Sleepless in Seattle"
- 1993: Castle Rock Entertainment (as well as New Line Cinema) purchased by the Turner Broadcasting System for $650 million
- 1992: Helmed the screen adaptation of Aaron Sorkin's Broadway play "A Few Good Men"; film received a Best Picture Oscar nomination
- 1991: Created (in collaboration with Phil Mishkin) and executive produced the short-lived CBS sitcom "Morton & Hayes"
- 1991: Acted in Nichols' "Regarding Henry"
- 1990: Acted with father in time-travel comedy "The Spirit of '76," directed by brother Lucas Reiner
- 1990: First feature collaboration with Mike Nichols, appearing in "Postcards From the Edge" as a movie producer
- 1990: Directed Kathy Bates in her Academy Award winning role, "Misery," an adaptation of a Stephen King novel
- 1989: Scored box office hit with the romantic comedy "When Harry Met Sally..." penned by Nora Ephron and co-starred Crystal
- 1987: First feature acting role in ten years, in Danny De Vito's directorial debut "Throw Momma From the Train," co-starring Crystal and De Vito
- 1987: Formed Castle Rock Entertainment (named for a fictional Maine town that appears in Stephen King's work) with partners Alan Horn, Glenn Padnick, Scheinman and Martin Shafer
- 1987: First film as producer, "The Princess Bride"; also directed; initial collaboration with William Goldman who adapted the film from his novel of the same name; Crystal appeared in a cameo
- 1986: Initial collaboration with producer Andrew Scheinman, "The Sure Thing"
- 1986: Helmed the coming-of-age tale "Stand By Me," adapted from a Stephen King novella
- 1984: First feature film as director and first screenplay credit, "This is Spinal Tap"; also wrote several songs and acted; first feature collaboration with Billy Crystal
- 1980: Broadway acting debut in his father's play "The Roast"
- 1978: First TV series as creator and executive producer (in collaboration with Mishkin), the short-lived sitcom "Free Country" (ABC); also wrote and starred as Lithuanian immigrant Joseph Bresner
- 1978: Executive produced and wrote (with Mishkin) first TV-movie, "More Than Friends" (ABC); also co-starred opposite Penny Marshall in the romantic comedy based on their own courtship
- 1974: First TV producing and directing credits, in collaboration with Phil Mishkin, on the CBS sitcom pilot "Sonny Boy"
- 1972: Wrote for the short-lived ABC sitcom "The Super"
- 1971: Debut as a regular on a TV series, as Michael Stivic (aka 'Meathead') on the ground-breaking sitcom "All in the Family" (CBS); also wrote occasionally; earned Golden Globe (1972, 1973, 1974, 1976, 1977) and Emmy (1972, 1973, 1975) nominations for Best Supporting Actor
- 1970: First major film role in the teen drama "Halls of Anger"
- 1970: TV acting debut in "The Partridge Family" (ABC)
- 1970: Reteamed with father for "Where's Poppa?"
- 1968: TV writing debut, the ABC special "Romp"
- 1966: First appearance in film, "Enter Laughing" directed by father Carl Reiner
- Worked in regional theater and with improvisational comedy troupes




