- 2009: Starred in Judd Apatow's "Funny People" as seasoned comedian George Simmons who learns he has a terminal illness
- 2008: Starred in the family film "Bedtime Stories"
- 2008: Played a Mossad agent who becomes a hair stylist in "You Don't Mess with the Zohan"; also wrote and produced
- 2007: Co-starred with Kevin James in the comedy, "I Now Pronounce You Chuck and Larry"
- 2007: Starred as a 9/11 widower suffering from Post Traumatic Stress Disorder in Mike Binder's "Reign Over Me"
- 2006: Re-teamed with director Frank Coraci to star in the comedy "Click"
- 2005: Produced and starred as jailed ex-pro quarterback in the remake of the 1974 film "The Longest Yard"
- 2004: Co-starred with Téa Leoni and Paz Vega in the James L. Brooks comedy "Spanglish"
- 2004: Re-teamed with Drew Barrymore for the comedy "50 First Dates"; also executive produced
- 2003: Starred opposite Jack Nicholson in "Anger Management"
- 2002: First dramatic starring role, opposite Emily Watson in Paul Thomas Anderson's "Punch-Drunk Love"; received a Golden Globe nomination for Best Actor
- 2002: Wrote, produced and voiced many of the characters in the animated feature "Adam Sandler's 8 Crazy Nights."
- 2002: Starred opposite Winona Ryder in "Mr. Deeds," a loose reworking of "Mr. Deeds Goes to Town"
- 2001: Served as executive producer on the Rob Schneider vehicle "The Animal"
- 2000: Co-wrote, executive produced and played title role in "Little Nicky"
- 1999: Executive produced and made uncredited cameo in the Rob Schneider vehicle "Deuce Bigalow: Male Gigolo"
- 1999: Re-teamed with director Dugan for "Big Daddy"; also contributed to screenplay with Herlihy and produced
- 1998: First film to score big at the box-office, "The Waterboy"; co-written with Herlihy and directed by Coraci
- 1998: First appearance as a romantic lead, opposte Drew Barrymore in "The Wedding Singer"; written by Tim Herlihy and directed by former NYU undergraduate pal Frank Coraci
- 1996: Reteamed with Herlihy to write second starring vehicle, "Happy Gilmore"; directed by Dennis Dugan
- 1995: First starring role as "Billy Madison"; co-wrote with former NYU roommate and close friend Tim Herlihy
- 1995: "The Chanukah Song" (debuted on SNL) became surprise hit on the radio at holiday time
- 1994: Had supporting role in the feature film "Airheads"
- 1993: Released first comedy album, They're All Gonna Laugh at You!
- 1992: Feature film debut, "Shakes the Clown"
- 1990: Joined NBC's "Saturday Night Live" as a writer and occasional performer; became a featured player the following year
- 1987: Played recurring role of Theo's pal Smitty on NBC's "The Cosby Show"
- 1983: Debuted as a stand-up comic at Boston's Stitches Comedy Club at age 17
- 1972: Moved to Manchester, New Hampshire at age six
- Discovered by Dennis Miller while performing stand-up at The Improv in Los Angeles
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