Debuted as a stand-up comic at Boston's Stitches Comedy Club at age 17
Played recurring role of Theo's pal Smitty on NBC's "The Cosby Show"
Discovered by Dennis Miller while performing stand-up at The Improv in Los Angeles
Feature film debut, "Shakes the Clown"
Released first comedy album <i>They're All Gonna Laugh at You!</i>
Landed supporting role in the feature film "Airheads"
"The Chanukah Song" (debuted on "SNL") became surprise hit on the radio at holiday time
Reteamed with Herlihy to write second starring vehicle "Happy Gilmore"; first collaboration with director Dennis Dugan
Re-teamed with director Dugan for "Big Daddy"; also contributed to screenplay with Herlihy and produced
Executive produced and made uncredited cameo in the Rob Schneider vehicle "Deuce Bigalow: Male Gigolo"
Co-wrote, executive produced and played title role in "Little Nicky"
Served as executive producer on the Rob Schneider vehicle "The Animal"
Starred opposite Winona Ryder in "Mr. Deeds," a loose reworking of "Mr. Deeds Goes to Town"
Wrote, produced and voiced many of the characters in the animated feature "Adam Sandler's 8 Crazy Nights."
Starred opposite Jack Nicholson in "Anger Management"
Re-teamed with Drew Barrymore for the comedy "50 First Dates"; also executive produced
Co-starred with Téa Leoni and Paz Vega in the James L. Brooks comedy "Spanglish"
Produced and starred as jailed ex-pro quarterback in the remake of the 1974 film "The Longest Yard"
Re-teamed with director Frank Coraci to star in the comedy "Click"
Starred as a 9/11 widower suffering from Post Traumatic Stress Disorder in Mike Binder's "Reign Over Me"
Co-starred with Kevin James in the comedy "I Now Pronounce You Chuck & Larry"
Played a Mossad agent who becomes a hair stylist in "You Don't Mess with the Zohan"; also wrote and produced
Starred in the family film "Bedtime Stories"
Co-starred with Jennifer Aniston in the romantic comedy "Just Go With It"
Played dual starring roles in the family comedy "Jack and Jill"; seventh film collaboration with director Dennis Dugan
Co-starred with fellow "Saturday Night Live" (NBC) alum Andy Samberg as father and son in "That's My Boy"
Starred in his first sequel, "Grown Ups 2"
Reteamed with Drew Barrymore in romantic comedy "Blended."
Starred in Chris Columbus-directed comedy adventure "Pixels."
Starred in first film for Netflix, controversial western comedy "The Ridiculous 6"