Tall and lanky, with curly brown hair and features that made him perfectly cast as an average Joe, Stern was born and raised in Bethesda, Maryland. Completing high school at age 17, he immediately headed for NYC where he briefly studied at HB Studios before landing a series of stage roles. Spotted by a casting agent, Stern landed the memorable supporting role of Cyril, who fails to land a basketball scholarship, in "Breaking Away". The actor went on to appear in support of Jill Clayburgh in three movies ("Starting Over" 1979; "It's My Turn" 1980; and "I'm Dancing as Fast as I Can" 1982) and appeared in two Woody Allen films ("Stardust Memories" 1980 and "Hannah and Her Sisters" 1986). Although Stern worked continuously, he really didn't hit his stride until the 1990s with the back-to-back hits "Home Alone" and "City Slickers" (1991). In the former, he was partnered with Joe Pesci as a pair of inept burglars while the latter saw him play Billy Crystal's pal, the perpetually depressed Phil. Capitalizing on those successes, Stern recreated the roles in the inevitable sequels.
Branching out, Stern stepped behind the cameras to make his feature directorial debut with "Rookie of the Year" (1993), an amiable kidflick in which he played the a slow-witted pitching coach. He went on to executive produce and star in the lackluster comedy "Bushwhacked" (1995) before teaming with Dan Aykroyd and Damon Wayans in "Celtic Pride" (1996), about two fans who kidnap a rival basketball star to try to ensure victory for their team. Actor-turned-helmer Peter Berg elicited a nice turn from Stern as an upstanding family man who becomes embroiled in an accidental killing in the black comedy "Very Bad Things" (1998).
Returning to the small screen, Stern provided the voice for the title character of "Dilbert" in the UPN animated series that aired from 1999 to 2000. The actor encountered a bit of negative publicity when he was sued by CBS when he withdrew from the lead role in the unaired sitcom "Partners" in 1999. He countersued claiming breach of contract and the matter was settled out of court. Clearly there were no hard feelings as he debuted on the network in the fall of 2001 in "Danny", a sitcom he also co-created, wrote and executive produced about a newly divorced man coping with his job at a recreation center, the difficulties of being a single parent and the trauma of entering his forties. Although the series showed promise, it failed to deliver big ratings and suffered the dubious distinction of being the first series cancelled in the 2001-02 season. A follow-up series, "Regular Joe" (ABC, 2003), about an empty-nester widower who's life is changed when his daughter returns home with a baby, was also short-lived. Stern then received good notices for the play "Barbra's Wedding," which he wrote and starred in during its 2005 debut, playing a washed up but egotistical B-list actor struggling to keep afloat who becomes indignant when he's not invited to neighbor Barbra Streisand's wedding.