Levy originally met future TV collaborators Dave Thomas and Martin Short while attending McMaster University in Hamilton, Ontario as well as filmmaker Ivan Reitman and magician Doug Henning. He made his feature debut starring opposite Andrea Martin in "Cannibal Girls" (made around 1970, released 1973), an uneven horror-comedy from future "billion dollar director" Reitman. Levy was also featured in the cast of the legendary Toronto production of "Godspell" (1972-73) along with Short, Thomas, Martin, Gilda Radner and Paul Shaffer. After spending two years performing with Toronto's Second City troupe, Levy moved to Pasadena California with John Candy and Joe Flaherty to start a new company, but the venture failed. They got involved with the original version of "Second City TV"—a locally produced show for Toronto TV.

Levy made his TV producing debut as executive producer, co-writer and performer of "The Last Polka" (HBO, 1985), a mock documentary on Josh and Stan Schmenge, a fictional polka band featured in numerous "SCTV" sketches. He made his TV directing debut (while also executive producing, writing and starring) with another enlarged skit, "Autobiographies: The Enigma of Bobby Bittman" (Cinemax, 1988). Levy helmed a cable special for Martin Short, "I, Martin Short, Goes Hollywood" (HBO, 1989), and did the same for the premiere episode of "The Martin Short Show" (NBC, 1994). In features Levy had character roles in a number of 80s comedies including Second City alum Harold Ramis' "National Lampoon's Vacation" (1983) and "Club Paradise" (1986), and alongside John Candy in "Splash" (1984) and "Armed and Dangerous" (1986). His 90s feature credits include "Stay Tuned" (1992), "I Love Trouble" (1994), and as Steve Martin's incomprehensible neighbor in "Father of the Bride Part II" (1995).

The hilariously straight-faced send-up of small-town show-biz aspirations "Waiting for Guffman" (1997) marked a Renaissance for Levy's career and the first of several collaborations with writer-director-performer Christopher Guest. The comic routinely threatens to steal the movie (even from brilliant performers like Guest, Fred Willard and Catherine O'Hara) as a dentist who spouts passé Johnny Carson-isms who, tapped to star in a small town stage show, soon dreams of a life in the limelight. Further bolstering Levy's street cred with young audiences was his role as Jason Biggs' square but loving and emotionally available father (aka Jim's Dad) in the huge hit comedy "American Pie" (1999), a role he reprised for the sequels "American Pie 2" (2001) and "American Wedding" (2003).

In 2000, with his career in a fresh new cycle. Levy again collaborated with Guest on the script for the mockumentary about dog breeders "Best in Show.” The hilarious film--which like most of Guest's works was also highly improvised by the actors--was a critical hit and Levy's portrayal of Gerald 'Gerry' Fleck, a man with (literally) two left feet, was one of the movie's highlights. He was tapped by "American Pie" scribes Paul and Chris Weitz to co-star opposite Chris Rock in their "Here Comes Mr. Jordan/Heaven Can Wait" remake "Down to Earth" (2001), had a key role as a slick Bloomingdale's salesman in the John Cusack-Kate Beckinsale romantic fable "Serendipity" (2001) and took the role of TV kids show director Gil Bender, one of the few humans populating the behind-the-scenes world of the puppet (or " fabricated American") Fox comedy series "Greg the Bunny" (2002), a short-lived cult classic in some circles.

Levy had yet another watershed year in 2003 with his hysterically low-key and fully-fleshed character Mitch Cohen, a tuned-in, dropped-out folk singer gingerly tiptoeing toward mental health and a career comeback in Guest's outrageous "A Mighty Wind," which Levy also co-wrote. He also had all of the best one-liners ("You got me straight trippin', Boo") as the seemingly white and uptight pal of Steve Martin's who develops a lusty crush on ex-con Queen Latifah in the amusing hit comedy "Bringing Down the House." He also had a small role as the high school principal in "Dumb and Dumberer: When Harry Met Lloyd" before reprising his most iconic part, Jim's Dad, for "American Wedding." He next brought a much-needed comic verve (but not enough to redeem the film, or his decision to appear in it) to his role as an overzealous truant officer in the Mary-Kate and Ashley Olsen feature film "New York Minute" (2004).

Levy's next vehicle was the hackneyed, derivative action-buddy flick "The Man" (2005), which attempted to drive laughs by pairing Samuel L. Jackson's hard-edged cop with Levy's awkward dentist who's drawn into a crime scheme. Levy then joined the original cast for the sequel “Cheaper By the Dozen 2” (2005), playing the head of a large, over-achieving family and long-time rival of Tom Baker (Steve Martin). Meanwhile, Levy spent 2005 working on several projects: “For Your Consideration” (2006), a parody about three actors whose small indie feature suddenly gets award buzz; “Curious George” (2006), the animated adventure of an inquisitive little monkey; and “Over the Hedge” (2006), based on the United Media Syndicate comic strip about a mischievous con-artist raccoon (Bruce Willis) and his sensitive turtle pal (Garry Shandling).