He also became known for co-writing and appearances in a string of films with Christopher Guest, including Waiting for Guffman (1996), Best in Show (2000), A Mighty Wind (2003), and For Your Consideration (2006).

From 2015 to 2020, he starred as Johnny Rose in the sitcom Schitt's Creek, a comedy series that he co-created with his son and co-star Dan Levy.

[11] The 1972–1973 Toronto production of the hit musical Godspell opened at the Royal Alexandra Theatre and was intended to be a run of a few dozen performances for a subscription audience.

After an enthusiastic response from the audience, the scheduled run at the Royal Alexandra ended and the show moved uptown to the Bayview Playhouse in Leaside.

Celebrities impersonated by Levy on SCTV include Perry Como, Ricardo Montalbán, Alex Trebek, Gino Vannelli, Sean Connery, Howard Cosell, Henry Kissinger, Menachem Begin, Bud Abbott, Milton Berle, John Charles Daly, Gene Shalit, Judd Hirsch, Jack Carter, Muammar al-Gaddafi, Tony Dow, James Caan, Lorne Greene, Rex Reed, Ralph Young (of Sandler and Young), F. Lee Bailey, Ernest Borgnine, former Ontario chief coroner and talk show host Dr. Morton Shulman, Norman Mailer, Neil Sedaka and Howard McNear as Floyd the Barber.

Original Levy characterizations on SCTV are news reporter Earl Camembert, comic Bobby Bittman, scandal sheet entrepreneur Dr. Raoul Withers, "report on business" naïf Brian Johns, 3-D horror auteur Woody Tobias Jr., cheerful Leutonian accordionist Stan Schmenge, lecherous dream interpreter Raoul Wilson, hammer-voiced sports broadcaster Lou Jaffe, diminutive union patriarch Sid Dithers ("San Francisckie!

"), fey current-events commentator Joel Weiss, buttoned-down panel show moderator Dougal Currie, smarmy Just for Fun emcee Stan Kanter, energetic used car salesman Al Peck, guileless security guard Gus Gustofferson, Phil the Garment King (also of Phil's Nails), and the inept teen dance show host Rockin' Mel Slirrup.

He is the co-writer and frequent cast member of Christopher Guest's mockumentary features, particularly A Mighty Wind (2003), where his sympathetic performance as emotionally unstable folksinger Mitch Cohen won kudos; his accolades included a Satellite Award for Best Supporting Actor – Musical or Comedy and the prestigious New York Film Critics Circle Award for Best Supporting Actor.

From the 1980s through the 2010s, Levy appeared in National Lampoon's Vacation (1983), Splash (1984), Club Paradise (1986), Father of the Bride (1991), Father of the Bride Part II (1995), Stay Tuned (1996), Multiplicity (1996), the American Pie film series (1999–2012), Serendipity (2001), Bringing Down the House (2003), Cheaper by the Dozen 2 (2005), Madea's Witness Protection (2012), and other comedies.

This makes him one of only four two-time honourees, alongside fellow SCTV alumni John Candy, Martin Short, and Catherine O'Hara.

[28] In 2011, Levy was made a Member of the Order of Canada "for his contributions as a comic actor and writer, and for his dedication to charitable causes" and promoted to the rank of Companion in 2022.

[29][30] On May 22, 2012, Levy delivered a commencement address at Dalhousie University, in Halifax, Nova Scotia, and was awarded the degree Doctor of Laws (honoris causa).

On June 11, 2012, Levy was presented with the Queen Elizabeth II Diamond Jubilee Medal by the lieutenant governor of Ontario.