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Willard achieved wider fame as Martin Mull's sidekick, " Jerry Hubbard ," on the television shows Fernwood 2 Night, Forever Fernwood, and America 2-Night, which parodied the nighttime talk shows of the day.

He was an original cast member of the NBC comedy series Real People in 1979 and again from 1981-1983.

He plays Tom Osbourne in the 1987 Academy Award winning short film, Ray ’ s Male Heterosexual Dance Hall.

From 1987 to 1989, he starred as a bartender / straightman in Sid and Marty Krofft's D. C. Follies, and was host to the Krofft puppets portraying political figures of the time.

In 1990, Willard hosted the cable TV show " Access America " on the Ha!

Comedy Network.

As part of that show, he appeared September 21, 1990 on Episode # 7 of the cult Public-access television show Decoupage with Summer Caprice.

In 1995, Willard reunited with his Fernwood co-star playing Scott, the romantic partner of Mull's character Leon Carp, on Roseanne.

The couple married in the episode " December Bride ," and Scott became a recurring character during the series ' final two seasons.

That same year, Willard had guest-starred in three episodes of Sister, Sister, starring Tia and Tamera Mowry ; Willard played Carl Mitushka, a teacher at Roosevelt High who often spoke popular teenage slang terms in order to sound cool to his students.

Willard guest-voiced a 1999 episode of The Simpsons titled Sunday, Cruddy Sunday as Wally Kogen, a travel agent.

From 2001 to 2002, he played the father of five children on Maybe It's Me.

He has also guest-starred in an episode of The Weird Al Show.

He and Mull joined up again for The History Of White People in America.

He played Mayor Deebs in Roxanne starring Steve Martin.

His “ I would rather be with the people of this town than with the finest people in the world .” has been widely quoted.