He has also appeared twice on the original British edition of Whose Line Is It Anyway? In 1991, Wendt played the father in Michael Jackson's music video " Black or White".
In 1989, Wendt appeared as the eponymous protagonist in a BBC TV dramatization of Ivan Goncharov's novel Oblomov. Having grown up as a lifelong fan of his hometown Chicago White Sox and Chicago Bears, Wendt's Bob Swerski character is said to be a "spot-on" characterization of Chicago's south-side citizens. In the early 1990s, Wendt made cameo appearances on several episodes of SNL as Bob Swerski, one of the Chicago Superfans (along with cast members Chris Farley, Mike Myers, Robert Smigel, and one-time host, Joe Mantegna). In 1988 he played the part of "Witten" in the New Zealand-made film, Never Say Die. His first appearance on Saturday Night Live was in a season 11 (1985–1986) episode where he shared hosting duties with director Francis Ford Coppola. Wendt's handprints in cement, in front of Hollywood Hills Amphitheater at Walt Disney World's Disney's Hollywood Studios theme park.
Wendt appeared in the 1980 film My Bodyguard, and had small roles in the TV series Taxi, Soap, and M*A*S*H. Second City was also where he met his future wife, Bernadette Birkett, who played Cliff's Halloween date in the third season of Cheers and later in the series played the voice of Norm's never-seen wife, Vera. The woman working there handed him a broom and said "Welcome to the theater, kid" thus, his first job in show business was sweeping the floors. A viewing had inspired him to join and on his first day of employment, he showed up promptly at 11:30 am as he was instructed. Wendt is a 1975 alumnus of The Second City, which he discovered shortly after college. Wendt is an uncle of actor and former SNL writer and cast member Jason Sudeikis, his sister's son. He later attended the Jesuit Rockhurst College in Kansas City, Missouri, where he graduated with a B.A. He was expelled from the University of Notre Dame after he received a 0.00 GPA the first semester of his junior year.
He attended Campion High School in Prairie du Chien, Wisconsin. Wendt is of Irish and one quarter German descent.
His maternal grandfather was photographer Tom Howard. He is one of nine children, with six sisters-Nancy, Karen, Mary Ann, Kathryn, Loretta, and Marti-as well as two brothers, Tom and Paul. His parents were Loretta Mary ( née Howard) and George Robert Wendt, an officer in the Navy and a realtor. was born in the Beverly neighborhood on the south side of Chicago, Illinois.