Silverman is known for his roles in the TV series Gimme A Break!, as well as in the films Brighton Beach Memoirs (1986) (a film version of the first play of Neil Simon’s Eugene Trilogy), Girls Just Want to Have Fun (1985), Caddyshack II (1988), Little Big League (1994), and Weekend at Bernie’s (1989).

Silverman played the title role in the television sitcom The Single Guy (which aired on NBC starting in 1995), as well as the lead role in the 1992 movie Little Sister. He has appeared on CSI: Miami (in a third-season episode called “Under the Influence”). He made a guest appearance on Friends in the episode “The One with the Birth.”

He appeared briefly on The Bold and the Beautiful in the early 2000s. He starred in the short-lived sitcom In Case of Emergency, which was a mid-season replacement on ABC for the 2006 season. He played the role of Eddie in Beethoven’s Big Break. He later guest starred in Psych in February 2009 and in Hot in Cleveland in 2012. He was in the movie Jam (2006). He appeared in the television show White Collar in the episode “Veiled Threat” as a con artist. He has also been in Inkubus and the upcoming Self Stored by Wood Haven Productions. He guest starred as a controversial standup comedian in Law & Order: Special Victims Unit in 2014.