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Herman had appeared in the films Born on the Fourth of July, Lost Angels, and Let It Be Me.^[2]

Herman was part of the cast of John Leguizamo's short-lived series House of Buggin' in 1995. When Fox canceled the series to replace it with a sketch comedy show, Herman signed on as one of nine original cast members of MADtv when the series began in 1995.^[3]

Herman's MADtv characters included Mike Lawson (Incredible Findings), Generation X anchorman Marsh (X News), and concerned father Joel Linder.

Herman lampooned celebrities and famous figures such as Don Adams (as Maxwell Smart from Get Smart), Tim Allen (as Tim Taylor from Home Improvement), Woody Allen, Nicolas Cage, Bill Clinton, Bob Dole, David Duchovny (as Fox Mulder from The X-Files), Larry Flynt, Tom Hanks (as Forrest Gump and as Jim Lovell from Apollo 13), Larry King, Kenny Kingston, Regis Philbin, Charles Nelson Reilly, John Ritter (as himself and as Jack Tripper from Three's Company), Joel Schumacher, Robert Shapiro, Pauly Shore, Brent Spiner, Patrick Stewart (as Jean-Luc Picard from Star Trek: The Next Generation), and Alex Trebek.

Herman stayed with the show until six episodes into the third season. When speaking about the show in 2019, he said that he wanted to leave the show to do other projects, but Fox would not let him out of his contract, as they considered him too valuable, so he got himself fired by screaming all his lines during read-through. While continuing his voice work on King of the Hill, he came across the script for Office Space, which Hill creator Mike Judge had written with Herman in mind for the part of Michael Bolton.^[4]

Herman's television credits include guest-starring on the WB's Angel and Fox's action drama 24.

Though primarily a television actor, Herman has appeared in several films, including Dude, Where's My Car?^[5] and Fun with Dick and Jane.^[6] He had a prominent role in the 1999 comedy Office Space as a gangsta rap-loving nerd named Michael Bolton who must endure questions about his relationship to the famous singer. In 2006, he appeared in another Mike Judge film, Idiocracy.

Herman is also known for his work as a voice actor in cartoons and video games, notably in Futurama, where he provides the voices of many recurring characters (including Scruffy, Planet Express's janitor; Roberto, the deranged criminal robot obsessed with stabbing people; New New York City Mayor Poopenmeyer, and Professor Farnsworth's former student and current rival Ogden Wernstrom), and King of the Hill, on which he voiced Luanne's ill-fated boyfriend, Buckley, as well as several one-shot and incidental characters.^[7][8][9]

Herman's other voice work include additional roles in American Dad!, Nickelodeon's short-lived animated series Invader Zim, the short-lived CGI-animated sitcom Father of the Pride (in which he voices Roy Horn), and the Jak and Daxter video game series. Herman starred as Ubuntu Goode (and other supporting voices) on Judge's short-lived companion series to King of the Hill, The Goode Family. He provides the voice for Mr. Frond and other supporting voices on Fox's Bob's Burgers; Mr. Gar, Brandon, and others on Cartoon Network's OK K.O.! Let's Be Heroes; The Herald and various characters on Matt Groening's Netflix series Disenchantment;^[10] incompetent park ranger Steve Williams on Comedy Central's Brickleberry;^[11] and Kevin Crawford on Paradise PD.^[12]