In 1989, Bagley began studying with The Groundlings, and was soon writing and performing with their prestigious Main Stage Company. Although he retired from the theatre's Main Company in the mid 1990s, Bagley still comes back regularly to perform in The Groundlings’ all-improv show Cookin' with Gas. In 1995, Bagley left the Groundlings and turned his attention to television. After guest appearances on Diagnosis: Murder and Seinfeld, he landed his first regular role on the Showtime series Howie Mandel's Sunny Skies.
Since breaking into television in the early 1990s, Bagley has become a familiar face on primetime television. He has guest starred on such shows as Seinfeld, Wings, Dharma & Greg, According to Jim, Curb Your Enthusiasm, The X Files, Suddenly Susan, ER, Ellen, 3rd Rock from the Sun, The Nanny, and Desperate Housewives.
Bagley has also had regular and recurring roles in such hit shows as The King of Queens, Hope & Gloria, Strip Mall, and 7th Heaven, and portrayed fellow OCD sufferer Harold Krenshaw on Monk for several episodes, often antagonizing the titular character, Adrian Monk and his assistants, Sharona Fleming and Natalie Teeger. He also appeared in "Grimm" as a blutbad. He is perhaps best known on television for his appearances as Larry, one half of a married gay couple with an adopted daughter, on the hit sitcom Will & Grace.

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