In 1999, his Comedy Central Presents special aired. He wrote, directed and starred in the short film Borrowing Saffron (2002), which co-starred H. Jon Benjamin. He's made a variety of guest appearances on shows like Dr. Katz, Professional Therapist, Home Movies, and Aqua Teen Hunger Force. Over six years he made 16 appearances on Dr. Katz, appearing as himself in the first two appearances. He then played recurring character Todd the video store clerk and appeared in most episodes in the show's final year. He also played a character in the television pilot Saddle Rash along with Sarah Silverman, H. Jon Benjamin and Mitch Hedberg. In "The Third Conchord", the twelfth and final episode of the first season of Flight of the Conchords, Barry played Todd, a bongo playing megalomaniac, who tries to introduce the highly suggestive song, "Doggy Bounce," to the Conchords' repertoire, and a new band name: The Crazy Dogggz.
The subject of his solo show Icky describes the "merciless, unpitying trouncing he suffered" on alt.fan.conan-obrien, the Conan O'Brien newsgroup, following a guest appearance.