Raised in Hopedale, Massachusetts, Dana began performing comedy onstage at age 17. After high school, he studied communications and theatre at the University of Massachusetts Amherst, but after a year moved to San Francisco to pursue a career in comedy. It was there he, along with fellow comedian Alex Reid, founded the San Francisco Comedy Condo in 1986.
Gould wrote and performed on The Ben Stiller Show; one such sketch features Gould as Otto, Cupid's twisted brother, whose arrows convince a young man to fall madly in love with an elderly woman. Another series of sketches features a heavily disguised Gould as Wilford Brimley advertising "Grady's Oats" (a parody of Brimley's Quaker Oatsadvertisements). In one, he speaks of his Uncle Ray's hobby of dressing in a pink taffeta gown and filling his panties with oatmeal; in another, he brandishes a revolver through the window at children. He also appeared in an episode of MADtvas Newt Gingrich and on one episode of Seinfeld ("The Junk Mail") as "Fragile" Frankie Merman, Jerry's childhood friend (aka "The Summer George"). He co-created and was executive producer on the MTV series Super Adventure Team. In addition Gould's stand up material was featured in Comedy Central's animated series Shorties Watchin' Shorties.
In 1998, Gould appeared in the episode "Supermarket Story" of the sitcom The King of Queens. For seven years he wrote for The Simpsons, one episode of which he provided the voice of Don Knotts as Barney Fife (an impression that originated in his standup routine). He left the show in late 2006 in order to focus on his own screenwriting, though he served as co-executive producer on seasons 14 through 18.
Gould had a featured cameo in the 2003 film Girls Will Be Girls, in which he played a hit-and-run victim who admits to his alcohol problem after having a desperate one-night stand with aging C-list actress Evie Harris, the other driver in the car accident. He was also featured in the film The Aristocrats, where, among other commentary, he presents an Amish version of the eponymous joke. His short films, Last Man On Earth, Break On Through With J.F.K., A Night On Java Island, and Soul Mates are also available for download on his site. Except for the latter, all feature Gould in acting roles. 2009 saw the release of his new stand up special, "Let Me Put My Thoughts In You" on Shout Factory.
Gould provided the voice for the title character in the U.S. versions of the Gex video game series and the UK version of the first game. Gould, with his frequent writing partner Rob Cohen, wrote the majority of the jokes for the games.
He was a regular contributor to the Adam Carolla radio show where he did impressions of Huell Howser. He appears occasionally on The Adam Carolla Show podcast. The first episode of Gould's own podcast, The Dana Gould Hour , was made available on iTunes on January 31, 2012. Recurring guests include comedians like Eddie Pepitone, and each episode revolves around a singular theme. Currently, a new episode of The Dana Gould Hour is released about every two months.
In 2010, he appeared in live action on the Family Guy episode, "Brian Writes a Bestseller".
In 2013, Gould appeared with Melinda Hill and Scott Shriner in an episode of the web series Romantic Encounters. He also frequently performs live shows with comedian Arden Myrin as "The Tinkle Twins."
In 2014, Gould participated as a comedian on Playboy's "Foursome: Walk of Shame" where he joined other comedians in making fun of the program's contestants.