Gould was born in Hopedale, MA where he was the fifth of six children. When he began college at University of Massachusetts Amherst in 1982, his attention quickly turned to open mic nights instead of classes. Never finishing school, the stand-up world consumed him full-time as he moved to Boston in 1984. Within two years, Gould was out of Boston, forming the San Francisco Comedy Condo, a three-bedroom condo that housed all sorts of comedians until 2005. After a few more years of stand-up, Gould got his first big break as a regular on the short-lived but well respected "The Ben Stiller Show" (Fox 1992-93). While the show only lasted a year, it opened up doorways to acting and writing, as Gould bounced around doing guest spots on TV shows including the sketch comedy stalwart "MadTV" (Fox 1995-2009) and comedian-driven classics "Seinfeld" (NBC 1989-1998) and "The Nanny" (CBS 1993-99). Gould's stand-up career took a hit in 2001, but only because he decided to take a job as a writer, and later a producer, on "The Simpsons" (Fox 1989-) which was in its 13th season when he came on board. He stayed on the show until 2007, winning three Emmys as a part of the heralded writing staff. His reasons for leaving were that, with a full-time job, his time for writing and performing on his own was limited. After leaving "The Simpsons," he dove back into stand-up comedy with a vengeance, releasing a few specials, including two that have come to DVD and CD. He also became a podcasting regular, guesting on several of Chris Hardwick's Nerdist podcasts and eventually starting his own show in 2012, "The Dana Gould Hour."