Poetry held his interest early on, but by his teen years he had switched to hip-hop and written a rap for the graduation ceremony of his school's anti-drug program. Going to see Steven Wright on his 16th birthday steered Birbiglia toward standup. He would be writing quirky one-liners in the Wright style all the way up to his early years of college in the Washington, D.C., area. He began working the ticket window at the D.C. Improv, and there he decided to develop his Wright-like act into something more real and biographical. After studying the work of Woody Allen and Richard Pryor, Birbiglia developed a mix of one-liners and personal stories that would instantly connect with audiences. He refined his act around D.C. before moving to New York City and taking any gig he could get.

A successful night at the Comic Strip Live introduced Birbiglia to the club's general manager and talent coordinator, the late Lucien Hold, who set up a string of shows that introduced the comedian to talent scouts and helped him land a David Letterman appearance. Success snowballed from there and soon Birbiglia was touring nationally, appearing regularly on the Bob & Tom radio show with his "My Secret Public Journal" segment, and developing projects for the Comedy Central network and record label. In 2004, Dog Years became his debut album for the label. His fan base grew quickly and soon indie-style T-shirts quoting Birbiglia routines were virally spreading the word. As "Cracker, please" and "Only we can call each other Cracker" shirts were being spotted on hipsters, the comedian returned with the CD/DVD combo Two Drink Mike in early 2006. Based off his blog of the same name, My Secret Public Journal Live appeared in 2007. Birbiglia opened his first off-Broadway show, Sleepwalk with Me, the following year, and spent the rest of the decade spinning that show into different projects. An accompanying nonfiction book, Sleepwalk with Me and Other Painfully True Stories, appeared in 2010, followed one year later by the album Sleepwalk with Me Live. Another stage show, Mike Birbiglia's My Girlfriend's Boyfriend, opened that March. ~ David Jeffries