Born just outside Boston, Wright attended Emerson College. After graduation in 1978, he combined the city's love of both elevated thinking and working-class attitudes and created a unique standup routine. He became the breakout comedian at Boston's legendary Ding Ho Comedy Club (a Chinese restaurant by day, comedy club by night) where in 1982, executive producer Peter Lassally saw his act and invited Wright to appear on The Tonight Show. A hit with both host Johnny Carson and the audience, Wright was invited back to The Tonight Show just a week later. In 1985, his HBO special I Have a Pony became an instant hit while its accompanying album, released on Warner Bros., won the Grammy Award for Best Comedy Album.

Playing a dentist in the 1985 film Desperately Seeking Susan kicked-off his acting career, while 1988 saw Wright co-write and star in The Appointments of Dennis Jennings, winner of the Academy Award for Live Action Short Film at the 61st Academy Awards. His second HBO special, Wicker Chairs and Gravity, arrived in 1991, then in 1992 he began a recurring role on the television sitcom Mad About You. In 1999, he wrote, directed, and starred in the short film One Soldier, then in 2006 he released his television comedy special When the Leaves Blow Away, this time on the Comedy Central cable network. The special was released on album a year later as I Still Have a Pony. He joined the televised talk show The Late Late Show with Craig Ferguson as regular guest in 2009, helping the host sift through viewer mail. In 2011, he joined the cast of Louis C.K.'s sitcom Louie, playing himself, a role he reprised from the TV show The Larry Sanders Show (1994), along with the films Half Baked (1998) and Coffee and Cigarettes (2003). ~ David Jeffries