Haley was born in Seattle to a large Catholic family (the fifth of six children) of Italian/Irish descent. He began acting on stage as a child in the Seattle area. At the age of three his family moved to Saint-Jovite, Quebec, and he was put in a boarding home where he learned to speak fluent French. He hated the experience so much he refused to speak the language upon his return 18 months later, except to translate for his younger sister, who only spoke French. He had a turbulent childhood and, at 15, ended up living with his brother in Ellensburg, WA. As a teenager, he stumbled upon the movie set of Scorchy (1976) while wandering in downtown Seattle. After seeing some of the movie being filmed and meeting the star, Connie Stevens, he made up his mind to pursuit a career in movies.

After high school he took on several jobs, including lumberjack, hay buck, and ranch hand. He eventually enlisted in the US Army to join the Special Forces (the Green Berets). He was in the service from 1980 to 1985 (three years regular, two years reserves) where he won letters of commendation and the Army Achievement Medal, but left early to pursue a career in show business. While in the Army (1983) he was in the play Guys and Dolls starring Joe Namath at the Ft. Bragg Playhouse. His unit was deployed to Grenada three days after he was discharged from the regular Army.

After his tour in the Army he began doing stand-up in his native Seattle and quickly rose to headliner status. In 1988 he moved to Los Angeles where he had moderate success, winning a "Hollywood's Hottest New Comic" competition, appearing on several cable comedy shows such as An Evening At The Improv and was picked up by ABC television for a one year holding deal. But it was his proverbial big break on The Tonight Show with Johnny Carson in 1990 that kicked his career into high gear. His appearance led to a flood of television and movie roles and an HBO comedy special.

In 1995 he was chosen to replace Lowell the mechanic (played by Thomas Haden Church) on NBC's TV seires Wings. In 1995 he was in a Clio Award winning Super Bowl ad for Miller Lite where he played hard luck quarterback Elmer Bruker, a man that was on every winning Super Bowl team but never played. In 1997 he portrayed "The Hooded Avenger" on the short-lived Weird Al Show.

More recently he is being cast in dramatic roles, playing a detective in the Coen Brothers movie The Man Who Wasn't There and Martin Scorsese's The Departed. In 2003 he was replaced by Chris Penn in the television pilot for the CBS show The Brotherhood of Poland New Hampshire. In 2006 he returned to stand-up comedy after a long hiatus and currently lives in New York.

In February 2007 he was cast as tennis commentator Ryan in the Terrence McNally play Deuce starring Angela Lansbury and Marian Seldes and directed by Michael Blakemore In July 2008 he wrapped production of the Clint Eastwood movie Gran Torino, where he played Clint Eastwood's son Mitch.

Haley owns the Frank Sinatra booth and several other items from Chasen's restaurant.

• The Caine Mutiny Court-Martial (1988)
• Always(1989)
• Into the Sun(1992)
• Clean Slate (1994)
• Baby's Day Out (1994)
• Little Giants (1994)
• Mars Attacks (1996)
• That Darn Cat(1997)
• McHale's Navy (1997)
• The Weird Al Show (1997)
• The Thirteenth Year(1999)
• Pearl Harbor(2001)
• The Man Who Wasn't There(2001)
• The Departed (2006)

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