Haley was born in Seattle, Washington to a large Catholic family, the fifth of six children. His father was an airline executive and his mother was a homemaker and part-time maid. His father is of Irish and Italian descent, which is where he gets his Italian middle name Carlo. 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 disliked the experience so much that upon his return to Seattle 18 months later, he refused to speak the language except to translate for his younger sister, who only spoke French. He began acting as a child in the Seattle area doing community and school theater. As a teenager, he stumbled upon the film set of Scorchy (1976) in downtown Seattle. After seeing some of the movie being filmed, jumping into a few shots as an extra and meeting the star, Connie Stevens, he decided to pursue a career in show business.
At 15 he moved to rural Ellensburg, Washington. After high school, he took on several jobs, including lumberjack, hay buck, and ranch hand. He eventually enlisted in the U.S. Army to join the Green Berets. He was in the service from 1980 to 1985 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.
After his tour in the Army, he began doing stand-up comedy in his native Seattle and quickly rose to headliner status. In 1988, he moved to Los Angeles where he had immediate success, winning a "Hollywood's Hottest New Comic" competition, appearing on several stand-up comedy TV shows such as An Evening At The Improv and was picked up by ABC Television for a one-year holding deal. In July 1988, Haley was a contestant on the Alex Trebek hosted game show "Classic Concentration". His appearance spanned multiple episodes as he won $11,285 worth of prizes. However, it was his proverbial big break on The Tonight Show Starring Johnny Carson in 1990 that launched his career in earnest. His first appearance led to a flood of television and film roles and an HBO comedy special.

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