Bailey was born in Bowling Green, Kentucky and raised in Chatham, New Jersey. He was born the younger of two siblings. He attended Old Dominion University in Norfolk, Virginia, before moving to Los Angeles in 1993. Standing at 6 feet 6 inches (198 cm), he was offered a job as a bouncer for The Comedy Store after bumming a cigarette from a man in the parking lot.\n', '

According to Bailey, he was telling stories with some comedians after hours at The Comedy Store when Skip E. Lowe, who was emceeing at the club, found his stories humorous and offered him an opportunity at stand-up.\n', '

Bailey is the host of the American version of Cash Cab, a TV game show played in a taxicab that Bailey drives around New York City, broadcast on the Discovery Channel. He also recently made an appearance on the new Shovio.com\'s TalkBackTV. He narrated the Discovery Channel\'s series Smash Lab.\n', '

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