Bailey is best known as the host of the highly successful show “Cash Cab” on Discovery Channel. Bailey has won three Daytime Emmy Awards for “Cash Cab,” (for Outstanding Game Show Host), and "Cash Cab" has won another three Daytime Emmy Awards for Outstanding Game/Audience Participation Show.
In addition, Bailey’s one-hour special “Road Rage” premiered on Comedy Central on May 21, 2011. He also was the host of NBC's "Who's Still Standing?"
Bailey got his unlikely start as a standup comedian when he was mistaken for a comic in the green room of The Comedy Store in Los Angeles, where he was hired to answer the phones. The booker, seeing that the other comics in the room could not get enough of Bailey’s humor, signed him on the spot. After a few years of performing in Los Angeles, Bailey moved back to New York and for two years, went to “open-mic” nights to hone his craft. Now with over 10 years under his belt as a successful standup, Bailey continues to perform all over New York City and has achieved international acclaim for both the show "Cash Cab" and for his comedy performances all over the world.
He has appeared regularly at comedy festivals over the years and has guest-starred on numerous television comedies and dramas, including NBC’s “Law & Order: Special Victims Unit," “Hope & Faith,” "The Knights of Prosperity”, “30 Rock”, “Oprah”, “The Today Show”, and "Mad TV." He also has a recurring role on the daytime drama "One Life to Live" and has appeared in his own “Comedy Central Presents” special. In addition, Bailey also has performed on several of the late-night talk shows, including NBC’s "The Tonight Show with Jay Leno," "Late Late Show with Craig Kilborn," NBC's "Last Call with Carson Daly" and "Comedy Central's Premium Blend,” among many others.