Born and raised in West Virginia, Booker graduated from Magnolia High School in New Martinsville, WV in 1989.

In 1992, he began his self-described "gypsy years radio tour", where he held the positions of on-air personality and music director at a number of different stations as both Chris Booker and Booker Madison in Myrtle Beach, South Carolina, Florence, Kansas City, and Pittsburgh.

[2] In 1996, he landed the evening slot at 92.3 K-Rock in New York City, where he met the nation's top radio talk show host, Howard Stern, who made the young DJ a regular on his program.

Booker eventually found his way back to K-Rock in 2005, where his show aired in the afternoon until the format was changed to "Free FM" talk.

On May 23, 2008, Booker was fired as the morning show host on "Q102" in Philly (but was still considered an employee of "Q102", due to contractual reasons).

[citation needed] Booker returned to K-Rock 92.3 FM in NY for the afternoon drive (2–7 pm) on January 7, 2009.

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