Dobie Maxwell is a stand-up veteran with a knack for turning life’s toughest moments into laugh-out-loud comedy. With decades of experience, he’s mastered the art of storytelling, blending sharp wit, self-deprecation, and hard-earned wisdom to keep audiences entertained.
Born and raised in Milwaukee, Dobie’s life was anything but ordinary. His book, Monkey in the Middle—which is generating buzz for a potential movie adaptation—dives into his rough start, growing up with a drug-addicted mother who abandoned him, a father in a motorcycle gang, and a childhood spent separated from his siblings. Raised by his grandparents near 20th and Hampton, Dobie found humor in hardship, shaping the perspective that fuels his comedy today.
Despite calling himself a “dented can” and sarcastically dubbing himself Mr. Lucky, Dobie has built a successful career in stand-up and radio, working in Milwaukee, Chicago, Reno, and Los Angeles. A regular at Zanies comedy clubs in the Chicago area, he continues to bring his road-tested material to audiences nationwide. He’s also a respected comedy teacher, helping up-and-coming comics sharpen their skills with his no-nonsense approach.
From his radio gigs to his stand-up performances, Dobie Maxwell is proof that laughter is the best way to take on life’s twists and turns. Whether he’s on stage, on air, or in print, his humor is as real as it gets.
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