Regan attended Heidelberg College in Tiffin, Ohio, where a football coach recommended to him a Communication & Theater Arts Department. Ensuing college, he work on the little comedy club in Ft. Lauderdale, Florida. Inside 1986, Regan relocated to New York City and two years late he won $10,000 whilst the local radio station known as him Funniest Human withinside Just released York in the contest.

Regan hwhen processed many televisiin appearances on such shows as The Tonight Show, The Late Show with David Letterman, Late Night with Conan O'Brien, and Dr. Katz, Professional Therapist. He tours often & has opened for Jerry Seinfeld.