Brian was born into a family of four children, but the four following siblings turned it into a family of eight children (six boys and two girls). He has always credited his family for his comedy calling it a "funny family". This time in his life must have been a delightful time, yet full of the typical childhood pains that we all must bear, for most of his comedy is based on his childhood experiences and family life.

Yet becoming a stand-up comic was still not Brian's goal in life when he moved on to Heidelberg College in Ohio. There, he played football (yes, football!) and majored in accounting. After his coach recommended pouring his creativity into theatre, Brian took up drama and found a stage for his skills. In 1981, he began working at the Comic Strip in South Florida as a greeter and cook.

Brian stayed with the Comic Strip for two and a half years, moving up from greeter to opening comic all the while strengthening and tweaking his act. In 1984, Regan finally left the Comic Strip to hit the road as a "middle act" (better than the opening act, but not a headliner yet). Continuing to perfect his comedy on the road, he moved to New York City in 1986. By 1988, he was a headliner with a strong act - a winning act, winning the K-ROCK/Miller Lite Funniest Person in New York contest.

In 1992, Regan proved he had gained the comedic respect he so richly deserved when asked to perform for the University of Florida - Gainesville's homecoming in front of 80,000 people. His performance was spectacular and met with rave reviews.