Since 2005, Regan's tour has visited close to 100 cities each year. Regan was seen in the Chris Rock movie "Top Five," and he was nominated for a 2014 American Comedy Award for Best Concert Comic. In February 2014, Regan performed two sold-out shows at the 12,500-seat EnergySolutions Arena in Salt Lake City, and in August 2013, Regan sold out the legendary, 8600-seat Red Rocks Amphitheater outside of Denver.
With his first appearance on the "Late Show with David Letterman" in 1995, Regan solidified his place on the show and recently made his 27th appearance, the most of any comedian on the CBS show. Occasionally venturing off the stand-up stage, Regan recently appeared in Seinfeld's "Comedians in Cars Getting Coffee," but his main focus is stand-up comedy.