Alcroft earned a Bachelor of Science in Communication from Ohio University in 1971 and is married to two time Emmy award winning figure skating choreographer Sarah Kawahara. The couple have three children, Alysse, Hayley, and Thatcher.
Alcroft was working as a disc jockey at a Key West radio station in 1979 when cartoonist Mack Dryden left a note for him at his studio. It read, "You must be one of the funniest men in Key West; I'm the other one." The pair got to know one another and began performing as a stand-up act in Key West.
They had been working together for less than two years when they were invited to appear on The Tonight Show with Johnny Carson. That and other TV appearances led to their own syndicated show in 1985, called Comedy Break. They taped 125 half-hour shows in less than a year. Mack and Jamie continue to perform at Corporate Events around the world and have earned the reputation as Clean Comedians.
As a voice actor, Alcroft has provided numerous voices for commercials, animated series, and video games such as Gears of War I, II, and III and Call of Duty United Offensive as Lieutenant Lehmkuhl and Sgt. Ramirez. He also played the voice as the interviewer from the intro and outro of Spyro The Dragon and other numerous dragons.