While Michael was in college, his parents moved to suburbs of Chicago and Michael began his comedy career at The Barrel of Laughs Comedy Club in Oak Lawn, IL. The blue-collar Southwest Chicago crowds forced him to craft funny jokes and deliver them with an authentic confidence and stage presence. To survive, Michael lived at home with his parents—which he talked about onstage to great success. Night after night, he would travel from bars to billiards halls to coffee houses to comedy clubs in and around Chicago performing his jokes. Eventually, a very talented musician, Stolie, connected him with an agent that booked college shows.
Around the same time, Michael won local contests—The Taste of Chicago Sierra Mist Zanies Comedy Challenge, the Chicago region of Comedy Central’s Open Mic Fight, and The Lucky 21—which led to frequently headlining the iconic Chicago club—-Zanies—and also led to his TV debut on Comedy Central’s Live at Gotham. Fueled by comedic stories about living at home with his parents after college, Michael made appearances on both The Late Show with David Letterman and The Tonight Show with Jay Leno within six months of each other—a feat rarely achieved by a new comic. Michael proceeded to move out of his parents’ house and onto the road touring the country performing in colleges and clubs in almost every state. While his act changed with his new surroundings, it maintained a connection to humble beginnings.