Michael was born in South Orange, New Jersey. He attended Catholic school, which would shape much of his future songwriting. He was a fixture in Chicago's folk music scene for five decades. Rolling Stone magazine once called him “The greatest songwriter in the English language.”
His song The Dutchman was popularized by Steve Goodman, and covered by Liam Clancy, Jerry Jeff Walker, Celtic Thunder and Trout Fishing in America. He was also known for his whimsical songs such as Zippy, Famous in France, and Move Over Mister Gauguin.
Michael was an acclaimed theatrical composer and performer. His score for Steppenwolf Theatre Company’s The Grapes of Wrathdrew critical praise when it debuted in 1988. Traveling to Broadway, California and London, the production won two Tony awards.
Michael had three younger sisters and a brother, and they were the basis for his autobiographical play, Michael, Margaret, Pat and Kate, originally presented at Victory Gardens. The play is his story of his upbringing and family relationships surrounding his father's early death.
He reportedly didn’t want a funeral or any online RIPs. According to the Sun-Times, all he wanted, Jamie O’Reilly — his agent and a frequent musical collaborator — said he told her, was this: “If people sing my songs after I’m gone, they need to get the chords right.” In 2009, he received a Lifetime Achievement Award at the Woodstock Folk Festival, and in 2010, he received the Hans Christian Andersen Award for his adaption of The Snow Queen, for which he also wrote the music.
Michael and his wife, singer Barbara Barrow, were together for 52 years until her death in February of 2020 from complications of Parkinson’s disease.