Winslow was born in Spokane, Washington, the son of Verdie and Robert Winslow. He grew up at Fairchild Air Force Base near Spokane, and later attended the Lisa Maile School of Acting, Modeling and Imaging.
According to his own account, Winslow had few friends growing up. To pass time, he would imitate the sounds of engines, animals, flatulence, anything that made noise. Following high school and college he performed in nightclubs and theaters, where his sound imitation skills won him positive appraisal and enough money to move to and perform his act in Hollywood.
His first television appearance was on The Gong Show in which he squeezed in sound-alikes of Benji the movie dog, Star Trek, and Jimi Hendrix's "Purple Haze". He is best known for his role as Larvell Jones in the Police Academy series of movies and TV shows. He was cast in the role after he was seen opening for Count Basie. In 1985, Island Records released a 12" of Michael Winslow entitled "I Am My Own Walkman". The song peaked at number 60 in Australia.

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