Wolinski grew up in Chicago, Illinois, and in the late 1960s was the keyboard player and lead singer of the band The Males and a member of the bands Shadows of Knight and Bangor Flying Circus. When the latter band broke up he helped form the band Madura, which was produced by fellow Chicagoan James William Guercio. Guercio used Madura in his 1973 film Electra Glide in Blue; Wolinksi also had a small acting role.
In the 1960s Wolinski formed a short lived band in Chicago called The Electric Band. They played regularly at a club called The Cellar.
In the late 1970s Wolinski joined Rufus as a keyboardist and songwriter. He co-wrote or solely wrote their songs "Hollywood", "Street Player" (later recorded by co-writer Danny Serephine's band Chicago), "Everlasting Love" (not to be confused with the Robert Knight hit with the same title), "Do You Love What You Feel", and the 1983 hit single "Ain't Nobody," which reached #1 on the US Billboard R&B chart.
Wolinski has worked with numerous other artists as musician, songwriter or producer, including the Bee Gees, Glenn Frey, Michael Jackson, Danny Seraphine, Beverley Knight, Millions Like Us, Stephanie Mills and Minnie Riperton.
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