I guess the most famous would be Oprah Winfrey. She wasn’t born in Milwaukee, but spent the vast majority of her childhood and adolescence there. I know where her old house is, and yes, it is in the GHET-TOE, straight up. Her family was poorer than mine – and we were pretty poor!
Eric Benet – R&B singer, ex-husband of Halle Berry
Gene Wilder – actor (he lived in the neighbourhood I grew up in 40 years before me.)
Kristen Johnston – actress (the tall redhead on 3rd Rock from the Sun – she graduated from my high school a few years ahead of me)
Speech from 90s rap band Arrested Development.
Al Jarreau – Jazz singer
Jane Kaczmarek – actress (“Lois” on Malcolm in the Middle)
Bob Uecker – basballer, sports commentator and sitcom actor (Mr Belvedere)
The Violent Femmes – I used to watch them rehearse if I walked past Brian Ritchie’s house after school when I was a kid, and one of my friends dated Gordon Gano.
Jerry Harrison – Talking Heads keyboardist
And of course, the infamous Jeffrey Dahmer.
Chris Farley is from Madison, ~70 miles east. I’d love to claim Orson Welles, but he’s from Kenosha, ~30 miles south.