What famous musician would you want walking around your town?

Hendrix, Garcia, Joplin, Morrison.

Bruce Dickinson actually any Iron Maiden musician

Michael Jackson

I want David Byrne in my town so he and Homer can wear this around town as a visual task...
https://vignette1.wikia.nocookie.net/simpsons/images/7/71/David_Byrne_Homer.jpg/revision/latest?cb=20121218051522

NPC: Harold Hill(Robert Preston), Buddy Rich
PC: Barbra Streisand, Freddy Mecury.

Amy Winehouse.

https://www.youtube.com/watch?v=cqz08Als4xw
Sure thing: Weird Al Yankovic :)

I"d like to see Chili Peppers, Rolling Stones, and U2 who have provided some of the best musician appearances on the show. And Cypress Hill too, cuz their tasks would be hilarious

Jimi Hendrix and Van Morrison would be fun to see

Lot of great musicians listed. Good to see great taste in the forum!