I saw that Bill Wyman of the Rolling Stones has a new book, "Rolling with the Stones". Incredibly, he's 66 years old. Since he retired, he may be the only sane member of the group. It made me start thinking of my favorite entertainers/bands of the last five decades.
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Entertainer
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50's Elvis Presley
60's Janis Joplin
70's Joni Mitchell
80's Bruce Springsteen
90's Sarah McLachlan

Band
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50's Buddy Holly and the Crickets
60's Crosby, Stills, Nash, & Young
70's Jethro Tull
80's U2
90's Depeche Mode