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James Brown and Lesley Gore, Ski Party (1965)
What makes sense here: transplanting the "beach party" movie to a ski resort to shake things up a bit. What makes absolutely no sense: Lesley Gore popping up to sing "Sunshine and Lollipops" on the bus, and then James Brown and the Famous Flames claiming to be the ski patrol at this Idaho ski resort. Then they break out into the whitest version of "I Feel Good" you will ever hear. Rent Get on Up to get a fictionalized behind-the-scenes look at this moment.
Count Basie, Blazing Saddles (1974)
It's 1874, and Bart (Cleavon Little) is off to become a small town's first Black sheriff. One needs a certain amount of style and encouragement to complete such a task, so Mel Brooks gives him Gucci saddlebag and the live sounds of Count Basie and his orchestra playing "April in Paris." The bandleader doesn't utter a word but his anachronistic presence says enough.
The Ramones, Rock N' Roll High School (1979)
When a high school principal attempts to prevent the Ramones' biggest fan, Riff Randell, from attending a concert, all hell breaks loose. Riff and her classmates take over the school, and the Ramones show up to join in the fun, singing through the hallways and wreaking the kind of havoc we all once dreamed of doing ourselves.
Madonna, Vision Quest (1985)
So, Madonna wasn't technically playing herself in this film about a high school wrestler (Matthew Modine) in love with an older woman, but it's as close as she ever got to doing so on the big screen before becoming a full-fledged actress. She sings "Crazy for You" and "Gambler" in a local bar in the movie, her first big-screen appearance.
Twisted Sister, Pee-wee's Big Adventure (1985)
When Pee-wee sneaks onto the Warner Bros. lot to steal back his bicycle, the chase leads him straight through Twisted Sister's video shoot for "Burn in Hell." Dee Snider and the gang narrowly avoid a head-on collision with a runaway motorboat. This is one of the most '80s things ever to happen.