22. Otis Redding, 'Try a Little Tenderness' in 'Pretty in Pink' (1986)
Some of the most awesomely terrible dancing ever captured by a camera crew – and that's just part of what makes this a perfect rock & roll moment, from a perfect teen flick. Everybody loves Pretty in Pink for all the new wave John Hughes put on the soundtrack – the Smiths, Echo and the Bunnymen, OMD, etc. – but the best moment comes when Jon Cryer's Duckie serenades Molly Ringwald with his rendition of the Otis Redding soul classic. The Duckman's goofball moves cannot remotely be described as "cool," "funky" or even "human," but he needs this song to express all the bottled-up emotion he has for Molly, because he can't tell her himself. So it's slapstick comedy, but it's also true romance: a very rock & roll combo. Despite the Duckie legacy, Jay-Z and Kanye sampled this song anyway for "Otis," which was open-minded of them.