"Goodbye Horses" from Silence of the Lambs (1991)
Jonathan Demme's Oscar-winning crime thriller Silence of the Lambs has one of the most dense collections of memorably unnerving scenes in cinema history. Though many of the blood-curdling bits of the film belong to Anthony Hopkins in his portrayal of cannibalistic serial killer Hannibal Lecter, long-time character actor Ted Levine deserves credit for inhabiting a role as off-putting and controversial as Buffalo Bill. In a scene no viewer can ever forget, Bill sits in the room where he sews garments made from the skin of his victims while listening to the 1988 synth pop song "Goodbye Horses" (NSFW) sung by Q Lazzarus. The scene's climactic moment of deranged narcissism is so strange and unexpected that its connection to "Goodbye Horses" has been used to elicit referential laughs ever since.
"Stuck in the Middle" from Reservoir Dogs (1992)
Director Quentin Tarantino is no stranger to using pop music in striking, ironic ways to round out his movies. The surf rock soundtrack of Pulp Fiction is legendary and he even managed to make an otherwise innocuous whistle tune into the theme of an ice-cold murderer in Kill Bill. Of all Tarantino's iconoclastic song choices, none are as memorable as his use of "Stuck in the Middle" by Stealer's Wheel as the accompaniment to the torture scene in Reservoir Dogs. The song began as a 1972 attempt to cash in on Bob Dylan's unique voice by aping it for a jaunty blues number. When Tarantino made it the favorite song of a sadistic criminal played by Michael Madsen, it's safe to say "Stuck in the Middle" lost its innocence forever.
"In Dreams" from Blue Velvet (1986)
Having your song featured in a David Lynch movie will do one of two things to it. It will either attain a level of artistic credibility that would be otherwise unattainable, as with Rammstein's signature, self-referencing metal track, or it will be permanently tainted by the dark, creepy atmosphere Lynch does so well. In the case of Roy Orbison's 1963 hit "In Dreams", nobody who sees Blue Velvet will be able to hear it without thinking of Dean Stockwell lip-synching to it as Ben in a supremely uncomfortable, menacing scene. There's nothing particularly shocking about the scene itself, but everything from the shady apartment in which it's set to the sudden violence that punctuates the rest of the movie fills the moment with dread.