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"Lazy Sunday" (2005)
An early gem. The trio's second SNL sketch ever became a viral sensation overnight. It follows their Sunday matinee adventures to see The Chronicles of Narnia in theaters.
"Dick In A Box" feat. Justin Timberlake (2006)
This R. Kelly sex-song knockoff is about giving your lover your penis dressed up as a holiday present. Kristen Wiig and Maya Rudolph star as the, um, lucky ladies, and JT knocks it out of the park. Would you believe us if we told you this snagged an Emmy?
"Natalie's Rap" feat. Natalie Portman (2006)
Natalie goes gangster in her rap debut. Here, she pretends to shed her good-girl image. We have to hand it to Portman on this one — she did an incredible job with gross (but amazing) lines like, "All the kids looking up to me can suck my dick," and, "I bust in dudes' mouths like gushers, motherfucker." Lovely.
"Ras Trent" (2008)
This one skewers the stereotypical white college kid (played by Samberg) that appropriates Rastafarian culture — accent, dreads, clothes, and all. The over-the-top offensive stereotyping is entertaining, but gets a valid point across, too. Sample lyrics: "Excuse I for my skanking / Give thanks and praise / Me toil part-time / At jah Cold Stone Creamery."
"Jizz In My Pants" (2008)
This single from The Lonely Island's debut album, Incredibad, is about early ejacluatlion, of course. It's crude, lewd, and disturbingly easy to get stuck in your head. Each verse gets sillier: "When Bruce Willis was dead at the end of Sixth Sense I JIZZED IN MY PANTS / I just ate a grape and I JIZZED IN MY PANTS."