10. The Lonely Island Makes Fun of Rap, Gets Nominated for a Rap Grammy
In 2010, The Lonely Island (a pair of white guys so “edgy,” they made Malibu’s Most Wanted look like Straight Outta Compton) enlisted T-Pain to do a featured verse for their song “I’m On A Boat.” As a reminder, “I’m On A Boat” made fun of Hip-Hop. The entire song was a Weird Al-esque trip into poking fun at Hip-Hop stereotypes. And for their efforts in making fun of Hip-Hop, they got nominated for a Hip-Hop Grammy. Amazingly…they lost (to “Run This Town”).