50. "I'm On a Boat"
Air Date: 2/7/09
Starring: Andy Samberg, T-Pain, Jorma Taccone
Who'd have thought we'd ever see an SNL bit go platinum? The flippy-floppy-sporting Andy Samberg and his boy T-Pain's nautical anthem not only became the most-watched video on YouTube the month it aired—it topped the iTunes charts and scored a Grammy nod for Best Rap/Sung Collaboration. While the Lonely Islanders unfortunately didn't leave with the award that year, their fresh vid about a trio of dudes just psyched to win a free boat ride will go down in history as one of the series' very best.