The 11 Best Comedian-Musicians

From Russell Brand and Jimmy Fallon to Margaret Cho, this crowd is adept at both joking and singing on stage

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Andy Samberg/Lonely Island

Childhood friends Andy Samberg, Akiva Schaffer and Jorma Taccone had been making joke songs under the name The Lonely Island since 2001, but the comedy crew hit it big four years later when they got the attention of SNL head Lorne Michaels. All three were asked to join the SNL team, Samberg as a featured player and Schaffer and Taccone as writers. Since then, their star-studded SNL Digital Shorts — featuring everyone from demure Natalie Portman spitting rhymes about "bustin' dudes mouths like Gushers" in "Natalie's Rap" to T-Pain Auto-Tuning the nautical "I'm On a Boat" — have become one of the most popular and viral segments of the show. In 2007 they won an Emmy for "Dick in a Box," an instant hit starring Samberg, Justin Timberlake, bad dance moves, worse facial hair and their junk wrapped in gift boxes.

Video: The Lonely Island, Inside Andy Samberg's Mind Squad

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