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D*ck in a Box
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It wasn’t the first Digital Short but it gave a boom to The Lonely Island era of shorts. Winning a creative Emmy award (for a song containing the word “d*ck” sixteen times). It was the second time Justin Timberlake hosted/musical guested the show but proved his comedic timing wasn’t a fluke and spawned 2 more musical collaborations featuring the 90s R&B characters he popularized with Andy Samberg.
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