4. D*** in a Box (2009)
Has a man ever walked up to you with a gift box on his crotch? If so, you may thank this Emmy award winning Samberg sketch. "D*** in a Box" was the first of three 90’s R&B style sketches featuring Samberg and Justin Timberlake. The two follow up sketches, "Mother Lover" and "3-Way (Golden Rule)" are likely lesser known, but similar in style and humor. This short became an instant classic when it was released. It’s difficult not to laugh at how ridiculously Timberlake and Samberg are dressed.
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