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Jessica Simpson, "With You" (a.k.a With Nothing But a T-Shirt On)

Song: Jessica Simpson, "Nothing but a T-Shirt On"
Context: Say what you want about Ms. Simpson, she's still a more talented performer -- and a much better human being -- than her former beau John Mayer, who plays Cricket Wireless Pavilion tonight. Maybe it's just me, but I think this song is better than anything he's done. Here's our argument for why Mayer may just be the douchiest douche who ever lived. Jessica Simpson - Nothing But A T-Shirt On

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