Cynthia Nixon in Advice from a Caterpillar (1999)

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Cynthia Nixon is a video artist living the high life in New York City. She's got the hot art career, the requisite righteous loft, and a nice nookie hook-up with a married man. She's not looking for love, nossir . . . but love is about to find her in Advice from a Caterpillar (1999). Into her breezy urbane world waltzes Brat (Timothy Olyphant), a nice, honest actor sort who's as cuckoo for ’70s sitcoms as she is. She finds herself quickly falling for Tim, but to be with him, Cyn has to commit the greatest friendship sin—it seems that Tim is dating her best friend, Andy Dick! Now that's a dilly of a pickle. Keep your eyes peeled for Ally Sheedy to pop into this tale of triangular love tangles—unfortunately, though, it's only Cyn who shows skin in Advice from a Caterpillar . . . but that's some skin she's in! Nipple-slippin' Nixon for the win!