The Break-Up (2006)

The blockbuster romantic comedy The Break-Up (2006) paired the then real-life A-list lovers Jennifer Aniston and Vince Vaughn as a live-in couple attempting to disassemble their romance while continuing to dwell under the same roof. Set in Vince's hometown of Chicago, he plays Gary Grobowski, a Windy City tour guide fighting with his art gallery manager girlfriend Brooke (Jennifer Aniston). Brooke's the tight bodied but uptight perfectionist, while Gary's the slovenly, sports obsessed man-child, and soon enough these two vastly different personalities begin to clash. When things come to a head and they break up, they're both too stubborn to move out, so they resort to petty tactics hoping to make the other leave. When all is said and done, will these crazy kids get back together or is the relationship irreconcilable? If you want to know why, in the end, Gary's the one dying to win Brooke back, the answer's simple: baby got back! Plus a great rack! At one point, sick of his attempts to turn the apartment into a frat house Brooke decides she'll wax her vag and go for a naked stroll just to get him worked up. So, fifty-seven minutes in, Jen struts down a hallway bare-butted, requiring that the rankings of world-class cinematic rumps be recalculated. To quote Ron Burgundy, "You have an absolutely breathtaking heinie. I mean that thing's good. I wanna be F*R*I*E*N*D*S with it!" There's also a shot of Jen looking nippy as is her trademark, in a tight tank top. We needed a scene with some makeup sex, but that wasn't in the cards for The Break-Up. Still, after seeing Jen tease Vince with that body, let them break up, and break Mr. Skin off a piece of that!