Three to Tango (1999)

The romantic comedy Three to Tango (1999) tells the story of ambitious young architect Oscar Novak (Matthew Perry). Oscar is desperately trying to get a contract with Chicago millionaire Charles Newman (Dylan McDermott), so when Newman mistakenly assumes he is gay and asks him to keep an eye on his beautiful girlfriend (Neve Campbell), he doesn’t argue. But when Oscar starts to fall for the girl and then wins Chicago’s Gay Professional of the Year, he starts to wonder if he can keep up the charade. Neve’s not nude here, but you can see the tops of her teats in a bubble bath.