Whipped (2000)

The tagline for the hilarious 2000 R-rated comedy Whipped is "Never underestimate a woman." The woman in question is Mia (Amanda Peet), and considering she is woman enough to take on three hotties at the same time, underestimating her is the last thing we would ever do! Whipped is about three womanizing NYC besties who meet up regularly to trash-talk the ladies they date. However, they are put in their place when all three men start dating Mia at the same time. How much are the boys willing to endure in order to walk away with the ultimate prize - Mia? Sadly she doesn't get anyone out of their clothes here, but we do get to enjoy Brian Van Holt and Jonathan Abrahams in various states of undress. You bring the whip, we'll bring the ball gag!