Shades of Gray (2005)

Have you seen this motherf**ker?

Shades of Gray , a feature film of epic immaturity as five guys get together to blackmail their former best friend for all the horrible, embarrassing and outright disgusting things he's ever done to them. Now it's their turn. Sneaking into his place one night, they swipe Eric's "little black book" containing the names and sexual habits of the countless women he's slept with.