Big Pimpin'

They're bad guys. Really bad guys. But somehow they've been put on a pedestal higher than the hooker with a heart of gold. I'm talkin' about the P.I.M.P.s, yo. Here are our favorite hustlers of known for big pimipin' on the big and smalls screens.

5. DJay - Hustle & Flow
He didn't just tell us "it's hard out there for a pimp..." he rapped it. DJay is the ultimate good-hearted pimp. Er...sorta. In any case, he and his rag-tag crew in Hustle and Flow made us root for the underdog - even if the underdog is workin' the corner to pay the rent.









4. Guido - Risky Business
The pimp that launched the man that jumped the couch. Joey Pants turns in a twisted an comedic turn as Guido "The Killer Pimp" in Tom Cruise's first superstar movie. He also proves that Joe Pesci doesn't own the market for small, evil and incredibly entertaining little Italians.



3. Sport Matthew - Taxi Driver
Harvey Keitel has biceps like you wouldn't believe and pimps out Jodie Foster in killer fashion in this Scorcese classic. Sure, this is Deniro's tour de force, but you can't help but acknowledge the pimpness of Keitel...nor contain your laughter at the hair, the hat and the guns.



2. Drexl Spivey - True Romance
There is nothing Gary Oldman can't do - including play a white gangsta pimp who thinks he's a black Jamaican in this Tarantino-scripted classic. One of the strangest characters of the 90s, Drexl is the dirtiest of the pimps on this list...but he's also the one I'd be most afraid of. Creep-y. Creepy.







1. Cosmo Kramer - Seinfeld
Was he really slingin' Elaine on the side? No. But Cosmo Kramer in full pimp guard is about the most memorable pimp I can recall. So out of place. So crazy. So hilarious and entertaining. If only the actor who portrayed him wasn't such a nutbag. To see Kramer in full pimp-out glory, check out this video.