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Which Movie Pimps and Madams Make Good Bosses?

In Love Ranch, out in theaters today, Helen Mirren plays a madam who, along with husband Joe Pesci, runs the first legalized brothel in Nevada. Now, while the wise words of Pretty Woman’s Vivian (Julia Roberts) are certainly true — “It’s not like anybody plans this; it’s not your childhood dream” to become a prostitute — Love Ranch did get us thinking, if you had to become a prostitute, you could do a lot worse than having Helen Mirren as your boss. But could you do better? We evaluate twelve of the more interesting fictional pimps out there to determine which would be best, and worst, to work for.

Management Style: As Times Square pimp Fast Black, Morgan Freeman rules with a velvet fist. When he gets caught up with a reporter (Christopher Reeve) who has fabricated a story the police believe is about Black, he’s all jovial banter (“Sure I watch the news!) until he shoves a gun into Reeve’s face. Downside: Murderer; threatens his employees with broken glass bottles (“It’s not your face. It’s my face”). Upside: Delivers all threats with a really soothing voice. Good Boss? He knows his business, but murder and glass bottles are best avoided.
Management Style: Crazy like a fox. Drexl is a truly unhinged pimp, into drugs, violence, and the misapprehension that he’s African-American. Downside: As previously mentioned, crazy; dreadlocked; drug trafficker; chair thrower; depending on how seriously you take dreams, Elvis doesn’t like him. Upside: Fun to watch, from a safe distance. Good Boss? No.
Management Style: Sport (Harvey Keitel) shamelessly pimps out underage girls on the grungy streets of pre-gentrified East Village, Manhattan; when his charges are feeling bad and not in a trick-turning mood, he manipulates them by sleeping with them himself. Downside: Says and believes things like, “Well, take it or leave it. If you want to save yourself some money, don’t fuck her. ‘Cause you’ll be back here every night for some more. Man, she’s 12 and a half years old. “ Upside: Does not usually beat up his girls; is a Libra. Good Boss?: We’re going to defer to Travis Bickle’s judgment on this one, and say no.
Management Style: Ultimately, Guido, known best as Guido the Killer Pimp, is just in it for the money. Sure, he makes threats, but he wants the cash more than the violence and is willing to negotiate to get it. As he tells young Joel, “If I didn’t have any self-respect, it wouldn’t just be the furniture, it’d be your arms, your legs, your head.” Lucky for Joel. Downside: Like most people in it for the money, he lacks heart; furniture thief; insists you pay your debts. Upside: Avoids violence. Good Boss? On paper, he’s not so bad; in person, he’s an intolerable creep.
Management Style: Chuck (Henry Winkler) and Blaze (Michael Keaton) are accidental pimps. Morgue workers who have the bright idea of using the office as a brothel, they’re like an eighties version of the Apatow gang: Chuck is uptight and tortured! Bill is horny! They’re both sort of nice guys! If you stick with them it’ll all work out, but only after dozens of snafus. Downside: They’re hapless; they can’t agree on anything; dead people watch while you work. Upside: Blaze is funny; Chuck’s good-hearted. Good Boss?: As far as pimps go, they could be far meaner, but also a lot more savvy. Sure, they have the space, but you didn’t get into this business to work for nerds, did you?
Management Style: Formerly pimp of the year, Fly Guy’s glory days are behind him. He now wanders through the streets of Keenan Ivory Wayans’s spoof of blaxploitation films — in which an epidemic of gold chains is killing hustlers — in the most over-the-top, hopelessly out-of-date pimp gear imaginable. Downside: You don’t get to be pimp of the year just for your clothes. (Okay, in his case, maybe you do). Upside: You could stare at the goldfish in his platform shoes for hours and hours. Good Boss? Guys, he has an aquarium on his feet!
Management Style: Ineffectual. Tanya is way too nice to be a pimp. Yes, it was her idea for Ray Drecker to put his extra-large penis to use, but after that moment of insight, she’s been more or less useless. She’s incapable of being mean and can’t even procure janes, a job that has now been outsourced to a third party. Downside: She doesn’t do anything. Upside: She doesn’t do anything. Good Boss? Really depends on whether or not you’re a self-starter.
Management Style: Don’t ever let it be said that T.J. Hicks is not open-minded! When fish-tank repairman Deuce Bigelow needs to cobble together some cash, Hicks looks at him — and, mind you, Deuce bears a strong resemblance to Rob Schneider — and has the imagination to see a prostitute. Downside: Takes offense easily; has used the word “mangina”; hits people; obsessed by others’ penis size; will eat French fries out of the toilet. Upside: Dedicated friend; so open-minded he has prostitutes in walkers: extra nipple. Good Boss? What he lacks in equanimity, he makes up for in loyalty and awesome observations about fried chicken and waffles.
Management Style: Dolemite’s a general. In jail on a frame-up, he’s let out early to clean up the streets, and with the help of an army of his martial arts–schooled prostitutes, he does exactly that, because “he’s bad, the man is out of sight, he’s a tough mother gun, the man’s name is Dolemite.” Downside: He really is tough, and doesn’t shy away from violence; also, he likes to hear himself talk, as you can see here. It is impressive, but it does go on. Upside: If you work for him, you learn martial arts; he has a theme song. Good Boss? Um, he has a theme song! (We are really suckers for musically minded pimps.)
Management Style: For Doctor Detroit, pimping is therapy. When nerdy medieval professor Clifford Skridlow accidentally agrees to look out for four very self-possessed, high-class call girls, he has to put on some crazy-ass clothes, convince people he’s a man to be reckoned with, and tap into a bold persona he never knew he had. Pimping changed his life for the better. Downside: Wears a terrible, teased, Andy Warhol–ish wig; talks in a really high voice; cannot dance the robot. Upside: Chivalrous; knows how to fence; James Brown approved. Good Boss? It’s nice to see chivalry isn’t dead, even if it is wearing horrible clothes.
Management Style: Pimp turned rapper Djay (Terrence Howard) insists it’s “Hard Out Here for a Pimp,” but his previous single, “Whoop that Trick,” indicates, correctly, that it’s equally hard out here for one of his girls. Djay has a temper problem, especially when he feels disrespected, but responds well to both loyalty and flattery — which doesn’t mean he’ll let his girls stop working, just that he’ll make them feel like they’re in this mess together. Downside: Liable to beat you, kick you out of the house, or shoot you if you sass him; will insist you strip if you’re not turning tricks; doesn’t have air conditioning in his car. Upside: Will let you sing catchy hook on his songs; is genuinely concerned about your larger spiritual journey. Good Boss? Have you heard that song? He’s forgiven for the temper.
Management Style: Though Dolly Parton’s Stangley is a micromanager with a list of rules — no drinking, no bad language, no tattoos, no married ladies, no chewing gum, no using the phone, no messiness — if you follow them, you can sing and dance around the cleanest, friendliest fictional whorehouse that ever was. Downside: All those rules; disdains pimps without recognizing she acts as (the very nicest) one; unsettlingly positive outlook that doesn’t recognize there might be something, anything, unseemly or unpleasant about the oldest profession, though, granted, this is more a side effect of existing in a movie musical than psychosis. Upside: “She pays the food and the rent and the utilities”; all that singing! Plus, she’s thoughtful enough to buy her best john (Burt Reynolds) jockey shorts. Good Boss? Runs a close second to Helen Mirren as the ideal madam.
Which Movie Pimps and Madams Make Good Bosses?