They used to be called cads, or playboys, or Kennedys—randy skirt-chasers who could be trusted to mind their manners and get their girls home by 11 p.m., even if they sometimes left them with a mild burning sensation. Jack Nicholson, the patron saint of this brotherhood, claims to have bedded an estimated 2,000 women in his lifetime. And at 69, he’s still going strong. “In terms of age,” he bragged to Rolling Stone in 2006, “you could say that over the last year, I’ve probably covered the territory from 21 to 61.”
But lately, a new strain of scoundrel is on the prowl—one that shares all of Jack’s oversize appetites and little of his lethal charm. You can find these Don Juans locked in bathrooms at Bungalow 8, hotel-hopping in St. Barth’s, or, if they’re really dedicated, forcing beauty queens to belly dance in desert sex compounds. Generally over 30, defiantly single, and immune to public ridicule, they use fame, power, and expensive sailing vessels to pursue their quarry, only to leave heartbreak and paternity suits in their wake. Call them lotharios, womanizers, or heartless bastards—just don’t expect them to call you back.
MCNASTY Colin’s pipe is calling
Notable Assets: Gaelic brogue; smoldering gaze; Marlboro breath
“When I come to town, I [bleep] everything I can”Farrell burst onto the scene as one of the hardest-partying bad boys to hit Hollywood since Jack himself: smoking, drinking, cursing, trashing, and screwing anything he could focus on long enough before passing out. Since his arrival stateside, he’s worked his way through the young and trashy set, from Paris to Britney to Lindsay, and a battery of models, including one who bore him a son. As he told W magazine, “When I come to town I [bleep] everything I can.” On the set of Alexander, Farrell—or “Cock-Out Colin” as he was affectionately known—famously showed Rosario Dawson the trailer door when pouty-lipped sex priestess Angelina Jolie turned up hungry for fresh meat. Yet for all his dirty deeds, he comes off like a teddy bear. On his sex tape with Playmate Nicole Narain, for example, Farrell describes her vagina as a “beautiful little flower” and lays on the Irish sweet-talk: “If a fucking camera could blush it would be fucking red because you are so fucking pretty.” Due to archaic bylaws, the performance cannot be considered by the Academy.
Occupation: PBS talk-show host
Notable Assets: Massive Rolodex; Southern charm; Mini Cooper convertible
Many men are pigs at heart, but in Charlie Rose’s case, it’s not just a metaphor. Last March, surgeons replaced his mitral valve with that of a swine, his second such porcine-related transplant. Rose, whose no-frills, upper-middle-brow interview show has aired on PBS since 1991, is a notoriously avid admirer of the female form. Or, as one longtime friend puts it, “He’s just a straight-up horndog.” Divorced since 1980, he favors women of substance, like Wall Street Journal publisher Karen Elliott House, LTB Media chief Louise MacBain, and Marybel Batjer, a former cabinet secretary for Arnold Schwarzenegger. From 1993 to 2005, he dated socialite Amanda Burden, though he was frequently rumored to be pursuing extracurricular interests.
At work, Rose is known for surrounding himself with attractive female producers who have been referred to, inevitably, as “Charlie’s Angels.” And while he’s on good behavior in the office, he loosens up in the Long Island village where he has a vacation home. Sources say the married men of Bellport are afraid to leave their wives alone during the summer, for fear Rose will creep into their gardens. And with good reason, as one startled half of a New York power couple learned while doing dishes after a dinner party. As the woman’s husband was enjoying dessert in the next room, the Public Bawdcaster sidled up from behind, slid a neighborly hand up her skirt, and palmed her buttock like a honeydew. No word if she received a complimentary PBS tote bag.
Occupation: Entrepreneur; manager of Renault’s Formula One racing team; owner of Cipriani London and the Billionaire Club in Sardinia
Notable Assets: 200-foot yacht; leathery orange tan
The “overweight Italian stallion” has managed to parlay his gratuitous racing fortune and hairy Buddha belly into relationships with the world’s most beautiful women, including Nicole Kidman, Elle Macpherson, and Eva Herzigova. He’s often spotted off Sardinia on his yacht, Force Blue, with bikini-clad ladies half his age. “I prefer younger girls,” he explained to the Daily Mail. “They say thank you for dinner, at least.”
But as Heidi Klum learned, free meals are a lot easier to get out of Briatore than child support or fidelity. After his dalliance with a 19-year-old model cut their romance short, Heidi’s baby daddy refused to offer financial assistance without a paternity test. A friend of Klum’s later told the Post the billionaire never “gave her a dime” to care for their daughter, though Briatore claims otherwise. Klum’s aunt tried to remain neutral, describing him to the Mail as a “wrinkly, worthless old has-been … bastard.” Naomi Campbell may have shared those sentiments when she had a tattoo of Briatore’s initials removed from her arm. Despite Campbell’s accusations of domestic abuse, they’ve continued their cycle of make-ups and break-ups. It seems, however hard he tries, Briatore is unable to commit to just one size zero. “You know how it is with women,” he told the Guardian last year. “The big excitement comes with the flirting. You flirt, flirt, flirt, and then you are there.”
Occupation: Unemployed book publisher
Notable Assets: A villa in Italy and, by her own account, a clitoris “the size of two fingers”
Regan went on testosterone therapy after she hit menopause. “I then understood how men think and feel,” she confided. “I became a sex maniac”Regan’s peerless potty mouth alone could qualify her as toxic. While she was employed at HarperCollins, her endearing habit of referring to colleagues as “pussies” and “cunts” earned her the rare distinction of being sued by female employees for sexual harassment. But that’s not surprising for a gal who liked to boast of having “the biggest cock in the building.” As if a phantom phallus and the bravado of a bullfighter didn’t make her man enough, Regan went on testosterone therapy after she hit menopause. “I then understood how men think and feel,” she recently confided on her Sirius radio show. “I became a sex maniac.”
By all accounts, she’s as good as her word. Most famously, she had an affair with former NYPD commissioner Bernie Kerik, meeting him for trysts in an apartment reserved for Ground Zero recovery workers. According to one friend, she still gushes that her sessions with the top cop were the best sex she ever had. And it’s not as though she lacks a basis for comparison. One editor, who brought a married friend from out of town to an industry Christmas party, was awed by the speed with which Regan seduced the stranger into going home with her. She also reportedly romanced Pablo Fenjves, the ghostwriter of O.J. Simpson’s scrapped quasi-confessional, If I Did It. “Men should be sexually aggressive with women,” she once told an interviewer. Judith, may we introduce you to Benicio?
BENICIO DEL TORO
Notable Assets: Played Duke the Dog-Faced Boy in Big Top Pee-Wee
If New York’s Bungalow 8 is the toxic Algonquin, Del Toro is its dyslexic Dorothy Parker. Night crawlers gossip about the “Mafia-style wad of cash” he conspicuously leaves out on his table, presumably for tipping waitresses. He’s also one of the few patrons with the right to bypass the club’s infamous bathroom line, a privilege he frequently exercises with “two and even three girls in tow.” Luckily for Benicio there’s no time limit on his stay. As one potty-goer puts it, “If the attendant knows he’s in there, she never even knocks.”
Decades-younger starlets like Scarlett Johansson and Lindsay Lohan have both reportedly fallen into Del Toro’s beefy clutches: the former in a Chateau Marmont elevator; the latter at the 25th birthday of Sara Foster, B-Del’s girlfriend at the time. Del Toro’s signature seduction tactic is “the unrelenting stare,” a libidinous tractor beam that, once locked on, is almost impossible to escape. Sadly, according to one repeat customer, the actor’s precoital intensity doesn’t necessarily translate in the bedroom: “It was kinky, but lackluster and sloppy.” Or, as another contestant recalls, “He was so messed up, we had to stop so he could go puke.” Benicio might be a boor, but he’s no animal: “He gives you $20 for a cab ride home.”