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Legendary Hollywood Lotharios Bed Down In These Love Shacks

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Photos: ABC News

Back in October, we took a look at the Venice apartment that was once home to the 18th-century womanizer Casanova. But now, just in time for Valentine's Day, we're taking a look at some of Hollywood's contenders for the title of Love Master, Doctor of Love, and, of course, That-Famous-Asshole-Who-Slept-With-Me-And-Never-Called. But if Casanova's haunt was the picture of Venetian civility—with its beamed ceilings, ornate details, and elaborate sculpture—some of these modern analogs are more than a little disappointing. Come on, Wilmer, the Valley? But some, like the Italian villa owned by 1997's Sexiest Man Alive, help explain why these five gents find it so easy to to bed scores of eager women.

Yep, that's George Clooney's much talked-about Villa Oleandra, on the shores of Lake Como in Italy (above). Purchased in 2002 from the Heinz family, the villa features a lakeside swimming pool, a stone jetty, lush greenery, and fabulous interior finishes. When ABC News paid a visit, Clooney told Diane Sawyer he wouldn't sleep in the master bedroom because it's too big and joked that the master bathroom was "bigger than my apartment." We're going to go ahead and assume those days of cramped apartments are well behind him. Villa Oleandra never saw Clooney's four-year marriage to Talia Balsam, as that misadventure wrapped in 1993, but it has seen a rotating cast of girlfriends in recent years, including Brit model Lisa Snowden, cocktail waitress Sarah Larson, and Italian TV personality Elisabetta Canalis. But if any of them ever accused Clooney of being a pig, he always figured they were talking about Max, the 18-year-old, 280-pound pot-bellied pig that shared the villa until he passed away in 2006.

? While Clooney might be a heartbreaker, at least he's respectful. The same can't really be said for That 70's Show star Wilmer Valderrama, who kisses-and-tells to no end but still manages to maintain his popularity among the ladies of Hollywood. The 31-year-old actor has been linked to Lindsay Lohan, Mila Kunis, Jennifer Love Hewitt, Ashlee Simpson, and countless others. In 2006, Valderrama claimed he had deflowered teen favorite Mandy Moore, and Moore responded by calling his comments "utterly tacky," which is precisely what we'd call his taste in real estate. He has owned quite a few properties in the celebrity no-man's-land of Tarzana, Calif., including this rather heinous 4,800-square-foot architectural non-wonder. Valderrama purchased it in '03 for $1.25M and later listed it for $2.25M, so at least this Valley adventure might pay off.

? Although it might not be obvious from his relationship with actress Annette Benning, whom he married in 1992 and has four children with, but actor/producer/director Warren Beatty got around in his youth. The numbers, his biographer claims, are astronomical, and frankly unbelievable: some 12,775 women over his 72 years. But if his skills as a womanizer remained strong, some of his houses sure haven't. In 1994, his house on L.A.'s Mulholland Drive collapsed. Maybe it was all the rocking of the headboard, but official reports cite a massive earthquake. Either way, Beatty just moved on, into this 10,000-square-foot "temporary" home just down the road. But maybe not for much longer; the destroyed mansion he's owned since moving out of the Beverly Wilshire Hotel in 1972 is finally being rebuilt.

? Beatty's long-time pal Jack Nicholson hasn't been doing much in the way of building, but he's sure fond of buying. The 73-year-old acting legend has purchased four properties adjacent to his 1957 Mulholland Drive ranch house—which he scooped up way back in 1969—including the former home of Marlon Brando, which he promptly had razed, citing mold infestation.
Over the years, Nicholson claims to have bedded some 2,000 women, and if that's true, a lot of it went down here, in this relatively modest 3,300-square-foot house. It's also rumored to be the location of director Roman Polanski's ill-advised sexual relations with a minor, a crime that has kept Polanski on the run from U.S. authorities for the past three decades.

? Finally, there's the unabashed swinger and Playboy founder Hugh Hefner and his legendary Playboy Mansion, which rose to fame at the hand of Hef's scandalous parties and notoriously tight security. Hefner purchased the Holmby Hills estate in 1971 for $1.1M and has spent the last three decades entertaining thousands of naughty men and women and, of course, adding $15M in home improvements (including the famous Grotto). Today, the manse is valued at $54M. Now that Hefner is getting married, will he change his wild ways and settle down? We think not.

· Angelic Original Detailing WOWs in Casanova's Opulent Abode [Curbed National]
· George Clooney's Italian Villa [ABC News]
· Mandy Moore Calls Wilmer Valderrama A Liar [Egotastic]
· Wilmer Valderrama: Valley Boy [Real Estalker]
· Warren Beatty slept with 12,775 women, claims biographer [Guardian]
· Warren Beatty's (many) properties in the Beverly Hills, Calif. Post Office [Berg Properties]
· Jack Nicholson's (many) properties around the country [Berg Properties]
· Playboy Mansion Valued at $54 Million in Lawsuit [Bloomberg]
· Playboy founder Hugh Hefner to marry girlfriend [Telegraph]