The Most Eligible Boomer Bachelors

Whether they’re actors, politicians or entrepreneurs, these guys are some of the most sought-after boomer bachelors on the market. Here's who they are, and what's so special about them.

Andre Balazs, 54

Born in Hungary, Balazs studied both journalism and business at Columbia University, and the business classes definitely paid off. The restaurateur and hotelier is worth $450 million. Most recent girlfriend: comedian Chelsea Handler.

George Clooney, 50 He’s got a relatively new girlfriend now (Stacey Keibler) but if Clooney’s past relationships are anything to go by, she shouldn’t be dreaming about a wedding. Clooney, who’s been outspoken about his unwillingness to marry, owns a famously magnificent home on the shores of Italy’s Lake Como. He’s also been known to make a movie now and again.

Hugh Grant, 51 You might not believe this from the number of romantic comedies he’s starred in, but Hugh Grant has never actually been married. (He and Elizabeth Hurley were together thirteen years but remained single.) However, he does have a daughter, the product of a “fleeting affair” with a Chinese woman, Tinglan Hong. Most recently, Grant’s drawn attention for his off-screen denunciations of tabloid journalists in the News Corporation phone-hacking scandal.

Lindsey Graham, 56 The only federal politician on this list (which tells you how important it is to have a spouse and kids in the picture), Graham succeeded Strom Thurmond as a U.S. Senator from South Carolina. An attorney with a long record of military service, Graham served as a military prosecutor. Because he’s never been married, there’s been speculation that he’s gay, but Graham has handled that with humor and a bit of sarcasm. During an interview with "The New York Times," he said, “I know it's really going to upset a lot of gay men—I'm sure hundreds of them are going to be jumping off the Golden Gate Bridge—but I ain't available; I ain't gay. Sorry.”

Larry Ellison, 67 For a short time in 2000, the CEO of the software company Oracle was the world’s richest man. He’s come down a bit since, not that it matters. Today he’s worth $33 billion. It’s been an astounding trip for the New York City native, who was raised by adoptive parents and never finished college. He’s been married and divorced four times and once said, “I have had all the disadvantages required for success.”

Ty Warner, 67 If you’ve ever bought a Beanie Baby, you’ve put money in Ty Warner’s pocket. The little fuzzies have made Warner a very rich man ($2.4 billion at last estimate.) It all began back in 1993, when Warner mortgaged his house and invested his life savings in manufacturing Beanie Babies. Since then, he’s expanded into luxury hotels like the Four Seasons in New York City as well as pricey golf courses.

Sean Penn, 51 The abrasive actor, who’s known for his bad-boy behavior and outspoken politics, has had some rocky marital times, first with Madonna and then with Robin Wright. He’s also alienated a lot of people with his criticism of the war in Iraq. But few could argue with his relief efforts after the 2010 Haiti earthquake: Penn’s foundation operates a 55,000-person refugee camp that is by all accounts one of the country’s most efficient.

The Governator, 64 Forget the body-building career and the governorship of California. What Schwarzenegger’s most recently been known for is his scandalous split from wife Maria Shriver after his affair with a maid and the existence of their child became public knowledge. Shriver moved out of the governor’s mansion, and Arnold soon appeared with a T shirt that said “I survived Maria.” Funny, we thought it was just the opposite.

Tim Robbins, 53 Robbins raised the hopes of cougars everywhere when his long-term relationship with Susan Sarandon, 12 years his senior, looked as if it would become permanent. But the couple ended their 21-year partnership in 2009. For Robbins’ part, he’s said that his “midlife crisis” preceded the split. Whatever the reason, it’s been Sarandon who’s been making news: She’s reportedly keeping company with a guy thirty or so years younger than her.

Paul Allen, 58 Although he co-founded Microsoft with Bill Gates (and is reported to have thought up the company’s name), Allen has distanced himself from the Seattle-based behemoth for years now. But he still owns a reported 138 million shares. Now he is making his mark in philanthrophy and sports (he owns the NBA Portland Trailblazers and the NFL Seattle Seahawks.) While he’s been a bachelor his whole life, Allen, a survivor of Hodgkin’s lymphoma, told "60 Minutes," “I still want a family.”

Craig Newmark, 59 Newmark, the founder of the phenomenon known as craigslist, is as plain and utilitarian as the layout of his website. But like his site, Newmark is a lot more successful than he looks. Craigslist is among the top ten most visited sites in the world and by some estimates earns at least $10 million a month. But Newmark is more interested in pursuing political change than amassing wealth. The site has had some horrifyingly violent crimes stemming from listings; despite that, it’s still used by millions of people globally.

Jack Nicholson, 74 He’s been a bad boy for, oh, forty years or so, and he’s still going strong. Just check him out in his courtside seat at the Lakers games. The shades look cool, too. Nicholson hasn’t been married since 1968 (he was in a long-term relationship, not marriage, with Anjelica Huston) and although he seems to have slacked off in the dating department, he’s apparently still active. I “I only take Viagra,” he's said, “when I'm with more than one woman.”