Mind the Gap

Russell Simmons & More Cradle-Robbers

Russell Simmons is dating a woman 29 years younger. See more of Hollywood’s cradle robbers.

Russell Simmons

Age might be nothing but a number, but 29 years is a pretty big number. That’s the age difference between Russell Simmons and his girlfriend, model Hana Nitsche. He joins other Hollywood May-December couples from Harrison Ford-Calista Flockhart (22 years), Kelsey Grammer-Kayte Walshe (27 years) and more. See photos.

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Russell Simmons and Hana Nitsche: 29 Years Apart

Russell Simmons loves himself a younger woman. The music mogul’s ex-wife Kimora Lee is 18 years his junior. But recently, the 55-year-old was spotted getting cozy with an even younger woman: 26-year-old German Model Hana Nitsche. This December,their love was really on display. The two hit Miami for Art Basel but spent most of their time at the beach, attracting attention both in the water and on the sand. This isn’t Simmons’s first time dating a 26-year-old. Just this summer he was linked to Leila Lopes, Miss Universe 2011.

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Dick Van Dyke & Arlene Silver: 46 Years Apart

Octogenarian Dick Van Dyke is known for his cheerful smiles and upbeat song and dance numbers—and it seems the actor’s sunny personality has won him the affection of 40-year-old Arlene Silver, a makeup artist Van Dyke met backstage at the SAG Awards six years ago. In an interview with Rumorfix, Van Dyke recalled meeting his new wife: “I was in the green room and she passed through and I was bowled over by her beauty.” Van Dyke hired her as his own makeup artist and the two dated for years (“She keeps up with me,” Van Dyke assures well-wishers). Then on February 29, the couple spontaneously decided it was time to tie the knot. “Kinda spur of the moment, we just decided Leap Day would be the best time to do it,” Van Dyke chortled happily during the interview. His new wife seems just as enthusiastic about the union: “He’s the happiest person I ever met. He’s got an infectious spirit—always singing, always humming, always in a good mood.”

Krista Kennell, Sipa / AP Photo

Harrison Ford & Calista Flockhart: 22 Years Apart

Sparks flew when Harrison Ford and Calista Flockhart met at the 2002 Golden Globes, after the Ally McBeal star spilled her wine on Ford. "She certainly did not spill a glass of wine on me," Ford told People in a joint interview with Flockhart in 2003. She interjected, "We were having a conversation for maybe 20 minutes before the wine spilled, and the truth is, Harrison spilled the wine!" Sounds like a classic seduction scene from one of Ford's Indiana Jones films. Age was never an issue for the pair, who married after eight years of dating, in June 2010. "It doesn't faze me," Flockhart said back in 2003. "Sometimes I even say, 'Wow, I keep forgetting that he's [22] years older than me.' It doesn't factor into our relationship at all."

Picture Perfect, Rex Features / AP Photo

Bruce Willis & Emma Heming: 24 Years Apart


Things didn't work out between Bruce Willis and his first wife, Demi Moore, but luckily they both found love after divorce—with partners half their age. Willis met his current wife, Emma Heming, in 2006, when he picked out the former Victoria's Secret model from a crowd of other female contenders to be an extra in the 2007 film, The Perfect Stranger, which he starred in alongside Halle Berry. He had once begged his former assistant turned executive at his production company to "punch me in the face" if he ever said he was getting married again. But he ate his words in 2009, when he tied the knot with 32-year-old Heming. "I went from 'F--- love' to 'Love is truly the answer,'" Willis told W magazine in 2009. Not surprisingly, the hot and heavy couple has no problem with PDA. "We're sickening. We make out in public," said Willis.

Evan Agostini / AP Photo

Donald Trump & Melania Trump: 24 Years Apart


The Donald—a nickname his second ex-wife, Ivana, once laid claim to—reportedly met his current wife, Slovenian Melania Knauss, at a fashion event in 1999. They dated for six years before getting hitched in February 2005, when Donald was 58 and Melania was 34. In typical Trump fashion, the pair had an over-the-top wedding in Palm Beach, Florida, where some 10,000 white flowers were delivered from New York at the bride's request. The wedding was a lavish affair, but the ceremony was traditional and their vows were "serious," said Melania. "We completely forgot everything around us," she told People in 2005. Roughly a year later, the real estate tycoon and his model wife had their first child together, Barron William Trump.

Evan Agostini / AP Photo

Michael Douglas & Catherine Zeta-Jones: 25 Years Apart



Longtime Hollywood A-list couple Michael Douglas and Catherine Zeta-Jones have the same birthday—25 years apart. When the acting legend met Zeta-Jones at a film festival in Deauville, France, he told AARP magazine he said, "I want to father your children." The actress calmly retorted, "I've heard a lot about you. It's nice to know it's all true. Good night." Though Douglas thought he blew it when Zeta-Jones stormed off, he sent her a bouquet of roses and a note that read, "I apologize if I stepped over the line." Zeta-Jones told Us Weekly that just "months later, we were dating, and I was already in love with him," despite their age difference. The couple married in 2000 and, true to his word, they now have two children. When Douglas revealed he was suffering from throat cancer in August 2010, Zeta-Jones was by his side, and he is now cancer-free. Though the stress took a toll on the actress—who admitted she was treated for bipolar disorder this past year— Douglas says he's grateful for his family's support. "I never anticipated starting a family and the joy of raising kids at my age," he told AARP.

Lynne Sladky / AP Photo

Céline Dion & René Angélil: 26 Years Apart


Songstress Céline Dion was a mere 12 years old when she first met her now-husband and manager, René Angélil, who was 38 at the time. He believed in Dion so much that he mortgaged his house to finance her debut album, but the two didn't begin dating until 1987, when she was 19. They kept their relationship a secret because of their age gap. But four years later, they got engaged; three years after that, they married; and now, the couple has three children together. "He was the man I wanted," Dion told Hello! magazine of Angélil. "I didn't want a younger man, I wanted him. And I only wanted to be his."

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Kelsey Grammer & Kayte Walsh: 27 Years Apart


The Emmy-winning star of Frasier has long had a penchant for young blondes—he's been married four times, the longest to The Real Housewives of Beverly Hills star and former Playboy model Camille Grammer. But in 2010, the actor left the mother of two of his four children for his pregnant girlfriend, Kayte Walsh, a British Virgin Atlantic flight attendant 26 years his junior. Despite Grammer's not-yet-finalized divorce from Camille and Walsh's miscarriage, he proposed and began planning his fourth wedding to Walsh at the Plaza Hotel. Fifteen days after his divorce from Camille was finalized—and 14 days after his daughter, 27-year-old actress Spencer Grammer wed—he and 29-year-old Walsh walked down the aisle. At 56, according to The Daily Mail, Grammer is two years older than Walsh's father, a former professional soccer player. But for Kelsey and Kate, apparently age ain't nothin' but a number. "I've never been happier in my life," he told People magazine.

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Linda Hogan & Charley Hill: 30 Years Apart


When VH1 reality stars Hulk and Linda Hogan announced they were divorcing in 2007, they both rebounded with younger companions. The now-57-year-old wrestler wound up marrying his now-36-year-old girlfriend, and his now-52-year-old ex, Linda, has since found herself in the arms of the now-22-year-old Charley Hill, who was only 19 when they started seeing each other. The two became engaged in June 2010 and plan to wed this summer on Linda's yacht, " Alimoney" [sic]. But The Hulk does not approve. "You live half a mile from the 20,000-square-foot home you can't go to anymore, you're driving…and see a 19-year-old boy driving your Escalade, and you know that a 19-year-old boy is sleeping in your bed, with your wife," Hogan told Rolling Stone. The nearly 30-year age difference doesn't sit well with Hogan's daughter Brooke, who told E!, "I personally don't like it at all or condone it, but she's my mom, so I have to show her support." The Hogan scion added: "I went to school with [Charley]. He was a grade under me...Me and Nick [Brooke's brother] know him well. Me and Nick are two years apart, and he was right between us [in school]." And he may be in between them for years to come.

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Doug Hutchison and Courtney Alexis Stodden: 35 Years

They may be B-list, but they still make this list. Doug Hutchison, a 51-year-old actor who has appeared in Lost, The Green Mile, and The X-Files, married 16-year-old aspiring country star Courtney Alexis Stodden in Las Vegas on May 20. "We're aware that our vast age difference is extremely controversial," the couple told E! Online through a spokeswoman. “But we're very much in love and want to get the message out there that true love can be ageless." Though Nevada requires marriage applicants to be 18 years of age, luckily for Stodden, a former Miss Teen USA contestant, she had her parents’ blessing. Stodden’s 47-year-old father, Alex, told RadarOnline.com that his new son-in-law, who is four years his senior, is “the nicest man I’ve ever met in my life… Every father can only pray to have such a man behind their daughter.” Her mother Krista added to RadarOnline.com, “We are totally supportive of this marriage.” She added that, "Courtney was a virgin when she married Doug. She is a good Christian girl." T.M.I., Mom.

Gaas / AP Photo

Woody Allen & Soon-Yi Previn: 35 Years Apart


As far as Hollywood love triangles go, it doesn't get much stranger than now-75-year-old Woody Allen's longtime relationship with Mia Farrow that led to an affair with her adopted daughter from a former marriage, then-21-year-old Soon-Yi Previn, and one of the craziest custody battles in celebrity history. Farrow discovered nude photos of Previn in Allen's apartment while she and Allen were still together, and five years later, Previn and Allen wed. When he finally opened up about the controversial relationship to Vanity Fair in 2005, Allen said it was "one of the truly lucky things that happened to me in my life." He added: "If somebody told me when I was younger, 'You're going to wind up married to a girl 35 years younger than you and a Korean, not in show business, not having any real interest in show business,' I would have said, 'You're completely crazy.' Because all the women that I went out with were basically my age. Two years younger. Ten years was the maximum. Now, here, it just works like magic. The very inequality of me being older and much more accomplished, much more experienced, takes away any real meaningful conflict. So when there's disagreement, it's never an adversarial thing. I don't ever feel that I'm with a hostile or threatening person. It's got a more paternal feeling to it. I love to do things to make her happy. She loves to do things to make me happy. It just works out great."

Katy Winn / AP Photo

Clint Eastwood & Dina Ruiz-Eastwood: 35 Years Apart


At 80 years old, Oscar-winning actor-director Clint Eastwood has had seven children by five women, only two of whom he's been married to. Eastwood met Dina Ruiz, his second and current wife, when the then-28-year-old local California anchorwoman interviewed the then-63-year-old star in 1992 about his Academy Award-winning film Unforgiven. Three years later, he surprised her with a private wedding ceremony at his Las Vegas home, and 8 1/2 months later, their daughter, Morgan, was born. So what won Eastwood over? "The big doe eyes. She's a very forthright kind of person. It's one of those things you can't put your finger on because it's pheromones or something. So we got married, and we had a child, and we're still together. Eleven years," he told Carmel magazine. And despite Ruiz-Eastwood being younger than Eastwood's eldest daughter, Kimber Tunis, and 35 years his junior, she says he's the one with the energy. "Being married to Clint is almost a full-time job, just trying to keep up with him," she told Carmel.

Evan Agostini / AP Photo

Calvin Klein & Nick Gruber: 47 Years Apart


In May 2010, then-67-year-old fashion legend Calvin Klein started showing up to events with then-20-year-old model and former porn star Nicholas Gruber. Rumors began flying about the twice-married designer and Gruber, who turned out to be a former Florida resident and alleged current student at Santa Rosa Junior College north of San Francisco, Gawker revealed in August. Since then the two have been spotted on trips to Miami and at a star-studded 21st birthday party Klein threw for Gruber in New York in January.