When the Geezer Gets the Girl: Nine Cradle-Robbing Celebrities

They say that love knows no bounds. According to these couples, it certainly doesn't discriminate on the basis of age. From Hugh Hefner's romp with the girls next door to Susan Sarandon's ongoing relationship with a man 12 years her junior, these celebrity power couples are proof that age really is just a number.

Hugh Hefner and…Everyone?
At the ripe age of 82, the king of the Playboy empire has reportedly ended his relationship with the trio of blondes known by television audiences as “The Girls Next Door.” After kissing 28 year-old Holly Madison, 35-year-old Bridget Marquardt, and 23 year-old Kendra Winkinson goodbye (as well as out of the Playboy Mansion and off their reality TV show), Hefner is on the prowl and rumored to be dating 19 year-old twins Karissa and Kristina Shannon who recently moved into the mansion themselves.



Woody Allen and Soon-Yi
The relationship that everyone thought would fail turns 11 this year. After marrying his adopted daughter, Soon-Yi Previn, a woman 35 years his junior, then 62-year-old Allen went on to direct 14 films including the recent hit "Vicky Cristina Barcelona." Soon-Yi isn't the first time Allen's robbed the cradle. Prior to leaving actress Mia Farrow for his adopted daughter, Allen had also dated Stacy Nelkin, an actress 24 years younger whom the film "Manhattan" is based on.




Michael Douglas and Catherine Zeta-Jones
What difference can a decade (or two) make? Not much according to Douglas. Meeting now wife, hottie Catherine Zeta-Jones, an actress 25 years younger, at the Deauville Film Festival, Douglas reportedly wooed her for over 9 months by phone before any physical sparks flew. "As soon as I met Catherine, I told her I wanted to have babies with her," Douglas told the Sunday Telegraph, "and the moment I found out she had the same birthday as me -- ta dah! Then, when I discovered she loved golf, I realized all my fantasies had come true."



Larry King and Shawn Southwick-King
For the 48-year-old wife of CNN staple Larry King, the sixth time's a charm. After being married to five women, the 74-year-old news anchor has settled down for the past 10 years with former singer and television host Shawn Southwick. Despite her five predecessors, Southwick-King is confident that she's the one, boasting at the couple's anniversary party last September that she's "the only [wife] to have lasted into the two digits," according to the New York Daily News.



Harrison Ford and Calista Flockhart
Sure, he's fought space creatures, outrun boulders, and run the country on the silver screen, but is he up to his greatest challenge yet -- managing a new marriage with a 23-year age gap? Reportedly engaged to former Ally McBeal star Calista Flockhart, the 66-year-old former Sexiest Man Alive will not only take on a booming Hollywood actress, he'll also take on her 7-year-old adopted son, Liam, as well.




Rod Stewart and Penny Lancaster-Stewart
Despite their 26 year age gap, 37-year-old former model Penny Lancaster-Stewart still answers the question “Do Ya Think I'm Sexy?” right every time. Marrying last summer on a yacht in Portofino, Italy, Lancaster-Stewart is Stewart's third wife and the mother of Stewart's sixth child. Despite having a new wife and six kids, the Rock n Roll Hall of Famer reports that he wants to produce an R&B album and keep performing until he's 70. At this rate, Penny may be the one struggling to keep up.



Robert Redford and Sibylle Szaggars
After dating for 12 years, the 71-year-old actor/director/political activist has plans to settle down with German artist Sibylle Szaggars, nevermind the 19-year age gap. Popping the question at his eco-friendly ranch in Sundance, Utah, Redford has stayed quiet about both the relationship and the upcoming nuptials, telling the press only, “Sibylle is my fiancee and that says everything, doesn't it?”



Robert De Niro and Grace Hightower
De Niro and Hightower are proof that love between the ages isn't easy. Marrying in 1997, the now 65-year-old actor and 55 year-old actually filed for divorce in 1999, then reconciled their relationship in 2000 before the procedure was complete. In 2004, they renewed their vows in front of an A-list celebrity crowd including Martin Scorsese, Meryl Streep, Ben Stiller, and Tom Brokaw. According to the New York Daily News, De Niro had two judges officiate, “so they can make sure this one sticks.”





Susan Sarandon and Tim Robbins
Men aren't the only ones seeking younger mates. 62-year-old Susan Sarandon and her 50 year-old longtime partner Tim Robbins have been going strong ever since meeting on the set of "Bull Durham" in 1988. Not one to let age get in the way of relationships (or anything else), Sarandon recently posed semi-nude for an upcoming book of Hollywood pinups photographs produced by artist Timothy White, telling reporters, "What a treat to play in the world of the beautiful, perfect pinup fantasy.”

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