Hollywood's May-December romances

Calvin Klein, 68-years-old, and model Nick Gruber, who is 48 years his junior.
Klein was previously married to Jayne Centre in the '60s and Kelly Rector in the '80s, but has admitted that he's had relationships with men and women. 

 

Mickey Rourke - Anastassija Makarenko
Mickey Rourke has already had the comeback of the century, being nominated for an Oscar and winning a Golden Globe for 'The Wrestler,' but the 57-year-old actor has nabbed an equally coveted trophy: a sexy young blonde. The reformed bad boy has been dating much-younger Russian-born model Anastassija Makarenko.

 

Madonna - Jesus Luz
When Madonna and her ten-years-younger husband, Guy Ritchie, called it quits in 2008, the eternally youthful material girl wasted no time rebounding with an even younger boy-toy. Madge started dating 23- year-old Brazilian model Jesus Luz in 2009, and the pair has been spotted all over the globe since.

Ick Factor: Jesus' mother is 14 years younger than Madonna.
 

Clint Eastwood - Dina Ruiz-Eastwood
Legendary Hollywood director Clint Eastwood met his wife, Dina Ruiz-Eastwood, while she was interviewing him in 1993. Despite the fact that Ruiz, a former reporter and news anchor, 44, is 35 years younger than Eastwood, the couple wed in 1996, and have a daughter together.
 

 

Linda Bollea - Charley Hill
Hulk Hogan's ex-wife, Linda Bollea, takes the cake as the cougar queen. Linda, 51, and her 21-year-old boyfriend Charley Hill, started dating when he was only 19! But the duo's matching platinum 'dos aren't the freakiest thing about this relationship ...

Ick Factor: The Hogan kids, Brooke and Nick, are 21 and 19, respectively. In fact, Charley is a former classmate of Brooke's

 

 

Hugh Jackman  &  Deborra-Lee Furness
Hugh Jackman has conquered the big screen, Broadway, and was named People's Sexiest Man Alive in 2008 -- so you'd think the Aussie actor would be with a new hot young starlet every week. Wrong. The 41-year-old hottie has been happily married to 55-year-old actress Deborra-Lee Furness since 1996, after the pair met on the set of the Australian TV series, 'Correlli.'

 

 

Woody Allen & Soon-Yi Previn

In 2005, the notoriously private Woody Allen finally discussed his scandalous marriage to Soon-Yi Previn. Despite never getting married, the now 74-year-old filmmaker and actress Mia Farrow were together for twelve years, had one biological child and adopted two children together, one of whom was Soon-Yi. The pair split in 1992 after Farrow discovered Allen, then 56, and Previn, then 22, were having an affair.

Despite a 35-year age difference, the couple have been together ever since, tying the knot in 1997.

 

 

 

Joan Collins & Percy Gibson
British actress and author Joan Collins got tongues wagging in 2001, when she started seeing then-35-year-old Percy Gibson, a theater company manager 32 years younger than her. The former 'Dyansty' star, now 76, made Gibson her fifth husband in 2002.

 

Canadian diva Celine Dion, 41, ended up marrying her much-older manager, Rene Angelil in 1994, after keeping their relationship secret for fear the public would deem it inappropriate. Rene is 26 years older than the superstar singer.
 

 

Donald Trump certainly has his fair share of ex-wives, but it seems he's struck gold with his youngest one yet, model Melania Trump, 39. The 63-year-old media mogul may have 24 years on his better half, but it seems Melania can hold her own, and has even perfected her hubby's famous pout.

 

But don't feel too bad for the Donald's ex Ivana -- she, too, found a younger match. Ivana, also a serial monogamist, found herself husband no. 4, Rossano Rubicondi, an Italian entrepreneur 24 years her junior. The couple, who dated for six years, got married in April, 2008, but divorced just seven months later.

The 61-year-old socialite has made no secret of her cougar tendencies: She starred in her own reality show called "Ivana Young Man" in 2006.
 

 

Italian businessman Flavio Briatore, 60, a notorious modelizer, dated supermodel Heidi Klum in 2003, and ended up getting her pregnant. However, the same day she announced she was expecting, photos of Briatore kissing another woman surfaced.

Klum, now 36, split with Briatore, and met hubby Seal while she was pregnant. Briatore went on to be linked to other younger women, notably model Emma Heming, who would later marry Bruce Willis

 

In 2004, at the age of 55, musician Billy Joel wed his third wife, Katie Lee, then 23-years-old.

Ick factor:At the time, Joel's daughter, Alexa Ray, from his marriage to supermodel Christie Brinkley, was a mere 5 years younger than his bride.

But in 2009, the couple split amid rumors that Lee had cheated with a man a bit closer to her age, Yigal Azrouel, a 36-year-old Israeli-born fashion designer.

 

 

Over the years, Cher's been linked to more Hollywood mainstays than anyone can keep track of, but one relationship that stands out from all the rest was her Bagel Boy phase.

In the 1980s, Cher dated a bevy of younger men, including Tom Cruise and Val Kilmer. But on her 40th birthday, Cher met 22-year-old bagel baker Rob Camilletti, with whom she ended up living for three years. The tabloids claimed the odd couple planned to marry, but no wedding ever took place.