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15 Hot Celebs With Much Older Sugar Daddies

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15 Hot Celebs With Much Older Sugar Daddies

For years and years, most marriages of the rich and famous are a bit like the couple from Beauty and the Beast, with the “beast” being loaded with riches, and the beauty loaded with assets. You get the point; the richest men have the most beautiful partners, and the age difference doesn’t seem to matter at all!

Women who want to live a good life with all the big homes, the jaw-dropping walk-in closets, the well-dressed help, and those gorgeous cars (along with all the plastic surgery that money can buy) more often than not choose partners who can provide them with their kind of a lifestyle. Not that we are saying that these marriages are not made in heaven – but perhaps these bonds are kept together by the accounting department up there.

Many of these women who chose older men as their daddies, uh, husbands were fairly rich in their own right. And we are assuming, for the sake of humanity, that at least some of these marriages are indeed based on love or at least mutual respect, considering many are successful! But you have to agree that some of these ladies really wanted the moolah, and the men really wanted to dangle their trophy wives on their aging arms.

These sugar daddies of Hollywood married their sugar babies, and while some of these marriages did end in divorces, a ton of alimony, and plenty of regret and public spats, many of them are going good and strong. Some, though, ended in tragic deaths. Food for thought, no? So here it goes, the 15 really hot celebs with much older “sugar daddy” husbands.

15. Alec Baldwin & Hilaria Thomas: Second Time’s A Charm

Alec Baldwin‘s first marriage (to Kim Basinger) did not work out for either of them. In fact, it provided plenty of fodder for the media to happily share with the public. Alec and Kim met in 1990 while filming The Marrying Man. Ironically, they married in 1993 and had a daughter in 1995. In 2000, it was all over and by 2002 they divorced. Supposedly, Alec tried to remain close to their daughter but, he said: “Kim managed to alienate my child from me very well.” After some seven years of trying to remain close to his daughter, he broke and left an angry voicemail message in response to another unanswered arranged call where he called his 11-year old daughter a “rude, thoughtless little pig.” He later revealed that by 2009 he was almost suicidal after the tape was leaked.

Alec finally met someone to heal his heart and in 2011, began dating Hilaria Thomas, a yoga instructor. They moved in with each other in August and became engaged in April 2012. They married in June the same year when Alec was 53 and Hilaria was 27! And now the couple have three children together.

14. Sylvester Stallone & Jennifer Flavin: When Love Transcends All Ages

Jennifer Flavin was born in California in a family of six siblings. Her father died when she was 11 years old, and so her mother brought up all seven children on her own. Flavin started modeling when she was 19, and in 1988, she met Sylvester Stallone at a Beverly Hills restaurant. Stallone married her nine years later, in 1997, and at the time, he was a ripe 51 while she was 29. They are still married and have three beautiful daughters, Sophia, Sistine, and Scarlet. When asked about his daughters, Sly says “I have to give Jennifer all the credit. I’m stunned that life has moved by so quickly, and my daughters turned out so wonderfully.” Sophia is a student at USC while Sistine is following her mother’s footsteps and becoming a  model. The youngest, Scarlet, 14, is as beautiful as her sister, as well as a talented athlete.

13. Hugh Hefner & Crystal Harris: A Marriage Written In Diamond Dust

Hugh Hefner married Crystal Harris on December 31, 2012, when he was 86 and she was 26 but the marriage was not without drama. Crystal Harris started dating Hefner in January 2009. This was after the Shannon Twins and after Hugh’s previous numero uno girlfriend Holly Madison. In 2010, the couple got engaged and Crystal was to become his third wife but five days before their planned wedding, Crystal broke off the engagement. However, in anticipation of their wedding, the July Playboy issue was out early, introducing Crystal as the new Mrs. Hefner on the cover. The newsstand magazines later carried a “Runaway Bride” sticker on the cover.

Crystal later admitted to having second thoughts about the marriage which is why she called it off. That didn’t stop her from going back to Hugh, or him from taking her back! So finally on December 31, 2012, Harris and Hefner married at the Playboy Mansion in a small private ceremony. In 2016 Crystal also announced that she had Lyme disease and what is known as “breast implant illness” in which she experiences brain fog and chronic fatigue caused by her ruptured implants. She had her ruptured implants removed immediately and got better (and smaller!) in no time.

12. Rod Stewart & Penny Lancaster: A Penny For Your Thoughts

Rod Stewart married Rachel Hunter in 1990 when he was 45 and she was 20 and after 16 years of marriage, they divorced in 2006. They have two children. Rod Stewart swore that Rachel had broken his heart and after two divorces he joked, “I’m just going to find a woman I don’t like and give her a house!” The next year, “heart-broken” Rod went ahead and married model Penny Lancaster when he was 62 and she was 35. They are still married today but, well, it’s only been seven years!

Penny stands tall at 6’1″ and is a certified fitness trainer. Fun fact, she suffers from a sweating condition called hyperhidrosis where the person sweats too much. This disease is often called the silent handicap for it comes with various physical, mental, and lifestyle burdens! A marriage to Rod Stewart takes away some of that pain, we hope!

11. Elizabeth Taylor & Mike Todd: The Tragedy Of True Soulmates

Elizabeth Taylor was no stranger to marriage, though hers was not a search of lust, but for love. All her life, Taylor’s personal life, and her eight marriages, drew a large amount of media attention and flak. At 18, Taylor married Conrad “Nicky” Hilton, Jr., heir to the Hilton Hotels chain, but he turned out to be abusive and a heavy drinker. Eight months later, they divorced. Then she married British actor Michael Wilding, 20 years older than her but two kids and five years later, this marriage was over too. In 1957, when Taylor was 25 and showman Mike Todd was 50, they got married. They had a daughter, Liza Todd, and remained married until he died in 1958. This was the only marriage of Taylor’s that didn’t end in divorce. Sadly, Todd died in a plane crash that left Taylor devastated. She called him one of the three loves her life, along with Richard Burton (husband number 5 and 6 as well) and jewelry!

10. Anna Nicole Smith & J. Howard Marshall II: Gold Digger! Who, Me?

The tale of Anna Nicole Smith is no fairy tale. She married a rather ailing prince, business magnate J. Howard Marshall II in 1994, when she was 26 and he was 89. The couple, if you could call them that, were together for just little over a year, 13 months to be precise, before this octogenarian (or nonagenarian) finally passed away in 1995. The media was vicious when it labeled her as a money-minded gold digger who divorced her first husband just to marry Marshall for his money. Allegedly, she never lived with him, never had sex with him, and only kissed him on the mouth no more than ten times! Once her husband died, Smith began a lengthy legal battle over a share of his estate.

Sometime later, she married her longtime attorney Howard K. Stern and had a baby daughter – of whom many tried to claim paternity. A few months after her daughter’s birth, Anna Nicole was found dead in her room, by an OD, after the suicide of her son left her depressed. Not the ending she or anyone else had hoped for!

9. Billy Joel & Katie Lee: She’s Always A Woman To Me

So, we all know Katie Lee as a cookbook author, food critic, and chef, and stars in her own series Beach Bites with Katie Lee and The Kitchen. And while she used to listen to Fleetwood Mac and Rolling Stones because her mum played them, she only listened to Billy’s songs once she met him at a hotel. The two connected, dated, and finally got married in 2004, with Billy’s daughter Alexa Ray Joel serving as the maid of honor. At the time, Katie was 23 while Billy was 55. Incidentally, Alexa was 18 at the time. By 2010, the age difference between Katie and Billy caught up with them and they divorced, issueless and amicably with a hefty settlement for Katie. Katie also attributes her career success to Billy, partly, saying, “I’m the first person to say having that last name (Joel) helped me get a foot in the door…” Billy remarried in 2015 at age 67, this time to Alexis Roderick (aged 33 at the time), and they have a daughter too. Sugar daddies never change!

8. Humphrey Bogart & Lauren Bacall: A Love So “Openly” Dedicated 

Sometimes, marriages are really based on a love so strong, that age is simply just a number. And such was the romance between Humphrey Bogart and a much younger Lauren Bacall. After Casablanca’s unmitigated success, an Ernst Hemingway novel was fashioned into a movie called To Have and Have Not. The director Howard Hawks liked a young model on an Esquire cover and so flew her over – Lauren Bacall then got her first movie role opposite the actor she found “unsexy.” During the shoot, the actors naturally fell in love. At the time, Bogart was 25 years older, married, and a heavy drinker. What was Bacall thinking then? Nonetheless, their affair continued and finally, Bogart divorced his wife and married Bacall when she was 25 and he was 40. For the next decade, the couple remained happily married, with two kids and more movies. She accepted his mistress and he accepted her interest in Frank Sinatra once he was diagnosed with esophageal cancer. Total acceptance does a happy marriage make!

7. Larry King & Shawn Southwick: The Kingly Marry-Go-Round

Larry King is simply no stranger to getting hitched considering he has been married a total of eight times to seven different women. His last marriage is also his longest lasting one. This was when he married Shawn Southwick in 1997 when he was 64 and she was 38. They are still married today. Perhaps she was good for his heart, considering he married this TV host, in a hospital room three days before King underwent heart surgery to clear a clogged blood vessel. Despite a weak heart, the couple went on to have two children.

His love of marriage started with his high school sweetheart. After an annulment, another brief marriage happened, that resulted in a son, and then came a Playboy Bunny wife. Then another wife who dumped him, upon which he remarried the Playboy Bunny Alene, with whom he had a daughter. After yet another divorce came a math teacher wife, and then a businesswoman wife. Finally, he married his current wife Shawn in 1997. The marriage had a troubled path and they did file for divorce. Luckily, they reconciled.

6. Harrison Ford & Calista Flockhart: A Love So Strong

So when Harrison Ford was a rocking 60 years old, he began dating Ally McBeal, errr, we mean Calista Flockhart in 2002, when she was 38. And some eight years later, when Ford was 68 and Calista 46, they got hitched and they have been co-parenting her adopted son, Liam, ever since. A 22-year-old gap between them doesn’t seem to hold a candle to the flame that is there in their marriage! Said the actress, “Harrison and I laugh a lot, and humor is everything to me. The truth is, I sometimes feel very much older than Harrison… In fact, I keep forgetting that he’s 22 years older than me. The so-called age gap has never been a factor in our relationship at all. I love the way he looks first thing in the morning. It’s not handsome, it’s cuter. He looks like a little boy…” So this one is definitely for keeps!

5. John & Bo Derek: 22 Years Of A Rock Solid Marriage

When Mary Cathleen Collins was discovered by the much older John Derek, he couldn’t keep his eyes (or hands) off her! They got romantically involved when she was just 16, and he was way older at 46. He divorced his wife Linda Evans and to avoid the charge of statutory rape, they fled to Germany and came back only once she was legal. In 1976, they married – she was 20, he was 50! And now, she went by the name we all know her as, Bo Derek.

Despite her career going nowhere with the films that John Derek made, Bo remained a steadfast wife to him. The marriage lasted all the way until John’s death and by all accounts, it was a fairly pleasant one. John Derek passed away in 1998 and the couple had stayed married for 22 years. Following John’s death, Bo is now involved with another John – actor John Corbett. Interestingly, before Bo, John Derek had been married three times already, and three times divorced. Bo made this marriage last.

4. Sophia Loren and Carlo Ponti: An Unshakeable Love

The beautiful Sophia Loren officially married film producer Carlo Ponti in 1966. She was 32 to his 54. But this was not their first rodeo! In fact, they had first met when Sophia was just 15 and Ponti was 37. And in fact, they had actually had their first wedding 11 years before in 1957, but at the time, Ponti was still married to his first wife, Giuliana. Since Italy did not recognize divorce, Loren and Ponti had their marriage annulled. In 1965, Ponti obtained a divorce from his wife Giuliana in France and then Loren and Ponti applied to become French citizens. Once their application was accepted, they married and then went on to have two children.

Ponti and Loren remained very much married and in love, till death did them part. Ponti died in 2007 of pulmonary complications. When asked if she could ever marry again, Loren said, “No, never again. It would be impossible to love anyone else.”

3. Shania Twain & Robert Lange: That Don’t Impress Me Much

Shania Twain married music producer Robert Lange in 1993 when she was all of 28 and he was 44, and they had a son in 2001. The fact that he was married to a beautiful woman, a great singer, and the mother of his child wasn’t enough for him it seems. The couple divorced in 2010 after it was found out that Lange had an affair. And not just with anyone, but with Twain’s best friend! To top off her troubles, her voice was waning. Specialists discovered lesions on her vocal cords and diagnosed her with dysphonia, which she attributes to Lyme Disease. Luckily, all this was treatable with careful rehabilitation and Shania has been able to make a decent comeback.

Shania broke ties with her husband and her best friend but through this, her former friend’s ex-husband, Frédéric Thiébaud, stayed by her side and the pair eventually married in 2011. As for Lange, his affair didn’t impress Shania much!

2. Johnny Depp & Amber Heard: The Bigger They Are…

So Johnny Depp was happily living with his longtime partner Vanessa Paradis when he met Amber Heard during the shooting of their film The Rum Diary. Four years later, Johnny had moved on from Vanessa to Amber, and they married in 2015 after living together for a while, while she was 29 and he was 52. All seemed well and good and despite the Australian dog scandal, the couple seemed in love. That is, until Johnny’s long-ailing mother passed away, and two days later, Amber filed for divorce. Five days later, she filed a restraining order on him, citing domestic abuse.

While we all know how that ship sunk, this was one very public divorce with everything being “leaked” to the media rather conveniently. The truth of the marriage will forever stay with the couple, but Johnny settled the matter for some $7 million, and the marriage ended in a rather public debacle in 2017.

1. Tom Cruise & Katie Holmes: You Can’t Have Your Cake And Eat It Too, Tom!

Tom Cruise has a bit of a mean streak of dumping one wife for another so quickly, that he makes heads spin. When his eyes landed on the stunning Nicole Kidman, he dumped his then wife Mimi Rogers (older than him by six years) and married Kidman, who was five years younger. In 2001, he divorced Kidman and left her shattered, and then dated Penelope Cruz.

Finally, Tom Cruise met Katie Holmes, and they became Hollywood’s favorite couple, often dubbed TomKat. After having daughter Suri in April 2006, Tom and Katie got married in 2006 – while she was 28 and he was 42. A few years of wedded bliss went by before Katie surprised Tom with a divorce filing in 2012, fearing Tom and his rigid Scientology beliefs. Tom settled the divorce for an undisclosed sum and Katie got custody of Suri.

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