Most Bizarre Celebrity Prenups in History

Celebrity divorces can sure be expensive, so it never hurts to get a prenup first — however unusual they may be.

When you have as much money as Jennifer Aniston or Britney Spears, it’s only natural that you’d want to protect your assets in the oh-so-extremely-unlikely event that you fall out of love with your as-equally famous partner.

Indeed, prenuptial agreements aren’t just for the rich and famous anymore, with more millennials signing on the dotted line. But it’s these big-league contracts — including clauses that address weight gain, infidelity and even alone time — that are certainly the most interesting. After all, when you’re this rich, it’s pretty much a guarantee you need one.

Britney Spears and Kevin Federline

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Kevin Federline was pretty much famous for being the spouse of Britney Spears and little else. In fact, his lack of talent made for tons of fun on late-night comedy shows, but K-Fed may have had the last laugh when he walked away with a million bucks of Brit-Brit’s cashola in their 2006 divorce proceedings.

However, despite his windfall, Federline could have left the marriage with far more money had Spears not made him sign a prenup.

Beyonce and Jay-Z

Jeff Daly / Invision for Parkwood Entertainment / AP Images

There’s almost no one more successful than Jay-Z — except for his wife, Beyonce. Absolutely no one is more successful than Queen Bey. And 2014 reports show that Bey will actually get even richer in the event of a divorce.

The couple’s prenup stipulates that the subway-line-named rapper will have to fork over $1 million for every year they were married after the first two years. And she’ll get an additional $5 million for each of the couple’s three children — reported Women’s Health.

Best hang in there, Jay. But one can only imagine the breakup albums that would result!

Tom Cruise and Katie Holmes

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Because Scientologists don’t like you to talk about them publicly, it makes sense that Tom Cruise’s lawyers made one-time spouse Katie Holmes an offer she couldn’t — but maybe should have — refused. As part of their courtship, the “Mission Impossible” superstar’s people offered Holmes $3 million a year up to $33 million for each year that she is married to Cruise.

The marriage lasted less than a decade, and Holmes has been cagey about discussing the marriage — almost certainly due to an NDA gag order. But that hasn’t stopped the rumor mill from sprouting myths such as that Cruise’s lawyers “forbid” her to date for five years as part of the divorce settlement.

Michael Douglas and Catherine Zeta-Jones

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Many thought the quarter-century age difference would end their marriage before it began, but here we are 18 years into the Douglas and Zeta-Jones show, with the couple still going strong at ages 74 and 49, respectively. Get ready for this: So, in addition to her acting work, Zeta-Jones actually “earns” $2.8 million per year just for being married to Douglas. This was part of the couple’s prenup, which also includes an additional $5 million “bonus” for the Welsh actress if Gordon Gekko ever gets his, uh, lizard on elsewhere.

By our calculations, that means the Oscar-winning actress has accrued more than $50 million solely for the Herculean accomplishment of staying married to Hollywood’s most infamous former philanderer. Who says love is dead?

Gisele and Tom Brady

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The latest couple to announce a divorce is Gisele and Tom Brady. Since the two are super wealthy on their own, it’s no surprise that they had an iron-clad prenup. After all, she’s worth about $400 million to his $333 million.

Luckily for them, it’ll make their separation somewhat easy. The key thing they’ll have to divide is the real estate they acquired during their 12-year marriage, and only time will tell how that goes.

Kanye West and Kim Kardashian

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Ah, to be a Kardashian. Not only do you get money just for putting your name on a tissue box, but you also stand to make out like gangbusters in the event things don’t work out at home. Thanks to Kim and Kanye’s prenuptial agreement, she got $1 million, capped at $10 million, for every year she was married to him.

Not only that, a divorce meant she got the title of their Bel-Air mansion as well as all the jewelry and gifts that he ever gave her — which was a lot.

Liz Taylor and Larry Fortensky

Richard Drew / AP Photo

The late great Liz Taylor was married eight — count ’em, eight — times and twice to Richard Burton alone. Her final husband was Larry Fortensky, a Hollywood area construction worker, whom Taylor is said to have met in the Betty Ford Center for alcoholic rehabilitation in 1988. Despite his being 20 years her junior, Taylor swooned for the younger man, but not before getting her lawyers involved.

Their prenup outlined that if the couple remained married for at least five years, Fortensky was promised $1 million as a “bonus.” However, the “Cleopatra” star pulled the cord on the union within one month of that deadline, thus depriving Fortensky of the payday.

Jennifer Aniston and Justin Theroux

Evan Agostini / Invision / AP

Poor Jen. All her money, fame and charm can’t keep her marriages intact. Jen’s most recent former spouse is actor/writer Justin Theroux (of “The Leftovers”), and when the couple split up last year, the celebri-verse couldn’t wait to speculate on how much “Friends” money Theroux might net.

But Us Weekly reported that “a source” said Jen had an “ironclad” prenup when the couple wed in 2015 to keep her substantial fortune safe.

Justin Timberlake and Jessica Biel

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Justin Timberlake is a heartthrob the world over, so it’s little wonder his actress wife Jessica Biel wanted to ensure that it would be in the former boy band mainstay’s interests to stay faithful.

The New York Daily News reported that, if the “Can’t Stop the Feeling!” singer ever steps out on his missus, she’s guaranteed a half-million dollars.

“Cry Me a River,” Timbo!

Tiger Woods and Elin Nordegren

David J. Phillip / AP Photo

The world’s most accomplished golfer is also one of the planet’s most notorious philanderers, so it made sense that when Elin Nordegren said “I do” in 2004, it came with a prenup that stipulated she would also say “I’ll take that!” if Woods cheated.

Well, fast-forward to the end of the aughts, and Woods once again got caught with his hand in the cookie jar. People reported that Nordegren was able to renegotiate the terms of their prenup, and she supposedly exited stage left with $700 million of his golf fortune.

Mark Zuckerberg and Priscilla Chan

Manuel Balce Ceneta / AP Photo

The Facebook founder, CEO and confuser of elderly senators who don’t understand how social media works is doing rather well, with a net worth north of $68 billion, making him one of the world’s wealthiest individuals.

But he and wife Priscilla Chan have a most unusual — one might even say charming — agreement signed before their big day that says Chan gets “100 minutes of alone time” and one date night per week with her hubs, during which time neither of them is allowed to look at, you guessed it, Facebook.

Jessica Simpson and Tony Romo

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File this under bizarre: Former Dallas Cowboys quarterback Tony Romo wouldn’t marry Jessica Simpson without a prenup stating that the reality star would have to fork over $500,000 for every pound she gained over a weight of 135 pounds.

Hmmm … it’s not too surprising that their marriage plans fell apart.

Nicole Kidman and Keith Urban

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Nicole Kidman has been through the marriage wringer before with Tom Cruise — there he is again!) So, when the Australian actress linked up with New Zealand singer Keith Urban in 2006, they worked out a contract together with a clause that Urban will “earn” $640,000 per year of marriage, according to MyWedding.com.

But because Urban once struggled with cocaine addiction, he won’t get a penny should he return to the nose candy habit.

Steven Spielberg and Amy Irving

AP Photo

A word to the wise: Don’t think that a cocktail napkin will hold up as a “legal document” in court. Hollywood kingpin Steven Spielberg learned this the hard way when first wife Amy Irving sued him for divorce after he began spending a bit too much time with his “Temple of Doom” leading lady, Kate Capshaw.

The Weinberger Divorce & Family Law Group (oh, you’ve heard of them!) wrote that Irving had their prenuptial agreement, jotted down on said cocktail napkin, tossed out in court as invalid, and a judge ruled she was entitled to half of Spielberg’s then-fortune of $200 million (it was the ’80s, so he wasn’t yet a billionaire).

Khloe Kardashian and Lamar Odom

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The Kardashian name isn’t just one of the most recognizable in American popular culture, it’s also a brand. Little surprise then that Khloe Kardashian, who reportedly earned $40 million in 2017 alone, made sure to have an airtight prenup with husband Lamar Odom.

The pair were married in 2009 after only knowing one another for a month, but the marriage lasted only a few years. Little wonder the reality TV darling would elect to protect her earnings.

Brad Pitt and Angelina Jolie

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If you’ve seen “By the Sea,” the film Angelina Jolie directed in 2015 starring herself and then-husband Brad Pitt, it’s somewhat easy to see why they split up not long thereafter. What’s difficult to understand is who got what house in which country, as the couple bought three together during their marriage.

Their prenuptial supposedly spelled out how their fortune would be divided, but it didn’t stipulate how custody of their many children would play out. And cue the lawyers.

Charlie Sheen and Brooke Mueller

Kevork Djansezian / AP Photo

Ah, Charlie Sheen. Sex addiction. Bipolarity. “Winning.” But thanks to the prenup he worked out with third wife Brooke Mueller in 2011, he stood to “lose” quite a lot. Gawker reported that not only would Mueller receive $300,000 per year of marriage, they also each signed away their right to sue to get the other’s earnings in the event of divorce.

Good thing they worked that out beforehand, as the marriage lasted just under three years.

Gwyneth Paltrow and Brad Falchuk

Chris Pizzello / Invision / AP

We all remember when Gwyneth Paltrow “consciously uncoupled” from Coldplay frontman Chris Martin, but it wasn’t long before she paired up again, this time with producer Brad Falchuk.

Because both parties had been married previously, it’s little wonder they negotiated a prenuptial contract prior to tying the knot last September.

Michael Jordan and Yvette Prieto

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Michael Jordan was the undisputed king of the basketball court (although Larry Bird might disagree), but even he couldn’t outmaneuver ex-wife Juanita from taking $168 million of his fortune in a divorce settlement. Apparently, he learned his lesson, as Jordan and subsequent wife Yvette Prieto put it down in writing prior to getting hitched that they would walk away with their pre-marriage fortunes intact if the relationship turned sour.

However, according to UrbanDaily, Prieto is “entitled” to a million dollars per year of wedded bliss, and $5 million per year after they hit the decade mark in 2023. Good luck!

Victoria Principal and Harry Glassman

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Even with a prenup in place, the get-out-of-marital-jail card can still be rather pricey.

Just ask former “Dallas” actress Victoria Principal, who, despite what she thought was an airtight prenup, still wound up paying plastic surgeon Harry Glassman $25 million in their divorce proceedings. The couple split in 2006 after 21 years of marriage.

Chris Rock and Malaak Compton-Rock

Matt Sayles / AP Photo

Chris Rock has made his serial infidelities and ensuing divorce a centerpiece of his most recent standup special, “Tambourine,” wherein he also discusses life as a newly single dad and having the court send someone to his house to make sure it’s “livable” for his children. (“What have you heard about me?” Rock says he wanted to tell the judge in the hilarious special.)

However, Rock’s divorce might have been a lot less painful had he not paid attention to his prenup. According to Page Six, Rock and former wife Malaak Compton-Rock signed a prenup when they married in the mid-90s, but it expired juuuuuust before he filed for divorce in 2015. Accordingly, Compton-Rock sued her famous spouse for a good portion of his fortune.

It hurt his piggy bank for sure, but it made for some outstanding comedy material.

Ice T and Coco Austin

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They may be one of the most famous celeb couples out there, but word on the street is that if things ever go south for Ice T and Coco, things could get really ugly in a very unusual way. According to a source cited on Ranker, the couple’s prenup states that in the event of a separation, the rapper would like his wife to, uh, “hand back” the breast implants and butt lift he paid for.

How exactly this reverse-plastic surgery would occur is not spelled out, but feel free to speculate.

Charlie Sheen and Denise Richards

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We reported before on Charlie Sheen’s prenup with third wife Brook Mueller, and it seems the most notorious member of the Estevez clan might have learned a thing or two from his earlier marriage to “Wild Things” and “Starship Troopers” star Denise Richards.

The pair met while filming the 2001 comedy “Good Advice” and wed the following year. Their union was dissolved in 2006, and it’s likely Sheen had to pay out handsomely given that their prenup stipulated Richards would leave the marriage with cold hard cashola if the “Wall Street” star ever cheated — which he almost certainly did.

Roseanne Barr and Tom Arnold

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Long before Roseanne Barr’s Twitter tantrum got her fired from her self-titled show — since retitled “The Connors” — she and “Roseanne” writer Tom Arnold tied the knot in 1990. Their divorce was ugly, and Arnold told me in 2016 that he came home one day to find his clothes tossed in their pool and the ice trays even removed from the freezer (a gag he suggested be added to the script for “True Lies”).

During the courtship, Barr’s lawyers were said to have requested a prenup with Arnold, but he refused. Lo and behold, when the pair split, things got ugly, with one stipulation of their divorce being that neither of the former spouses could make public jokes about the other’s genitalia. (That happens to the rest of us so often.)

Somehow, despite the acrimony, Arnold was there for his ex-wife’s Comedy Central Roast in 2012, and there’s video out there of her thanking him backstage for even showing up.

Halle Berry and Oliver Martinez

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What a great-looking couple! Alas, things didn’t last long for the Oscar winner and her French hubby, and they split up after less than four years of wedded bliss.

RadarOnline.com reports that their pre-wedding agreement set down that Martinez wouldn’t get any divorce money, but the question is did the divorce harm his career as well?

Martinez has only one acting credit to his IMDB resume since their 2016 separation, so you do the math.

Hugh Hefner and Crystal Harris

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The Playboy founder and publisher married for the third and final time in 2012 to model Crystal Harris, and before they walked down the aisle (bunny ears on their heads?) Hefner had Harris — 60 years his junior — signed an agreement that she wouldn’t be entitled to any of Hef’s estimated $200 million fortune if the marriage didn’t work out, AND that she would have to move out of the Playboy Mansion to boot!

Alas, Hef died in 2017 at the age of 91, so it’s possible her lawyers have tried to get a piece of the pie in the years since.

Jennifer Lopez and Ben Affleck

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Remember “Gigli,” the notorious box-office bomb that not only stalled Ben Affleck’s acting career for a while (honestly, who would have thought he’d turn out to be one of our best contemporary directors????), it also spelled the end of his relationship to co-star Jennifer Lopez.

The duo was working out the terms of their prenuptial agreement at the time “Gigli” became the stuff of late-night joke legend, and soon after, they called off the engagement entirely. RadarOnline.com says that their agreement would have given JLo half of Affleck’s earnings if he ever cheated. Affleck, meanwhile, wanted a cool 5 mil just for saying yes at the altar, plus a clause in their prenup stipulating sex at least four times a week!

Stars can be so demanding.

George Clooney and Amal Alamuddin

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Hollywood’s most eligible bachelor finally tied the knot with lawyer-activist Amal Alamuddin in 2014, thereby putting an end to decades of some of the most high-profile dating on the planet. The Oscar-winning actor and director is reportedly worth close to a quarter-billion dollars, and Alamuddin is promised a nice take-home if things don’t work out for the pair.

C’mon, George, prove the doubters wrong!

Jack Welch and Jane Beasley

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Financial wizard Jack Welch found out the hard way that even though you’re used to making millions of dollars, sometimes that wisdom doesn’t translate into protecting your money in case of divorce. MyWedding.com reports that Welch, the onetime head of megacorporation General Electric, didn’t pay close enough attention to the prenup he signed with wife Jane Beasley, as their agreement had a “sunset clause” guaranteeing her a ka-ching at the divorce table if the marriage dissolved after 10 years. Beasley is said to have then sued her wealthy husband for $150 million.

Let’s hope Welch made better decisions when it came to GE’s stock.

Jackie Kennedy Onassis and Aristotle Onassis

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Jackie O. went from being the world’s most famous widow to a tabloid darling thanks to her second marriage to Greek tycoon Aristotle Onassis in 1968, but that union was put to the ultimate test in 1972 when Onassis, as the story goes, was secretly behind an embarrassingly weird plot that resulted in Jackie’s nude sunbathing photos being sold to Hustler publisher Larry Flynt.

It gets even stranger still, as Onassis is said to have gone right to New York super-fixer Roy Cohn to get him out of the marriage to Jackie, but that would have cost him several million bucks thanks to their prenup.

Onassis died in 1975, and his famous widow said farewell to marriage for good at that point.

Ted Turner and Jane Fonda

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The Atlanta-based media baron married the most notorious member of the Clan Fonda in 1991, and rumors swirled early on that Jane was unhappy to move to the Deep South to be with her husband. The New York Post reported in 2000 that Fonda signed an agreement before their wedding that guaranteed her some of Turner’s massive fortune, but “only” $10 million of it.

Fonda put her acting career on hold entirely when she married Turner, and even after the couple divorced in 2001, she wouldn’t be in another film for four more years.

Brooke Shields and Andre Agassi

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Actress Brooke Shields said “I do” to tennis legend Andre Agassi in 1997, but their union was annulled only two years later.

The terms of their prenuptial accord were never disclosed publicly, but one website posited that under the terms of their separation, the pair would have been required to split assets worth a reported $130 million, including two homes in Las Vegas and Los Angeles.

William Cash and Ilaria Bulgari

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British journalist and author William Cash has had a run of hard luck in the nuptials department, most notoriously when he married Italian jewelry heiress Ilaria Bulgari in 2003. Cash went on to detail the specifics of the prenup in a recent essay for the Daily Mail, in which he said the wedding ceremony itself was purposely postponed while Bulgari’s attorneys worked on the legalese of their accord. Cash said that the Catholic priests marrying the couple took a “dim view” of such a document, but he agreed anyway.

Flash forward a spell, and Cash’s wife was busy auctioning off all of their possessions, including the marital bed! In his essay, Cash stated he had long since stopped communicating with Bulgari at that point, communicating with her only through her attorneys—as per her wishes

Melanie Griffith and Don Johnson

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This couple’s whirlwind romance went on for many years, and they actually began dating when Griffith was just 14 and Johnson 22 (ew!). The pair first wed in 1976, divorced almost immediately, and then re-tied the knot again in 1989. The pair split for good in 1996, but not before Griffith gave birth to Dakota Johnson, the star of those oh-so-quality “Fifty Shades” flicks.

According to Us Weekly, Griffith had a great deal to say about prenuptial agreements in the wake of her two failed marriages to Johnson (to say nothing of two additional divorces).

“Don’t get married,” was her response to a query about marriage in general, and prenuptial agreements in particular, with the “Working Girl” actress adding, “You either go through the whole [expletive] of a prenuptial, or if you want to get divorced and you don’t have a prenuptial, then you wish you had.”

Sharon Stone & Phil Bronstein

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Sharon Stone of “Basic Instinct” infamy walked down the aisle with San Francisco Chronicle editor Phil Bronstein in 1998, and all seemed to be going swimmingly — until it wasn’t.

The pair made an about-face on their union in 2004, and E! Online reported at the time things hit the rocks that Bronstein was trying to sue the Oscar-nominated actress for child support, even though their prenup supposedly forbade him from doing precisely that.

Watch out for that icepick, dude!

Joan Collins and Peter Holm

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Joan Collins didn’t enjoy quite the “dynasty” of wedded bliss she might have been hoping for when she put a ring on the finger of Swedish pop star Peter Holm in 1985.

And cue what the L.A. Times said was four and a half hours of “bargaining” to iron out who would get what in their 1987 dissolution of marriage. Holm sought $80,000 per month in spousal support but ultimately settled for $1 million. A judge ruled that Collins’ prenup with Holm limited him to just 20 percent of Collins’ earnings during those 13 long months they were actually wed.

Kandi Burruss & Todd Tucker

@MadameNoire / Twitter

Musician Kandi Burruss and somewhat-less-famous husband Todd Tucker married in 2014 and appear to be still growing strong as a couple.

Could it be because Tucker was so convinced Burruss was “the one” that he agreed to a prenup with almost no other questions asked, according to BlackAmericaWeb.

Gabrielle Union and Dwyane Wade

Joel Auerbach / AP Photo

NBA great Dwyane Wade is a lucky man indeed, having settled down with the beautiful Gabrielle Union in 2014 after a somewhat tempestuous courtship.

Since they’d already been through the ringer prior to exchanging vows, Union asked that her new hubs sign on the dotted line, telling Us Weekly, “I have my own wagon and star,” and thus didn’t need to ride the basketball player’s fiscal coattails in the event of divorce.

Janet Jackson & Rene Elizondo Jr.

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You have to keep on the pretty straight and narrow to be “the normal one” in the Jackson family, but when it comes to love, marriage and divorce in that musical family, Janet seems to have done things the least weird way.

In 1991 she married Rene Elizondo Jr., who would direct many of her music videos in the ensuing decade. But come the new millennium, it was splitsville for the high-profile item, and Elizondo subsequently sued Jackson for spousal support, claiming he felt pressured to sign a prenup with her nine years earlier. Elizondo won $10 million in cash in the end.

Guess he wasn’t cut out for “rhythm nation” after all.