Relationships can be trying enough sometimes for us regular folk. For celebrities, those challenges are amplified ten-fold as things like work schedules and the scrutiny of life in the public eye can strain even the strongest of couplings. Still, no one understands the life of a celebrity more than another celebrity, so it stands to reason that another person in the public eye can make the best, most relateable partners.
This bears keeping in mind as you read this list, where you will see plenty of couples who share little in common beyond their respective celebrity statuses. While most of these couples have since seen their nuptials come to an end, some continue to thrive in spite of a partnership that initially prompted a widespread public incredulity.
In certain situations, love is blind and one’s soul mate may not appear to make sense at first blush. Mary-Kate Olsen is still going strong with Olivier Sarkozy, the brother of former French president Nicolas Sarkozy, despite an 18-year age gap. Under other circumstances, stars may need to hit a pothole along the road to finding Mr. or Ms. Right. Ashton Kutcher and Mila Kunis appear well on their way to happiness together, but they had to get past respective relationships with Demi Moore and Macauley Culkin in order to get there.
Indeed, these strange pairings show that love conquers all. Well, sometimes anyway. Other times, a coupling that looks doomed on the surface soon becomes just that. Here are the 10 weirdest celebrity marriages:
10) Harrison Ford / Calista Flockhart
The marriage of Harrison Ford and Calista Flockhart has been so stable and strong over its five-year duration, it’s easy to forget how odd their pairing seemed when they first went public with their relationship 13 years ago. There was the 22-year age gap between the two and the strange contrast of the action hero movie star paired with a ditzy, quirky TV lead. But sure enough, Han Solo did end up with Ally McBeal and they have quietly thrived outside of the public eye ever since. Most recently, Flockhart was by Ford’s side day and night as he recovered from a plane crash in March.
9) Isla Fisher / Sacha Baron Cohen
In all likelihood, Sacha Baron Cohen was going to end up on this list with just about anyone he wed, as it isn’t easy to picture the deranged comedic creator of Borat, Bruno and Ali G being married at all. Good thing he married Isla Fisher, who boasts a naturally sweet demeanor but has revealed a bit of a quirky side to her personality through film roles like the obsessive Gloria in Wedding Crashers and the defiantly unfaithful Myrtle in The Great Gatsby. Still, the duo has made it work through five years of marriage and three children.
8) Mariah Carey / Nick Cannon
The 10-year age difference between the RnB diva superstar and the multi-faceted rapper, actor and comedian somehow always seemed larger than it was. When Mariah Carey and Nick Cannon were married in 2008, there was an evident contrast in terms of level of accomplishment between the iconic Carey and the relatively anonymous Cannon, who had largely been connected to Nickelodeon. It’s no wonder, then, that the pair announced their divorce in early 2014 after six years of marriage.
7) David Cross / Amber Tamblyn
One of the lesser known couples on the list, but yes, Arrested Development‘s Tobias Fünke is married to Joan of Arcadia. Some 19 years separate comedian David Cross and actress Amber Tamblyn, who met on the set of IFC sitcom The Increasingly Poor Decisions of Todd Margaret. Married since 2012, the two have set out on fairly divergent careers. Cross exists in a weird space between children’s movies (Alvin and the Chipmunks, Kung Fu Panda) and indie flicks (Kill Your Darlings, Obvious Child) mixed with a Pitch Perfect 2 cameo, while Tamblyn has traipsed between horror fare (The Ring, The Grudge) and the Sisterhood of the Traveling Pants film series.
6) Demi Moore / Ashton Kutcher
It takes a truly weird relationship to keep making headlines four years after its conclusion. Demi Moore and Ashton Kutcher have the 16-year age difference, but it is the details surrounding their messy split in late 2011 that has kept the pairing in the news of late. Moore’s daughter, Rumer Willis, recently opened up about the strangeness of seeing her mom wind up with her teenaged crush and – more maliciously – Scott Eastwood recently let slip on live TV about Kutcher cheating on Moore prior to their split.
5) Sean Penn / Madonna
Imagine if the Sean Penn and Madonna marriage, which lasted from 1985 to 1989, had taken place in the social media era. Surely, the forces of personality that were the Material Girl and the crazed Penn would have done their share of trending as a must-watch power couple. And that’s putting aside the tumultuous nature of their marriage, which included Penn shooting at paparazzi and Madonna’s constant head-turning public appearances. On a much darker note, there was the alleged incident when Penn suspected Madge of infidelity and tied her to a chair for hours of physical and psychological torture.
4) Christina Hendricks / Geoffrey Arend
The marriage of Mad Men star Christina Hendricks and character actor Geoffrey Arend should stand as an inspiration for geeks everywhere that hope to get the girl. Arend has had a measure of acting success and was hysterical in Super Troopers, but he clearly jumped up several levels in landing himself a red-headed bombshell like Hendricks. The pair, who were married in 2009, met in 2006 through Hendricks’ Mad Men co-star Vincent Kartheiser. They remain married to this day, thanks in part to a two-week rule which dictates they see each other every 14 days, regardless of work schedule.
3) Tom Green / Drew Barrymore
Fourteen years after the marriage of shock comic Tom Green and America’s sweetheart Drew Barrymore, one can’t help but wonder if the whole thing was just an elaborate gag. There was the 163-day duration of their nuptials, as well as the countless stunts they both engineered in advance of their wedding, including a hoax ceremony on Saturday Night Live that resulted in Barrymore “getting cold feet.” Impressively, the marriage to Green wasn’t even Barrymore’s shortest, as she and bartender Jeremy Thomas were divorced after just six weeks of marriage.
2) Dennis Rodman / Carmen Electra
Dennis Rodman has experienced his fair share of odd relationships – just ask Kim Jong-un. But perhaps none were more tumultuous than his marriage to Scary Movie star Carmen Electra. Getting married in November 1998 following just a three-month courtship, the NBA star filed for annulment from Electra after just nine days, claiming he was of “unsound mind” (when wasn’t he?). They later reconciled, but the ill-advised pairing only went on to last through to April 1999, a period that Electra would later refer to as the worst time of her life.
1) Billy Bob Thornton / Angelina Jolie
Actors Billy Bob Thornton and Angelina Jolie seemed to be a pair of kindred spirits during their brief, bizarre, whirlwind romance. Their dark, gothic sensibilities involved wearing vials of each other’s blood on their neck and featured a Vegas wedding which saw them get hitched in jeans and a gray tank top (her) and a printed shirt and trucker hat (him). Clearly, their 2000-2003 marriage represented a very different time in their lives, particularly in the case of Jolie, who has since become an A-list humanitarian and half of Hollywood’s most star-studded power couple alongside Brad Pitt.