There are a lot of elements that go into making sure you are in a healthy relationship. Sure, physical attraction is important, but it’s really only the tip of the iceberg in terms of making things work. For the 20 gentlemen below, this is great news as they are definitely on the lower end of the attraction scale in comparison to their female counterparts. It’s hard to blame some of them, especially considering we have two women below who ranked #1 on Maxim’s Top 100. Other relationships may not seem to be a huge shift in attraction levels, but you may be blown away by some of the biggest age gaps in Hollywood marriages. Some of these couples are still together today, whereas others were quick flings that both parties probably regret (such as Madonna and Dennis Rodman).
Other relationships below, well….we ain’t sayin they’re gold diggers, but some of these women certainly aren’t messing around with poor individuals. Mary-Kate Olsen may have fallen out of the spotlight, but do you know how much her new partner (who honestly, could be her dad) is worth? And who could forget Anna Nicole Smith?
Below we’ll not only outline who these people are but also how their relationships came together. Cameron Diaz was openly anti-marriage for most of her career, but do you know how long it took her to get married to her husband Benji Madden? You’ll also be shocked at how many of these relationships started as affairs! There is even one guy on here that slept with not one, but two of the main characters from Friends, and let’s just say he must have a fantastic personality.
With the list ranging from actors to musicians to even the next potential president of the United States, there is no shortage of less than conventionally attractive guys who have landed some of the sexiest women in the world. There is even one guy on this list that landed 3 of the sexiest women, all at once.
20. Marilyn Manson and Evan Rachel Wood
Who Are They? You know that the fanbase of Marilyn Manson must love everything about him, and that includes his iconic look, but could you imagine dating him? You’d get that white makeup everywhere!
To each their own, because Evan Rachel Wood said that when she first met Manson, it was his frequent use of black eye liner that really caught her attention. Evan Rachel Wood is an incredibly talented actress, who may be best known for her role in the 2003 drama Thirteen, as well as appearing in True Blood.
Are They Still Together? No, the two met in 2007 and started dating but they split up in 2008. They cited that they needed time apart so they could focus on their careers. It was reported in 2010 that the two had gotten back together and were even engaged in January, but the relationship fell apart by August of that year.
Wood then got back together with her former partner, Jamie Bell, but they separated after 19 months of marriage.
19. Griffin Guess and Marissa Miller
Who Are They? That unbelievable blonde is none other than Marissa Miller, who just happens to be one of the most successful models of all time. On top of her various modeling projects, Miller spent time as a Victoria’s Secret model, and in 2008 was number one on Maxim’s Top 100. Keep reading below and you’ll see that she isn’t the only #1 to make our list.
Throughout most of her modeling career, she’s dated Griffin Guess who she started seeing shortly after her separation from former husband, Jim Miller. Guess, to his own credit, is a successful music producer and talent manager.
Are They Still Together? Yes! The two got married in 2006 and have two children together. Their first son was born in December 2012 and their second son was born in May 2015. I guess Miller digs the facial hair and semi-rat tail.
18. Ric Ocasek and Paulina Porizkova
Who Are They? Ric Ocasek is an incredibly talented musician who is most prominently known for his time in the rock band the Cars. It was during the filming of the music video for the song “Drive”, that Ocasek met Paulina Porizkova in 1984.
Porizkova is a talented model and actress, and in 1984 she was on the cover of the Sports Illustrated’s Swimsuit Issue. She was only 18 years old at the time, and Ocasek was 34.
Are They Still Together? Yes! They have two children together; Jonathan who was born in 1994 and Oliver who was born in 1998. Ocasek was still married at the time when they met, but it did not stop their courtship and the two were married in 1989. It was the third marriage for Ocasek.
17. Sacha Baron Cohen and Isla Fisher
Who Are They? Now if we’re being completely honest, Sacha Baron Cohen definitely doesn’t clean up all that bad. But you also have to factor in that for part of the year, he may be sporting the Borat or Bruno look that made him famous. I know Fisher loves him, but that’d still be a lot to take! Fisher is also a talented actress, best known for her role in the comedies Wedding Crashers and Hot Rod.
Are They Still Together? Yes! The two met in 2002 at a party in Sydney, Australia and were engaged in 2004. They then got married in 2010.
Not only are they still together, but the efforts Fisher put into getting married to Cohen were pretty remarkable. Fisher did not want to get married until she converted to Judaism because it was important to Cohen. It took her three years of study, but she was converted in 2007.
When talking about the experience, Fisher said “I will definitely have a Jewish wedding just to be with Sacha. I would do anything—move into any religion—to be united in marriage with him. We have a future together, and religion comes second to love as far as we are concerned.”
16. Hugh Hefner and Holly Madison, Bridget Marquardt and Kendra Wilkinson
Who Are They? Hugh Hefner is the founder of Playboy Enterprises and with a net worth of over $43 million, you can imagine he’s had himself a pretty comfortable life. It also probably helped that for several years, Hefner had a relationship with Holly Madison, Bridget Marquardt and Kendra Wilkinson. The three women appeared on the reality show The Girls Next Door where they talked about their life dating Hefner and living at the mansion.
Are They Still Together? No, on all three fronts! Both Madison and Wilkinson ended their relationships with Hefner in 2008 and in 2009, Marquardt ended her relationship with Hefner. Since then, Hefner has gotten married to Crystal Harris in 2012. Harris was 86 and Harris was 26. Hefner was also dating the two Shannon Twins when he started dating Harris in 2009, but it appears that since their marriage, he has just been with her.
15. Russell Brand and Katy Perry
Who Are They? Russell Brand is one of the funniest comedians in Hollywood. He not only has experience as a stand-up comedian, but with roles like Forgetting Sarah Marshall under his belt, it’s clear that he knows how to make you laugh on film as well. Perhaps that’s how he wooed the affections of music superstar Katy Perry. Perry’s next album is expected to come out later this year and the first single “Rise” was made the anthem for 2016 Summer Olympics.
Brand also has a very public past battle with both sex and various drug addictions. This made it all the more shocking when these two started dating. The real tragedy is that she wasn’t able to convince him to button up his shirts.
Are They Still Together? No, the couple met in 2009 after Perry filmed a cameo for the movie Get Him To The Greek. Funnily enough, her role ended up getting cut from the movie. They started dating in September and were engaged by New Year’s Eve.
They then proceeded to get married in October 2010 but filed for divorce a little over a year later. In the Katy Perry documentary, it was revealed that Perry’s unwillingness to have children and conflicting schedules as being fundamental reasons for their split.
Brand has been in a relationship with Laura Gallacher since 2015, and it was announced earlier this year that the two are expecting their first child. It was reported that after their divorce that Perry was distraught and even complimented suicide.
14. Benji Madden and Cameron Diaz
Who Are They? Cameron Diaz is definitely one of the most recognizable actresses in Hollywood. At least you better hope so, considering she started her career in 1992! Diaz is also going to reprise her role as Princess Fiona in Shrek 5 which is scheduled to release in 2019. The gentleman to her left is Benji Madden who is best known for being the guitarist in the band Good Charlotte. The band started in 1995 and Benji is currently also a coach on The Voice Australia.
Are They Still Together? Cameron has dated several prominent people, including Alex Rodriguez, Justin Timberlake, and Jared Leto, but it was Benji Madden that was able to outlast them all. The two got married on January 5th, 2015 after only a 17-day engagement. They had met 7 months earlier after being introduced by Nicole Richie, who is married to Joel Madden. The marriage came as an even bigger shock considering Diaz had come out in the past on several occasions denouncing the institution of marriage and saying it wasn’t for her. As you can briefly see in the above photo, Madden has tattoos all over his body, including a large Benjamin Franklin on his back.
13. J. Howard Marshall and Anna Nicole Smith
Who Are They? Anna Nicole Smith was an incredibly popular model who posed for Playboy, FHM and Vanity Fair, among many others. One of her big downfalls came in 1994 when The New York magazine posted an unflattering picture of Nicole Smith on the cover squatting down and eating potato chips. It also had the title “White Trash Nation,” and Nicole Smith actually sued the magazine for $5 million.
It was in 1991 when she met J. Howard Marshall, who was an oil tycoon with an estimated fortune worth $1.6 billion. Smith was working at a strip club at the time, and Marshall won her over after buying several expensive gifts. Smith was married at the time, but in 1993, divorced her husband and in 1994 married Marshall. She was 26 years old at the time, and Marshall was 89.
Are They Still Together? No, they’re both actually dead. Marshall died 13 months after his marriage to Smith. Smith alleged that she never made love to Marshall, never lived with him and only kissed him roughly 10 times. Smith died in 2007 due to a combination of drug intoxication and the sleeping medication, chloral hydrate.
12. Francois-Henri Pinault and Salma Hayek
Who Are They? Salma Hayek is absolutely gorgeous and incredibly talented. She became most prominent in the early 90s with several great films, but it was in 2002 when her movie Frida really brought her to fame. While she did not win, Hayek was nominated for a Best Actress award for her performance.
The male on her arm is Francois-Henri Pinault, who is the CEO of Kering. While he may not be making his way to the big screen, it was announced in 2013 that Pinault and his family had a net worth of $15 billion.
Are They Still Together? Yes! While it is not clear when they started dating, Hayek announced her engagement (and pregnancy) on March 9th, 2007. Hayek gave birth to their daughter, Valentina in September and they were married on Valentine’s Day in 2009 in Paris. Later that year they had another ceremony in Venice, because when you’re worth billions, why not throw two weddings?
11. Adam Duritz and Courtney Cox
Who Are They? I guess when you’re in a band like Adam Duritz, you need to be able to prove you can rock out, but those dreds are really just not a good look. Duritz is best known for his time in the band Counting Crows and he is labeled as being the primary composer of the band. Courtney Cox is best known for her iconic role in Friends. While she has acted since, it’s always going to be hard for her to escape the shadow of Monica Gellar.
Are They Still Together? No, but Cox definitely has a thing for musicians! Cox had previously dated Ian Copeland who was a rock promoter and Michael Keaton. Duritz and Cox had a fling in 1995, which was also the same year that Duritz allegedly also won the affections of Jennifer Aniston.
Cox got married to David Arquette in 1999, but the two were divorced in 2013. Since then, Cox started dating (and is now engaged) to the musician (shocker) Johnny McDaid who is in the band Snow Patrol.
10. David Cross and Amber Tamblyn
Who Are They? If you don’t know who David Cross is, I’m just jealous of you because Arrested Development is one of the best TV series of all time and it means you still have the pleasure of experiencing it for the first time. Cross is hilarious in everything he appears in, including being the animated voice of Crane in the Kung Fu Panda franchise. Amber Tamblyn is a fellow actress who is best known for appearing in Joan of Arcadia and 127 Hours. While Cross is not hideous, that facial hair is definitely not doing him any favors.
Are They Still Together? Yes! The big shocker in their relationship may not be their appearances, but their age gap. At the time of their marriage in 2012, Cross was 48 years old and Tamblyn was only 29! The two were engaged in August 2011 after dating for two years. They then got married in October, 2012 but do not have any children together.
9. Simon Cowell and Carmen Electra
Who Are They? Now let’s be honest, Simon Cowell probably isn’t the most unattractive guy on this list. But he’s also probably the only one who could pull off just wearing a black shirt 90% of the time and still date a supermodel.
Carmen Electra is a former Playboy model and actress. Proving that she isn’t shy of dating unconventionally attractive guys, Electra was also briefly married to Dennis Rodman.
Are They Still Together? No, while many of these relationships ended in love or marriage, Cowell and Electra only dated briefly from December 2012 to February 2013. Cowell is definitely talented, but can you imagine sleeping with the guy? Talk about always being worried about getting criticized. The relationship ended after it was reported that Cowell was caught cheating on Electra.
8. Marc Anthony and Jennifer Lopez
Who Are They? If we’re being completely fair, if you’re standing next to Jennifer Lopez you’re probably always going to look pretty average by comparison. People in the past have attacked Anthony for looking far too skinny, in particular in his face.
Lopez is a famous musician, but with various appearances on television and movies, it’s clear that she is one of the most recognizable faces in Hollywood.
Are They Still Together? No! Lopez started dating Marc Anthony in January 2004, shortly after the end up her engagement with Ben Affleck. The two were married later that year and in 2007, Lopez announced that she was pregnant with twins. The two sold the rights to the first baby photos to People magazine for $6 million.
7. Colin Farrell and Britney Spears
Who Are They? Colin Farrell‘s acting stock may never be higher than it is right now. He’s one of the leads in Fantastic Beasts and Where To Find Them and was also outstanding in True Detective. Who is Britney Spears? Only one of the biggest musical artists of all time, so you can imagine dating her would be a pretty impressive them to also put on your resume!
Are They Still Together? No! In fact, at the time, Farrell tried to downplay the relationship. The two dated in 2003 after they met on the set of Farrell’s movie S.W.A.T. Spears went on to have a prominent (and short-lived) relationship with Kevin Federline, but neither star seems to currently be linked to anyone.
6. Mary-Kate Olsen and Oliver Sarkozy
Who Are They? Mary-Kate Olsen is best known for appearing on Full House with her twin sister, and honestly, that’s about the extent of her acting career that is worth talking about. But when you get famous as a kid, there will always be people who remember who you are. In later years Olsen appears to have had some plastic surgery, but that doesn’t make her relationship with Oliver Sarkozy any less weird. Sarkozy is a French banker and his half-brother is the former President of France.
Are They Still Together? Yes, the two got together in May 2012 and were then married in November 2015. If we’re being honest though, doesn’t Sarkozy look a lot more like her dad and less like her lover? With his net worth of close to $60 million, you can imagine at least Olsen is living pretty comfortably.
5. Shaun White and Bar Refaeli
Who Are They? Now to be fair, of any guy on this list, Shaun White may very well be the coolest. One of the most successful snowboarder and X-Games competitor, where he holds the record for the most gold medals. That doesn’t mean he’s necessarily good looking though! The above photo is definitely flattering for White, who is often seen with long, disheveled red hair, proving that it’s clear that White did not get to where he is because of his looks. On the other hand, his supermodel girlfriend Bar Refaeli is known as one of the sexiest women in the world. Like Marissa Miller, Bar Refaeli was also listed as #1 on Maxim’s Hot 100 list, but for the 2012 issue.
Are They Still Together? No, their romance was a brief one back in 2012. Perhaps White complimented her on her Hot 100 award! Their biggest fling came from a report in which White and Refaeli were all over each other over Memorial Day weekend.
4. Justin Long and Kate Mara
Who Are They? Justin Long definitely isn’t incredibly ugly, but it’s almost impossible to not picture him as the Mac guy or as his incredibly dorky role from the comedy Dodgeball. Long made his first break into Hollywood with a role in Galaxy Quest back in 1999 and in 2016, is appearing in the movie Ghost Team. Kate Mara is a talented actress who you may best know from her role in House of Cards or American Horror Story.
Are They Still Together? No, the two only dated briefly back in 2011. The relationship sadly came to an end for Justin Long when Kate Mara left him to get back with her ex Max Minghella. Want to make things even more awkward? They were all filming the same movie 10 Years together.
3. Donald Trump and Melania Trump
Who Are They? I’m not even going to entertain for a second that you don’t know who Donald Trump is. The former businessman turned presidential candidate is arguably one of the most powerful men in the world. That doesn’t mean there haven’t been years of jokes at his expense, in particular, toward his awful hairstyle. At least to his credit, he seems to be getting better looking with age.
The woman with him is Melania Trump and when she isn’t busy plagiarizing speeches, she can probably be seen supporting The Donald. Melania is a former model, and in 1992, won an international modeling contract which allowed her to model in Paris and Milan, before locating to New York in 1996.
Are They Still Together? You better hope so! Trump and Melanie met in 1998 but did not immediately start dating. They ended up getting engaged in 2004 and were married in 2005. The two have one child together, Barron William Trump, who Melania gave birth to in 2006.
2. Geoffrey Arend and Christina Hendricks
Who Are They? Christina Hendricks is arguably the most beautiful redhead in Hollywood and is best known for her role of Joan Holloway on the series Mad Men. You may be blown away to learn that she’s actually a natural blonde! Hendricks started dying her hair at the age of 10 because she loved the book Anne of Green Gables.
You may best know Arend from being the guy in Super Troopers who has to eat all of those Shrooms at the start of the movie. Arend most recently appeared in The Angry Birds Movie in which he voiced the Day Care Teacher.
Are They Still Together? Yes! Hendricks got married to Geoffrey Arend in 2009. When talking to Health magazine in 2014, Hendricks opened up about the fact they have agreed that they are not interested in having children. Absolutely nothing wrong with that decision, and hopefully they have nothing but full support for making a decision that works the best for their lives.
1. Dennis Rodman and Madonna
Who Are They? Madonna is one of the most successful musical artists of all time. As well as this, she’s been an iconic sex icon for decades and one look at her makes it easy to see why. The giant to her right is none other than Dennis Rodman who just happens to be one of the best NBA players of all time. He hadn’t quite gone off the handle yet, but Rodman was known for his extreme personality both on and off the court.
Are They Still Together? No, Dennis Rodman and Madonna only dated for a couple of months. At the time, Rodman was already one of the most dominant players in the league, making it at least understandable as to why they connected. The two allegedly had a fling in 1996, and in Rodman’s biography I Should Be Dead By Now, Rodman wrote a story about how he was playing poker in Las Vegas when he got a call from Madonna saying she was ovulating and to get his ass to New York. So naturally, Rodman flew to New York and did the deed. While they did not conceive a child in their few short months together, Rodman wrote “Turned out Madonna was a cool individual. She had her s*** together. And she wasn’t just in it for stud services. She wanted to get married – at least I think she did.”
It was also reported that the two had a two-month affair in 1994.