8 Celebrity Cheaters Who Seriously Downgraded (And 7 Who Upgraded)

People that trade in their significant others for somebody else are sometimes happier for it but others have severe regrets about their choices.

Divorce rates in the United States stand at approximately 53%. It’s even higher in countries like Spain, Portugal, and Hungary which all have divorce rates that exceed 60%. It is estimated that Belgium has the highest divorce rate at 70% while Chile holds the lowest rate at 3%. The bottom line is that more long-term relationships fail than succeed.

People get married for different reasons. True love, unexpected pregnancies, and five-day liquor-fuelled benders in Las Vegas are just a few of the reasons. There are even some countries out there in which arranged marriages are still common. It’s the same with divorce. People end their relationships for a number of reasons such as incompatibility, financial stresses, and boredom. Of course, one of the main reasons that marriages break down is infidelity. It’s almost a sure thing that you or somebody that you know has engaged in a little side action. Some people get away with it but most cheaters eventually get caught and when they do there are plenty of hurt feelings.

People that trade in their significant others for somebody else are sometimes happier for it but others have severe regrets about their choices. Let’s take a look at 8 celeb cheaters who seriously downgraded and 7 who upgraded.

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15 Downgraded: Jesse James

Not to be confused with the famous American outlaw, Jesse James is a car and motorcycle customizer and was the host of Jesse James is a Dead Man and Monster Garage. James was married to his first wife between 1991 and 2002 but he kicked her to the curb to marry Janine Lindemulder who is an “adult entertainer”. He then traded Lindemulder in for actress Sandra Bullock who he married in 2005. The two seemed quite happy together but James obviously wasn’t content with his beautiful wife. After rumors of infidelity began to run rampant, James issued a public apology and accepted responsibility for his cheating ways. Bullock quickly filed for divorce. James downgraded when he married Alexis DeJoria in 2013. It will be interesting to see how long that relationship lasts.

14 Upgraded: Kim Kardashian

Kim Kardashian has been in her fair share of high-profile relationships and she seemed to always be upgrading. She was once married to Damon Thomas but it wasn’t long before she upgraded to Ray J, then again upgraded to Nick Cannon. She married Kris Humphries in 2011 but that marriage was nothing more than a short-lived sideshow. While still legally married to Humphries, Kardashian started a relationship with Kanye West which is one heck of a significant upgrade. The two were wed in 2014 and they have been in the media spotlight ever since. It seems that everything that Kim Kardashian does is calculated and upgrading to Kanye West has benefitted both. It’s nearly impossible to go through a day without hearing their names or seeing them on television or in magazines.

13 Downgraded: Eric Benet

Some guys just can’t stay satisfied and Eric Benet is one such example. The R&B singer came to prominence in the late 1990s with hits like “Act Like You Want It”, “Georgy Porgy”, and the smash hit “Spend My Life with You”. It got even better for him in 2001 when he married actress Halle Berry. Now, Halle Berry is a spectacularly sexy woman but it seems that she wasn’t quite good enough for him. Of course, Halle might have seen the signs of things to come when Eric was treated for sex addiction at some point during their marriage. Eric strayed and the beautiful Berry washed her hands of him. Benet went on to marry Manuela Testolini who is Prince’s ex-wife. Sure, Manuela is pretty good looking but she is a definite downgrade from Halle Berry.

12 Upgraded: Kevin Federline

Kevin Federline was a relatively unknown singer and dancer. He had performed as a backup dancer for some pretty big names including Michael Jackson, Justin Timberlake, and Destiny’s Child. He was engaged to Shar Jackson who he had been dating since 2001. In 2004, just before Shar gave birth to their son, Kevin flew the coop and fell into the arms of Britney Spears. Talk about a serious upgrade! The two got married after a whirlwind romance and K-Fed was suddenly thrust into the spotlight. His career blossomed and he appeared to be set to ride Britney coattails but the marriage lasted less than two years. Britney filed for divorce and Federline pretty much vanished into obscurity. He still shows up in the occasional guest role and on lists such as this.

11 Downgraded: Hugh Grant

Hugh Grant might come across as a smarmy stuffed shirt that a lot of guys would love to punch in the face but he has had a very successful movie career. He also managed to luck out in 1987 when he met and married the gorgeous Elizabeth Hurley. He made several movies throughout the late 80s and into the 90s including The Remains of the Day and Four Weddings and a Funeral. Just prior to the release of his 1995 film Nine Months, Hugh was caught with his pants down with a prostitute in Hollywood. The media attention was immense and his image took a beating. He still managed to make movies but his marriage disintegrated as a result of the embarrassing incident. He has since remained single and while he has probably had his share of great looking ladies since none could possibly be as hot as his ex-wife.

10 Upgraded: Brad Pitt

Jennifer Aniston is a very sexy woman and most guys would never dream of cheating on her. However, Brad Pitt isn’t your average dude. He’s been in loads of great movies and has won his share of awards. Seven, 12 Monkeys and the cult classic Fight Club are just a few movies in which he’s appeared. Pitt married Aniston in 2000 and remained married until Pitt had a fling with Angelina Jolie. Well, it was a little more than just a fling as Pitt dumped Aniston and eventually married Jolie bringing the term “Brangelina” into our vocabularies. Yes, Aniston is famous and she is definitely hot but Angelina has the larger star power and she’s hot too. There must have been trouble in paradise as the two parted ways recently.

9 Downgraded: Scott Disick

Scott Disick gained celebrity status as Kourtney Kardashian’s on-again-off-again boyfriend. Their relationship has been one of the subplots, if you could call it that, on Keeping Up With The Kardashians. Back in 2011, Scott bought an engagement ring for Kourtney but, as chronicled on Kourtney and Kim Take New York, Kourtney wasn’t too receptive of the idea. It’s really not too hard to understand why as the 33-year-old Scott had been caught cheating on a few occasions. Most recently, he was caught in a Costa Rican hotel room with some random chick during a Kardashian family vacation and the relationship has since ended. Disick is currently dating the 19-year-old Sofia Richie.

8 Upgraded: Ashton Kutcher

Ashton Kutcher started out as a Calvin Klein model before being cast as Michael Kelso in That ‘70s Show which ran from 1998 until 2006. He has also appeared in several movies and is noted for replacing Charlie Sheen on the television series Two and a Half Men. Kutcher and Demi Moore turned a lot of heads when they got married in 2005 – the veteran actress is 15 years his senior. They seemed to be making it work but Kutcher apparently went to a wild party and got it on with two women in a hot tub. He did this on his 6th wedding anniversary no less. As rumors of the infidelity were spreading, Ashton and Demi called it quits. Kutcher then upgraded to the smoking-hot Mila Kunis who was one of his co-stars on That ‘70s Show.

7 Downgraded: Tiger Woods

Tiger Woods doesn’t need much of an introduction. Up until a few years ago, Tiger was the biggest name in golf and looked to be a lock to break the record for winning the most majors. He seemed to have it all. He had oodles of cash, a clean image, and a beautiful wife named Elin Nordegren who just happened to be a model. She was exactly what you imagine when you think of the most beautiful member of the Swedish bikini team. Tiger’s entire world fell apart after his rampant infidelities were discovered by both Elin and the rest of the world in 2009. His golf game has gone south and he has been caught up in one scandal after another in the years since. Just when you think he’s hit rock bottom he manages to sink deeper.

6 Upgraded: Anna Nicole Smith

Although the term “gold digger” has been around for a long time, nobody has fit the description quite as well as Anna Nicole Smith. The blonde bombshell was an aspiring model and actress when she married Billy Wayne Smith in 1985. Her career never got off the ground and she was working as a stripper in the early 1990s. She was doing her act one night in 1991 when she met J. Howard Marshall, a filthy-rich oil tycoon. She dumped Billy and married the 89-year-old Marshall in 1994. Her wedding made headlines and her career suddenly took off. Her marriage to Marshall was brief as he passed away in August of 1995. Smith became tabloid fodder for the next several years before she died of a drug overdose at the age of 39 in 2007.

5 Downgraded: Ethan Hawke

Ethan Hawke had been in a few forgettable movies by the time he got his breakthrough role in 1989’s Dead Poets Society. His star quickly rose as he appeared in loads of films throughout the 1990s. One such film he did was called Gattaca and it was on the set of that movie that he started to date the lovely Uma Thurman. The two married in 1998 but it seems that Ethan had a thing for the hired help. Apparently, Ethan had an affair with the nanny that he and Uma had hired to tend to their kids. Uma caught wind of this and filed for divorce in 2004. Ethan stayed with the nanny, Ryan, and ended up marrying her in 2008. Granted, Ryan’s a pretty decent looking lady but she doesn’t hold a candle to Uma.

4 Upgraded: Dean McDermott

Dean McDermott is a Canadian actor who has been in a few movies and television shows but has mainly held bit parts. He was married to an actress named May Jo Eustache and the couple had one child. Meanwhile, Tori Spelling had carved out a pretty decent acting career and was married to Charlie Shanian. Tori and Dean met on the set of Mind Over Murder in 2005 and the two hit it off. In fact, they hit it off so well that they quickly divorced their respective spouses. The two married in 2006 and quickly began to chronicle their happy lives in a series of reality television shows. Dean has been riding Tori’s coattails ever since but recent rumors have surfaced that indicate their romance might be over after Dean was caught getting it on with another woman.

3 Downgraded: Eliot Spitzer

Eliot Spitzer was the governor of New York between January 1st, 2007 and March 17th, 2008. The career politician and former Attorney General of New York was involved in a few controversies such as “Troopergate” and his support for allowing illegal immigrants to obtain driver’s licenses but those were overshadowed when it was discovered that he had been paying thousands of dollars for the services of high-end prostitutes. Investigators claimed that he had spent around $80,000 on hookers over a period of several years. His approval ratings were low enough before these revelations came to light and they bottomed out afterward. His 26-year marriage fell apart and his career stalled. Spitzer’s attempts to revive his life in politics have failed and he has become an investor. He reportedly had a brief romance with a former spokesperson of his but he appears to be single.

2 Upgraded: Camilla Parker Bowles

Camilla Shand was born into privilege. She grew up in a moneyed family and married her first husband, Andrew Parker Bowles, in 1973. The couple had two children. We likely all remember that Prince Charles married Diana Spencer in 1981? We also know that the marriage became to come apart at the seams in the early 1990s as Charles’s infidelity was becoming a well-known issue. For several years before as well as during Charles’s and Camilla respective marriages, the two engaged in an ongoing affair. In 1995, Camilla got a divorce as did Charles and Diana a year later. It’s not like Camilla wasn’t already filthy rich and living the good life but now she’s in line to become Princess Consort when Queen Elizabeth dies and Charles accedes the thrown. I’m sure most of you would agree that it’s quite the upgrade for Camilla?

1 Downgraded: John Lennon

John Lennon met his first wife, Cynthia, in 1957 when they were both in high school. The stunning Cynthia heard about John’s obsession with Brigitte Bardot and she dyed her hair blonde. The two eventually married in 1962 just as Beatlemania was sweeping through the music world. John met Yoko Ono in either 1965 or 1966 and the two began to carry on an intimate relationship. Cynthia walked in on John and Yoko at one point and that was it for their marriage. John ended up marrying Ono in 1969 and the rest is history. The Beatles broke up and Lennon went on to enjoy a successful solo career although he was nowhere near as popular as the Beatles were. They say that love is blind and it must have been for Lennon to make such a shocking downgrade.

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8 Celebrity Cheaters Who Seriously Downgraded (And 7 Who Upgraded)