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8 Two-Timing Actors That Did Worse (And 7 Who Did Better)

Hollywood has tried some scandalous affairs in the court of public opinion, here are 8 classics that make us cringe, and 7 that make us smile

For better or worse, celebrities hold an important place in culture. All art, including movies and television, acts as some kind of mirror to aid people in their search to understand themselves and the world around them. With that unrealistic goal in mind, many people look to celebrities as heroes, to emulate and idolize. Built into this search is an inquiry into the love lives and personal foibles of each celebrity.

Audiences love to see their heroes succeed in movies they love, but they also don’t mind seeing them fall a little bit, and some harsh reality in Hollywood aids the credibility of the movies it produces. Real heroes are human; rather than punishing these celebrities for that, true fans should be thanking them for being honest and authentic.

In an effort to take the good with the bad, with the noblest intentions of exploring celebrity and humanity at the same time, this article explores cheating actors. Specifically, this list will explore not only the cheating act itself, but also the weight and mechanics that scandal holds in celebrity culture, then and now.

With that in mind, desperately trying to learn something, here are 8 Actor Cheaters Who Seriously Downgraded, And 7 Who Upgraded.

15 Hugh Grant - Downgraded

Starting off our list is one of the all time worst downgrades, Hugh Grant cheating on Elizabeth Hurley. This one has stood the test of time: in 1995, Grant was arrested for ‘mature acts in a public place” in Los Angeles after engaging with an, admittedly beautiful, lady of the night named Divine Brown. At the time, it seemed an unforgivable, shocking act, but what Grant described as a moment of insanity, Hurley forgave and the couple stayed together for five more years.

Grant’s handling of the matter bears some study. In 1999, this was a national Hollywood scandal that Grant began to climb back from. By getting ahead of the story and admitting fault immediately, Hugh Grant got himself off the hook and back into the spotlight. He and Hurley split in 2000, but after being a romantic comedy megastar for another decade, his career was salvaged.

14 Meg Ryan - Upgraded

Proof of Life (2000) is the story of a kidnapped man (Wiliam H. Macy) whose wife (Meg Ryan) has an affair with the hostage negotiator (Russell Crowe) hired to bring him back. Thankfully Meg Ryan and WIlliam H. Macy aren’t married in real life, but another relationship in that triangle did come into reality.

Meg Ryan was married to Dennis Quaid at the time, but on Proof of Life, her affair with Crowe brought that marriage to an end.

This upgrade follows in the long tradition of affairs inspired by on screen roles. Something about playing the parts of two adults entering a forbidden romantic relationship causes the sparks to fly and then it turns into an office romance. Fortunately for audiences, the movie was improved by the hidden feelings behind Crowe’s gruff special agent comforting Ryan’s grieving spouse.

13 Kristen Stewart - Downgraded

Real life chemistry supported the Twilight franchise for a long time until leading lady Kristen Stewart cheated on leading man Robert Pattinson in 2012. Their relationship added depth and real emotion for fans of the books and movies. Stewart and director Rupert Sanders were working on Snow White and the Huntsman when they had their passing fling. The relationship barely got off the ground, but it caused Sanders some serious damage control with his wife and kids and put a big dent in Stewart and Pattinson’s working relationship.

After public outing, outcry, and persecution, Kristen Stewart released a public apology for the affair, claiming she never meant to hurt Pattinson, but she said she still wasn’t able to avoid the negative press from women and fans. As politely as possible, we’ll call it a downgrade.

12 Angelina Jolie - Upgraded

Regardless of the real life ramifications of celebrity affairs, in some cases, for the purposes of this list, the quality of the film come first. That’s why Angelina Jolie’s affair with Brad Pitt is a definite upgrade for almost all parties. Their chemistry on screen was captured incredibly in Mr. and Mrs. Smith (2005). Officially, that movie is about two spies who find out they’ve been hired to kill each other. It’s a solid action movie, somewhere in between a poor man’s The Matrix and a poor man’s The Transporter, but under that, there’s a far more interesting record of the day to day development of the relationship between two mega stars.

Hollywood and American celebrity at large got an upgrade with this affair, since it kicked off one of the most iconic power couples in the world in Brad and Angelina.

Even though Brad cheated on Jennifer Aniston, fans got over it pretty quickly when they saw two celebrities being drawn to each other like forces of nature.  

11 David Letterman - Downgraded

With a new experiment on Netflix this month, David Letterman returns, at least to monthly, relevance. Here’s one reason he’s earned that beard: in 2009, he admitted, on his show, that he had an affair with an employee. The relationship with his assistant, Stephanie Birkitt, came to the public eye when Letterman began being blackmailed about it by another producer within CBS.

Even though this was a downgrade, the lesson here is in how Letterman went public about it. He happened to have an extremely popular Late Night show, so he spoke to his audience and told the truth. All accounts of Letterman in the days leading up to and after the scandal say that he was absolutely devastated by the events, horrified about losing his family. This event definitely tarnished his reputation and trust, but he's managing to save his career.

10 Jennifer Lopez - Upgraded

Up next on our list, we have Jennifer Lopez cheating on Cris Judd with Ben Affleck in 2002. This was the relationship inspired by the infamous flop Gigli.

Even though that movie didn’t do will with critics or audiences and JLo’s acting career never quite crystallized, this is still an upgrade for Jennifer Lopez for taking the next step in her romantic star power.

Bennifer was also an inescapable touchstone of the early 2000s, si kudos to Jen and Ben both for allowing the tabloid media to explore this relationship in the early days of the internet and developing the pre hashtag trending topic. Any romantic entanglement that people can look back on 15 years later and still remember fondly deserves an honorable spot on this list.

9 Sienna Miller - Downgraded

Even another 15 years won’t reverse the decision on Sienna Miller’s flirtatious extracurricular activities. This downgrade is for Miller cheating on Jude Law in 2005 with James Bond, Daniel Craig. Law would later go on to get caught cheating with his nanny and their marriage would eventually dissolve anyway, but Sienna’s indiscretion opened up an even messier situation, involving another celebrity and a sensitive voicemail message.

A hacked message made headlines when this affair surfaced that recorded Miller telling Craig “I love you.” After the tabloid discourse, Sienna Miller was judged to be using the phrase a bit too casually for such a brief encounter, despite her protests that it was a friendly usage. This downgrade is a low point on this list of trysts for the the startling way it unfolded in the public eye.  

8 Evan Rachel Wood - Upgraded

In 2006, Marilyn Manson cheated on his wife Dita Von Teese with Evan Rachel Wood. Even though there was an eighteen year age difference between Manson and Wood and his and Von Teese’s marriage ended just a few years later, this was still an upgrade for Wood, in appreciation for her abilities to push the boundaries in exactly the right ways.

Evan Rachel Wood, who was 18 years old when she met Marilyn Manson, doesn’t regret any of their on again off again relationship and teaches us all about body positivity.

Despite the relative youth of one half of this relationship and the relative insanity of the other half, this affair and its ensuing controversy was dealt with maturely in this media age, and serves as a textbook example of how to conduct a radical relationship in the press. 

7 Jude Law - Downgraded

The wake from this relationship keeps waving, Jude Law takes the seventh spot on this list, and a big downgrade, for his affair with his nanny while married to Sienna Miller. Usually, in relationship scenarios, it’s preferable to have a guilty party and innocent party, so that there are concrete lessons to be learned. This relationship was apparently just doomed from the start and everyone’s better off out of it.  

The downgrade is specifically for the handling of this affair through the UK and US tabloids. Law and Miller, from one perspective, may be early victims one and two of the hyper litigious, hacking tabloids of the mid 2000s. From another perspective they’re just two people, in a bad relationship, who happened to collide and bounce off of each other in front of every camera and paparazzo.

6 Billy Bob Thornton - Upgraded

The time in 1999 when Billy Bob Thornton cheated on Laura Dern with Angelina Jolie belongs in the upgrade category. His ability to phase from one woman to the next is almost superhero like, it’s surprising he’s not in an X-Men movie, if not an American James Bond spoof. Thornton represents the lightning rod in celebrity culture for bad press and lascivious scorn. No public apologies or explanations are ever made for the relationships Thornton breezes through, if a relationship will have any meaning for this character, it must be brief and intense.

This upgrade is awarded for the formalization of the Hollywood heel.

His relationship with Jolie introduced one of the most public tabloid romances, if not always the most mature. They met on the set of Pushing Tin (1999) and were together for four years. Meanwhile, they were Hollywood’s baddest couple and they directly contributed to a generation needing to coin the phrase ‘overshare’.

5 Billy Crudup - Downgraded

In 2003, the current Henry Allen in Justice League and the DCU, Dr. Manhattan in Watchmen, and Russell Hammond in Almost Famous, Billy Crudup, cheated on long time girlfriend Mary-Louise Parker. Crudup and Claire Danes were starring together in Stage Beauty (2005), but that doesn’t make this downgrade any better.

Time has been especially unkind to this over publicized tryst once Weeds fans remember that Parker was seven months pregnant with their son at the time. Parker holds no ill will about the dissolution of the their eight year relationship, however. She even had the last word, penning a forgiving reflection about the encounter in her memoir of romantic letters, Dear Mr. You. In it, Parker reminds us all that life is a journey and even the downgrades should be appreciated for their role in the growing process.

4 Elizabeth Taylor - Upgraded

Elizabeth Taylor appreciated the journey of life as she upgraded her way through Hollywood, this time with her affair with Eddie Fisher, then the husband of Debbie Reynolds. Taylor was the archetype for so much of how feminism is handled in Hollywood today, along with Audrey Hepburn, Marilyn Monroe, and Grace Kelly.

When this scandal rocked Hollywood, it was one of the most intimate, well documented, high profile events of the time.

Debbie Reynolds, maybe best known for Singing in the Rain, had been best friends with Elizabeth Taylor, the eponymous Cleopatra and the pair, along with their husbands, had been at the front of the paparazzi boom of the time. When Taylor’s husband died in a horrific plane crash, events unfolded like a Greek tragedy in front of America’s eyes. To comfort her in her grief, Elizabeth Taylor found solace in the arms of her best friend’s husband, Eddie Fisher. Love conquers all, and thankfully Reynolds and Taylor patched their friendship over time.

3 Ethan Hawke - Downgraded

Adding to the cheating with his nanny Mt. Rushmore, Ethan Hawke earned his place on the monument in 2004, cheating on Uma Thurman in the middle of their seven year marriage. After meeting on the set of Gattaca, the two married in 1998, but monogamy wasn’t meant for Ethan Hawke as he’s since elaborated in many interviews.

This separation is amicable now, but the exact proceedings of the divorce took a full two years before they were finalized. These days, Hawke chalks the indiscretion up to an evolving brain and the folly of youth. Regardless of how he tries to dress it up, this is still a downgrade. Hopefully in private, things between Thurman and Hawke are smoothed over, but this was a publicity and romantic misstep, and Uma deserved a bit better. Hawke’s career hasn’t suffered, however, as Hollywood and movie fans everywhere are still endeared by his boyish (even at this age) curiosity for the world. 

2 Ingrid Bergman - Upgraded

Ingrid Bergman’s breakthrough into film stardom opened a lot of doors for how an actress can take control over her career. Bergma's difference was an inseparable part of her character.

Her refusal to apologize for any variation from the norm continued in her affair with Italian film director Roberto Rosselini in the late 1940s.

Even after Casablanca in 1942, Bergman was blacklisted by the isolationist, anti-communist, anti-immigrant policies of Hollywood during the Red Scare. This drove her overseas to pursue a career with the radical Italian director. Due to Bergman’s determined nature, and her husband’s reluctance to finalize the divorce, her reputation and career suffered in a hypercritical paparazzi. Today, Ingrid Bergman stands out as a woman who didn’t let Hollywood’s oppression dictate her behavior and as a tragedy of how those attitudes can affect an actor’s career and film at large.

1 Jack Nicholson - Downgraded

For an example of how a male actor’s indiscretions can’t affect their career, students of Hollywood need look no further than Jack Nicholson, notorious equally for his infidelities and great movies. His seventeen year relationship, across the 70s and 80s, with Anjelica Huston was riddled with affairs and emotional manipulation, as detailed in her memoir, Watch Me.

The most stunning, steep, part of this downgrade is the amount of candid talk and honest discussion there’s been about Nicholson’s erratic, substance fueled, behavior over the years, yet the actor continues to carry on his career and reputation. Admittedly he’s retired over recent decades and his reputation hasn’t remained wholly intact, but he’s still a good example of an actor who's made their career more about their caricature and on-screen performance than their actions and real life impact on people.

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8 Two-Timing Actors That Did Worse (And 7 Who Did Better)