Hollywood Cheaters: The 10 Sleaziest Cheating Scandals in Hollywood

When I think about Hollywood and sex, I am reminded of an old song by a man named Cole Porter called Anything Goesfrom Cole’s musical of the same name. While it may take a few tries to catch all of the lyrics, I think one line really sums it all up. “In olden days a glimpse of stocking was looked on as something shocking, now God knows, anything goes.” Pop stars routinely hit the stage in costumes that would get them arrested in the street on Halloween. Taking it all off for Playboy is considered a wise career move and sex tapes or naked cell phone pictures barely raise an eyebrow. In all of this delicious depravity, is it really all that surprising that many folks in Hollywood get themselves wrapped up in cheating scandals? Let’s take a look back at some of the sleaziest cheating scandals Hollywood has ever seen. Some you may remember, some you may have forgotten and some you may not have heard about. Let’s get started.

source: people.com

10: Brad Pitt and Angelina Jolie

Were Angelina and Brad together before Brad and Jennifer split up? The rumors say yes but the couple says no. Which is true? Well, I suppose no one really knows aside from Brad and Angelina. While I would never condone cheating, I think Angelina and Brad handled their still budding relationship well, at least initially. They backed out of the spotlight, distanced themselves at press events and kept things as classy as possible considering the situation. There are far worse ways to handle such things.

source: dailymail.co.uk

09: Balthazar Getty and Sienna Miller

I really like Sienna Miller but the girl doesn’t make it easy. She seems to perpetually find herself playing the role of the other woman and not on the big screen. She originated the performance with Jude Law and then reprised the role for her affair with the very married Balthazer. She recently reunited with and separated from Jude. I want Sienna to find happiness because I do genuinely love this girl. Perhaps the first step in the process is to start looking at men that aren’t already attached.

source: mugabebraintelevision.blogspot.com

08: Jude Law and Daisy Wright

Jude once again proves, he’s the picture perfect boyfriend/husband by admitting to a month long affair with his nanny, Daisy Wright. Of course he didn’t fess up because it was the right thing to do or because a guilty conscience compelled him to. No, he came clean because Daisy took the story to the tabloids. I do give him a little bit of credit though. He could’ve lied but chose instead to tell the truth. I still love Jude, even if he is a bit of a pig.

source: people.com

07: LeAnn Rimes and Eddie Cibrian

Remember when LeAnn was sweet and innocent? What happened? A moment ago I said Brad and Angelina handled their possibly infidelity with class and mentioned things could’ve been worse. LeAnn and Eddie are a great example of that. The whole LeAnn and Eddie mess serves as a perfect example of how not to cheat on your spouse if you want people to continue liking you. After first denying an affair and embarking on separate photo ops with their respective spouses, LeAnn and Eddie left their partners and began flaunting their new relationship everywhere they could.

credit: Kevin Corkum/WENN

06: Billy Crudup and Claire Daines

These days, a guy leaving his wife for another woman isn’t really all that shocking. It happens all the time. This story was a bit different because when Billy left his girlfriend of seven years, the lovely Mary-Louise Parker, for Daines, Mary-Louise was seven months pregnant with his child. Low. Karma caught up with Billy a short time later, however, when Claire cheated on him with co-star Hugh Dancy. I love Claire, but that is some seriously shady stuff.

source: fanpop.com

05: Jesse James and Bombshell McGee

Jesse James is a douchebag. I don’t necessarily call him a douchebag because he cheated or even because he cheated on Sandra Bullock. I call him a douchebag because he single handedly made Bombshell McGee a quasi-celebrity and that is just unforgivable. Without Jesse, the world may never have been subjected to the moronic exploits of this brain dead bimbo with all the feminine charm of a chainsaw and I have a hard time believing the world wouldn’t be a better place for it.

credit: Gretchen Dow Mashkuri/WireImage.com

04: Tiger Woods and Everyone

I suppose if you’re going to cheat on your gorgeous wife and the mother of your children, you might as well go all the way with it. When the first affair broke, it opened the flood gates and soon there was an official mistress count. I can’t remember how many mistresses there were, eight or nine, I think, and it’s impossible to think of just one that was worse than the others, but Tiger set the standard for cheating scandals and paid dearly for it. His career is in the toilet and his reputation is right there with it. If anyone ever proved how incredibly stupid cheating is, it was Tiger.

source: dailymail.co.uk

03: Hugh Grant and Divine Brown

This little affair pretty much made Mr. Grant the poster boy for Hollywood cheaters. While dating Elizabeth Hurley, undoubtedly one of the most beautiful women in the business, Grant sought out the company of a hooker named Divine Brown for a little oral action. It didn’t go terribly well as both Grant and Brown were arrested and booked. Hugh later took the high road, went on The Tonight Show with Jay Lenoand not only admitted his transgressions but apologized as well. Cheating is wrong, but at least he was a man about it, saving some face and maybe even his reputation.

source: CBSnews.com

02: Bill Clinton and Monica Lewinsky

I tried hard to leave politicians off this list because I honestly don’t consider politicians celebrities, but I can’t make a list of famous cheating scandals without Bubba. The political sex scandal to end all sex scandals, the President of the United States was caught with his pants down getting a little oral action from an intern in the oval office. Bill Clinton did a lot of good things for the United States but he was no match for an ambitious intern named Monica Lewinsky and her blue Gap dress. When Bill cheated on Hilary, he not only brought shame to the office of President but also besmirched the fine name of cigars nearly beyond repair.

credit: Janet Mayer/PR Photos

01: Woody Allen and Soon-Yi Previn

In what was undoubtedly one of the creepiest and most shocking affairs of all time, Woody Allen cheated on long time girlfriend, Mia Farrow with Farrow’s 22 year old adopted daughter Soon-Yi Previn. Yes, technically Woody cheated on his girlfriend with his step-daughter. Woody later married Soon-Yi and they remain together to this day. Um, good for them?

Of course, the cheaters on this list are just ten of the worst. Dishonorable mentions go to:

  • Ali McGraw cheated on husband, Robert Evans, with co-star, Steve McQueen, whom she later married. McQueen later left McGraw for model, Barbara Minty. He died a year after he married Minty.
  • Billy Bob Thorton cheated on girlfriend, Laura Dern with Angelina Jolie whom he later married.
  • Blake Shelton cheated on his wife with Miranda Lambert whom he later married.
  • Kevin Federline cheated on girlfriend, Shar Jackson with Britney Spears whom he later married.
  • Bruce Springsteen cheated on wife, Julianne Phillips with Patti Scialfa whom he later married.
  • Clark Gable cheated on wife, Maria Franklin Printiss Lucas Langham with Loretta Young who later had his child, actress Judy Lewis.
  • Dave Navarro cheated on his wife, Carmen Electra with porn star, Jenna Jamison, proving if you’re going to be stupid enough to cheat on a woman like Carmen, you might as well do it with a pro.
  • David Boreanaz cheated on his wife with Rachel Uchitel who later became known as Tiger Woods’ mistress number one.
  • David Duchovny cheated on wife, Tea Leoni.
  • David Letterman cheated on his wife with staff member, Stephanie Birkitt.
  • Elizabeth Taylor cheated on husband, Michael Wilding, with Michael Todd whom she later married. Taylor later cheated on fourth husband Eddie Fisher with Richard Burton, who became husband number five.
  • Eric Benet cheated on Halle Berry. Yes, Halle freaking Berry.
  • Ethan Hawke cheated on wife, Uma Thurman, with nanny, Ryan Shawhughes whom he later married.
  • Frank Gifford cheated on wife, Kathy Lee Gifford, with flight attendant, Suzen Johnson.
  • Humphrey Bogart was long rumored to have cheated on his wife with 19 year old Lauren Bacall.
  • Ingrid Bergman was married to Aron Petter Lindstrom when she began her affair with Roberto Rossellini who was married to Marcella De Marchis.
  • Jack Nicholson cheated on many woman, most notably wife Anjelica Houston with Rebecca Broussard. The affair came to light when Broussard revealed she was pregnant with Nicholson’s child.
  • Kobe Bryant admitted to cheating on his wife, Vanessa, with hotel employee, Katelyn Faber, after Faber accused him of sexual assault.
  • Marilyn Manson is rumored to have cheated on wife, Dita Von Teese with 19 year old (at the time), Evan Rachel Wood.
  • Peter Cook cheated on wife, Christie Brinkley with 18 year old Diana Bianchi.
  • Prince Charles cheated on Princess Diana with Camilla Parker-Bowles. Princess Diana later confessed to an affair with James Hewitt, her riding instructor.
  • Robert Rodriguez cheated on his wife with his leading lady, Rose McGowan.
  • Tiki Barber cheated on his wife with an intern.
Who do you think is the worst of the worst? Sound off in the comments section below!