The Top 10 Worst Adulterers

Greg RiotAnalyst IDecember 14, 2009

Tiger Woods’ women are coming out of the woodwork to slam his reputation into a water hazard, but he isn’t the only infidel to grace the public’s scorecard.

In case you’ve lost track, there are least nine other jackasses that deserve public mention. Amongst them are these fine gentlemen. Thanks for lowering the bar, fellas!


10. David Letterman

David Letterman avoided public scrutiny by addressing his embarrassing internship affairs during a comedic monologue during an episode of Late Night With David Letterman. Of course, none of us were surprised that Letterman banged his interns.

Seriously, were you even remotely shocked? Letterman gave a whole new meaning to his production company, which is aptly named “Worldwide Pants Inc.”


9. Sen. Larry Craig

Sen. Larry Craig beat out Gov. Mark Sanford on this list, despite Sanford disappearing from office to skip to Argentina and use taxpayer money to fund his extramarital affair.

I know, it doesn’t seem like it could get better than that, right? Well it can if you replace “Argentina” with “public washroom.”

You know that scene in the TV series Dexter, where Angel is looking for some inappropriate hooker sex and ends up hitting on an undercover cop?

It’s actually a pretty funny scene when the fake hooker whips out her badge, and Angel has this absolutely devastated look on his fat face.

Well take that and pretend you’re trying to get a homosexual blow job in a public bathroom…from a police officer in the adjacent stall. Whoops.


8. Rick Pitino

I guess if you do something immoral, you just pray to God that it won’t come back and bite you in the ass, especially if you’ve been married for over 30 years.

Yet there was Pitino this summer, defending himself that he “raped” a woman in a restaurant behind closed doors in the kitchen of a local restaurant that had closed for its business day and only remained somewhat open to give Pitino a cheaper alternative to a motel.

The harlot in this case is Karen Cunagin Sypher, who’s married to Tim Sypher (also known as Pitino’s equipment manager at Louisville). It gets even greasier when Pitino paid Cunagin $3,000 to administer a “full court press” to her ovaries. Yikes.

Somehow, Pitino avoided being boxed out by Louisville despite this entangled mess. It must be the equivalent to an “and 1” for Pitino: He avoided an illegitimate child, retained his job, and somehow this got swept under the rug absurdly quickly.


7. Jude Law

Jude was caught cheating on girlfriend Sienna Miller and thankfully halted the onslaught of the “Jude Law Overload” of the early 2000’s. His alleged mistress was their nanny.

Law gets extra points for being a deadbeat dad after it was announced this summer that he had fathered the child of model Samantha Burke in 2008, which was proven during paternity tests despite Law vehemently denying the allegations.

With Law and another British actor on this list, are you ever going to trust an attractive, witty British chap just because they have a sexy accent?


6. Kobe Bryant

Kobe taught us all a serious lesson, and Tiger Woods should take notes.

The Lakers’ superstar was virtually convicted of raping a 19-year-old girl in Utah while being married to his high school sweetheart and practically bought his way out of it by settling with the girl, and slipping a $4 million ring on his wife’s hand as a token of his apology.

Then what did he do? He went on to become perhaps one of the top 5 NBA talents we have ever known. Had his career gone the way of Tyson’s in the post-ear-munching debacle, Bryant would be a sad laughingstock in basketball lore.

Instead, he’s considered one of the greatest basketball players of all time and we hardly even mention his affair, even though they were apparently non-consensual.

Of course, when I hear “vaginal tearing” and “6-foot-6 black guy” in the same sentence, I really don’t think it matters if it’s consensual or not, right?

In any case, Kobe’s case reminds me too much of Mark McGwire’s “Who wants to see some dingers?!” line from The Simpsons. America doesn’t care if you’re a first-class degenerate…as long as you’re a winner. God bless America!


5. President Bill Clinton

“I did not have sexual relations with that woman” became the worst lie by a President since Nixon told everyone he wasn’t a crook.

Clinton gave a whole new meaning to the term “oval office” and yet, somehow, this whole mess made Bill Clinton become more popular.

Honestly, nobody thought that a president could be more idiotic than Clinton…and then came George W. Bush.


4. Steve Phillips

If you’re a successful and widely respected baseball analyst, a guy who looks like Anderson Cooper with a goatee and a former general manager of the New York Mets, then you can probably aim a little higher.

But instead of burning his infidelity card on a home run, Phillips bunted with Brooke Hundley, who’s the kind of girl that makes you want to commit suicide when you wake up next to her after a night of binge drinking.

Hundley went so far as to write Phillips’ wife a confessional letter, and even stalked his sons on Facebook under a fake profile. Adds a whole dimension to “Facebook creep” if you ask me.


3. Tiger Woods

When my buddy, who is going to remain nameless, felt like he was getting the itch to cheat on his girlfriend this past weekend, he leaned back in his chair, gave himself a good stretch, and admitted to the boys that he “felt like becoming a Tiger tonight”…and I was too busy giggling like a little girl to condemn his behavior in any way. Thanks, Tiger.

Women have “cougar” and now we have “Tiger.” Maybe I should’ve just kept an entire golf theme throughout this list. It would’ve gone something like this:

10. David Letterman Plays Through His Own Staff
9. Senator Craig Putts From The Rough
8. Pitino Fixes His Divot
7. Jude Law’s Reverse Scramble
6. Kobe Bryant Hits 18-(Year-Old)-Holes
5. Clinton Interns Ball Washer
4. Baseball Analyst Chunks The Cabbage
3. Tiger’s Unplayable Lie

Yet even Tiger’s recent foul play couldn’t outrank him against the top 2 on my list…and I wasn’t about to ruin the surprise for you.


2. Hugh Grant

In 1995, if you were to ask anyone who the luckiest man in the world was, people would hands down have said Hugh Grant.

He was a media darling, a charming twit with a British accent who had just made an absolute killing with Four Wedding and a Funeral before exploding in Hollywood.

On top of that, he was dating one of the most beautiful women ever known, Elizabeth Hurley.

Yet, as Tiger proved, even the mightiest public charmers can fall flat on their faces and into the crotch of infamy.

Grant, for his part, fell into bed with a prostitute and was caught by the LAPD, and Hurley dumped him years later (allegedly amicably) after 13 years together.

Grant has since become the poster boy that, no matter how good you have it, you always want something else.

It can’t be truer when you could literally have had any woman you wanted, chose Elizabeth Hurley in her prime before anybody else even knew her, and then took home a whore who looked like a transsexual version of Oprah Winfrey.

Hugh Grant, you’re the consummate reason that modern women are constantly worried about infidelity in their own relationships. And it’s true—if a woman like Hurley couldn’t keep a man happy, who the hell can?


1. Prince Charles

Prince Charles married one of the most decent and lovely women we have ever known in Princess Diana.

He dumped her for Camilla, Duchess of Cornwall, and was so obvious about his affair that it practically drove Diana insane and caused a flurry of paparazzi to hound Diana, leading to her eventual death in a fatal car crash while paparazzi chased her down a street tunnel.

All the other guys on this list have been infidels on out-worldly levels, yet Prince Charles remains at the top of the heap because none of his fellow infidels actually behaved in such a deplorable manner that it caused their spouse to die.