In honor of Tiger Woods' unprecedented fall from grace, here are the all time dumbest celebrity cheaters. The "smartest" leads it off, then going down right through the bottom of the barrel.

Hugh Grant

Somehow, Hugh Grant ends up as the smartest man on this list. Yes, he cheated on Elizabeth Hurley with a prostitute. Yes, he got arrested for cheating on Elizabeth Hurley with a prostitute. Yes, he decided the best time to cheat on Elizabeth Hurley with a prostitute was while he was touring to promote his upcoming film, Nine Months. So why is Hugh Grant the "smartest" man on this list? Ironically, it's because he cheated on Elizabeth Hurley with a prostitute.

The other men included here have cheated with coworkers, nannies, and random club-hopping attention-whore types. Hugh Grant actually had the presence of mind to seek out a prostitute, someone who views sex as a normal daily occurrence. He probably figured she'd get in the car, go through her routine, and he'd never see her again. The serious flaw in the logic, of course, is that he was a major celebrity in the process of doing a media tour, so even if the cops hadn't busted him, the girl probably would have realized who he was and sold the story to the tabloids.

Elizabeth Hurley © Courtesy PR NewsFotos

Flawed thinking is still thinking, though, and at least Hugh Grant was trying. That's enough to crown him stupid on a list of all-out morons.

Brad Pitt

When Mr. and Mrs. Smith started filming in 2004, most of the media focus wasn't on the movie itself, but on Brad Pitt and Angelina Jolie. How would they work together on-screen? Would their relationship be strictly professional? Was there a chance his spiky hair could accidentally poke her freakish lips and burst them?

At least one of those questions was answered in 2005, when Jennifer Aniston filed for divorce. Though Brad Pitt vehemently denied an affair, he did admit to falling in love with Angelina Jolie on the set of the movie, which is one of those male technicalities that women often have problems with. Perhaps Brad Pitt created his own little world where adultery only means sex, but on this planet wives tend to get a little upset when you fall in love with another woman while married. They're funny that way.

Image © Albert L. Ortega / PR Photos

Moving past semantics, though, Brad Pitt was dumb for having an affair with a coworker. That kind of thing is hard enough for normal people to keep quiet, so what hope did a two-time "sexiest man alive" really have? People are eager to share that kind of information even without tabloid encouragement. Brad Pitt may have gotten himself a woman that most every man wants, but he sure went about it a stupid way.

Jon Gosselin

Jon Gosselin (and his whole family, really) was first the beneficiary, and then the victim of, our nation's obsession with reality TV. This is a man who the general public really has no right to care about. His only marketable talent is a freakish virility which, at the moment, he probably wishes he didn't have.

Whether or not he should actually be a celebrity, the fact remains that he is a recognizable figure. More importantly, the reason he is recognizable is because he agreed to live his life under constant surveillance. How the hell did he plan to have an affair without anyone noticing?

The general idiocy here is compounded by how Jon Gosselin is exponentially more dirtbaggish than anyone else on this list. Sure, some men cheat on their wives, or walk out on a wife and a kid, but he betrayed his wife and EIGHT children. The eight children that made him "famous" in the first place. His image has been completely destroyed, and rightfully so. The only reason he's not number one is that as a kind-of celebrity, he didn't have that far to fall.

And really, why not just file for divorce? The marriage had obviously fallen on bad times, anyone watching the show could see it on his face. Why not just end it, instead of putting eight kids through all this?

Eric Benet

Eric Benet claimed that sex addiction led him to sleep with an ex-girlfriend only days before accompanying his wife, Halle Berry, to the Oscar ceremonies in 2002. Whatever the reason, his infidelity is as mind-boggling now as it was then, and not only because he cheated on the still respected, pre-Catwoman Halle Berry.

To put it kindly, Eric Benet was playing way out of his league in 2002. Sure, he was a nice singer, but he somehow managed to get with Halle Berry, at the peak of her career, when she was riding the wave of X-Men, Swordfish, and Monster's Ball popularity all the way to an Academy Award. This was a woman who played a badass superhero, a badass counter-terrorist agent, and who managed to keep herself from vomiting while doing a sex scene with Billy Bob Thornton. She was at the forefront of Hollywood. And he was…Eric Benet. Kind of like Lenny Kravitz, but slightly more well-groomed and without the benefit of loud instruments to drown out his annoying voice. That's the man who decided he could do better than Halle Berry. Dumbass.

Jude Law

Look at pictures of Sienna Miller and Daisy Wright side by side, and try to logically determine which one was the fiancée, and which one was the mistress. Now reverse your choices, because unfortunately, Jude Law is not a logical man. How else can you explain an affair with Daisy Wright while Sienna Miller's waiting at home? It's baffling.

Beauty is in the eye of the beholder, though, and perhaps Jude Law can't be judged too harshly for something that may be his personal preference. He can be judged, however, for the fact that Daisy Wright was his children's nanny. Maybe he was trying to one-up Brad Pitt - he figured any idiot can sleep with a co-star, but it takes a real imbecile to start an affair with an employee. So many things can go wrong, it's almost impossible to keep track of: She could get fired, she could get offended and overreact, she could demand a raise - and that's assuming normal circumstances. Throw in the flurry of cameras that follow Jude Law around, and he should have known he didn't stand a chance.

Then, of course, he decided to go the classy route and blame Sienna Miller for getting cheated on. So see, he's not only unfaithful, he's also a douchebag. What's not to like?

Tiger Woods

What exactly could have been going through Tiger Woods' mind? His wife is the epitome of what most men spend a lifetime in pursuit of: Blonde, Swedish, and a model. That's the holy trinity of male fantasies that aren't supposed to come true. If somebody manages to get even two of those three, they're pushing their luck. And Tiger Woods has the nerve to think that he can do better? What exactly was he going to trade up to, a blonde Swedish model gymnast? Ballet dancer? Superhero?

Even forgetting the fact that Tiger Woods cheated on Elin Nordegren (which is INEXCUSABLE), it's astonishing how stupid he was about it. Over 300 text messages? Really? Beginning voicemails with "Hey, it's Tiger?" Is he just dumb? It's not like his name is Steve, or John. There is no one else on this planet that is identified as Tiger. He's it! Why even leave the message in the first place? Why not spend some time thinking of a decent cover story.

I don't know what's more upsetting, the fact that Tiger Woods is a cheating scumbag, or the fact that he's the dumbest cheating scumbag that ever existed.

Story by Jose Flores

Starpulse contributing writer