Top Celebrity FAILS of the Decade

Urbandictionary.com defines a FAIL as “a glorious lack of success,” and we think that’s pretty spot-on. For to FAIL isn’t to just make a mistake: a true FAIL is a screw-up of magnificent proportions, the stuff legends are made of.

And who’s more capable of making monumental mistakes than the insipid celebrities that populate popular culture? Today’s disposable stars, with their spectacular rises to fame, are just as destined to come crashing down in an equally spectacular fashion. Below we’ve collected the five from the decade that we felt truly epitomize the celebrity FAIL.

1) Kobe Bryant and His $4 Million Dollar Screw-Up

This only happened six years ago? We have such short attention spans, don’t we? Kobe Bryant, arguably the most famous basketball player in the world, had an affair/possibly raped a 19-year old hotel employee in 2003. To get out of hot water with the missus, he had to buy her a $4 million dollar diamond ring, which she sported at his public apology. Why did Kobe want his wife back so badly? Three words: No. Prenuptial. Agreement.

2) Ashlee Simpson’s Entire Existence, but mainly her SNL performance

httpv//www.youtube.com/watch?v=SVA51sgBb3I

We will never get tired of this, ever. Ever! It combines everything great about a celeb fail: demonstration of an unlikeable personality (she blamed everyone but herself), getting caught red-handed, and the undeniable laying bare of a total hack. Bravo, Ashlee! You brighten our day.

3) Eliot Spitzer’s Hilarious Affair

Okay, we know a New York governor is stretching the definiton of celebrity, but Spitzer, a rising star once vetted as a possible running mate of Barack Obama’s, had the magnetic personality and chutzpah to qualify; that is, until he was discovered to be using state funds to have an affair with a Jersey callgirl named Ashley Dupre. What makes it a hilarious fail? Revelations that Spitzer refused to wear a condom when having sex with a prostitute while insisting his dress socks stay on. That there’s a FAIL, buddy.

4) Lindsay Lohan and Naptime

We all know Lindsay has a bit of an unfortunate reputation. And we feel a little bad. But, as one minor celebrity told us once, the paparazzi only follow those who want to be followed (think about the megastars you never see in US Weekly.) So don’t feel too bad. Look at her, passed out in a car like a drunk toddler! Point and laugh! From the gut now!

5) Tiger Woods Pissing All Over His Career With Glee

Alright Tiger! You made it on the list, with only a couple weeks before the end of the decade! We always suspected your life was too damn perfect. Glad you weren’t satisfied with everything the good lord gave ya. At press time, Tiger’s been given an ultimatum by that supermodel wife of his: golf or me. Either way it goes, you get FAIL of the decade, sweet Tiger!