Sid Vicious & Nancy Spungeon
Punk groupie Nancy was stabbed to death with Sid's knife, but to this day no one knows for sure who wielded the blade. Five months later, Sex Pistols bassist Sid left his mother a suicide note and overdosed on heroin. The film Sid & Nancy turned them into popular icons of drugged-out self-destruction.
Ike & Tina Turner
Ike, in his own words: "Sure, I've slapped Tina...There have been times when I punched her to the ground without thinking. But I have never beat her."
Charming.
Madonna & Sean Penn
Lit match, meet dynamite fuse. These two didn't even seem like a good idea at the time. He was charged with felony domestic assault in 1988 and they ended their four-year marriage in 1989.
Robin Givens & Mike Tyson
The yearlong marriage between the star of 1980s sitcom Head of the Class and the heavyweight champ was fraught with allegations of greed and spousal abuse.
Courtney Love & Kurt Cobain
Heroin, clinicial depression and rock-star drama doomed this pairing, but the two did successfully produce adorable Frances Bean Cobain.
David Gest & Liza Minnelli
So many friends of Dorothy in this photo...
Tommy Lee & Pamela Anderson
The marriage of the Mötley Crüe drummer and the Baywatch pinup is largely remembered for launching one of the Internet's first celebrity sex-tape frenzies.
Kim & Marshall Mathers
He's lyrically murdered her once, in the six-minute rap "Kim," and divorced her twice. We think Mr. Mathers needs to get out of Detroit and start mixing with a better class of lady. You can't just stay hung up on your high school girlfriend forever, you know?
Brandon Davis & Mischa Barton
The O.C. star and the oily oil heir were tabloid staples during their troubled year together, as rumors swirled of drug use and general debauchery.
Shanna Moakler & Travis Barker
The Blink-182 drummer and the former Miss USA continue to be in an on-again, off-again relationship that seems largely devoted to toggling their MySpace statuses between single and married.
Amy Winehouse & Blake Fielder-Civil
He's spent time in jail and her most famous (and admittedly catchy) song would seem to be an autobiographical refusal to take her drug-addicted self to rehab. At first their dysfunction was the gimmick that got them ahead, but now it's just plain sad.
Pete Doherty & Kate Moss
Not that the superskinny supermodel was ever anybody's saint, but getting in bed with this self-admitted junkie seemed to turn her to the dark side. Ick.
Lindsay Lohan & Samantha Ronson
We don't know what these two crazy kids are really into—heck, they might just be high on life—but their mindless shenanigans are a fairly pathetic way to squander their youth. Grow up, you silly, silly little girls!
Jon & Kate Gosselin
She's a controlling bitch. He's a douche. Don't believe us? Read the news for yourself.
Whitney Houston & Bobby Brown
Whitney's being all grown-up now and taking responsibility for her actions, but the truth is that we'll always blame that dang Bobby Brown for destroying her life.
Want to check out some other celebrity nogoodniks? Get E! Online's What a Douche gallery.