(FORTUNE Magazine) – Supermodel Kate Moss's public dismissal from campaigns with H&M, Chanel, and Burberry after reportedly being photographed using cocaine is the latest reminder of a simple truth: Arranged marriages between brands and celebrities are inherently risky. In the post-O.J. world, companies are tougher about enforcing morals clauses. According to Peggy Walter, who negotiates contracts at Leo Burnett, today it's standard practice to sign a celeb only after an extensive background check. But accidents still happen. Below, a short history of celebrity endorsements gone wrong. -- Eugenia Levenson

OOPS!

NOT WHAT'S FOR DINNER

1987: The Beef Industry Council enlisted Cybill Shepherd to expound on her beef cravings for the "Real food for real people" campaign, but the move backfired when Shepherd admitted in public that she didn't eat meat.

OUCH!

BAD INFLUENCE

1988: Anheuser-Busch anchored its Michelob campaign with Eric Clapton's remake of "After Midnight" only to have the rock star tell Rolling Stone that he was battling alcoholism when he made the commercial and was in a detox facility by the time it came out.

YIKES!

SCRAMBLED EGGS

1989: Long before he ignited a steroid controversy with a tell-all book, slugger Jose Canseco was fired from his job as spokesperson for the California Egg Commission following his arrest for possession of a handgun.

DUH!

LOSE THE JUICE

1994: Hertz capitalized on O.J. Simpson's mass appeal with ads that first aired in 1975--and was stuck with the mental link after Simpson was charged with a double homicide, then tried and acquitted on national TV.

YIKES!

UNHAPPY MEAL

2001: Kobe Bryant lost millions in endorsement deals with McDonald's, Sprite, and Nutella after he was charged with sexual assault. Charges were later dropped.

OUCH!

SPILT MILK

2004: The "Got milk?" campaign pulled ads with twins Mary-Kate and Ashley Olsen when Mary-Kate checked into a treatment facility for a "health-related issue" that some publications reported as an eating disorder.