Heartbreak No. 4: Britney Spears On MTV’s 2008 Video Music Awards

It’s nearly impossible to forget Britney’s disastrous 2007 Video Music Award-opening performance of “Gimme More,” which coincided with one of our most overpublicized celebrity breakdowns. Soon after, Britney’s people took charge, kicking out the strays (Osama Lufti, anybody?), getting her medication straight, and attempting to get her weave back on point. The plan, calculated by Britney’s on-again manager Larry Rudolph and her father Jamie, was for Britney to redeem herself at the award show this year. She wouldn’t put on one of her legendary VMA acts, but she would get back into the public eye, look pretty, and win a few awards.

Remember when Britney was the most famous person on the planet—when there was no actor or musician or personality who wouldn’t participate in anything with Britney? I do. So who did MTV pull out for Britney at the 2008 VMAs? Jonah Hill. Nothing personal, but he’s a human snooze button. The show opened with a stiffly acted, generally unfunny sketch, lit to reveal every kink in B’s extensions and layer of her foundation. Britney wasn’t back—she looked like a shell, trying her hardest to redeem herself by exchanging clichéd dialogue with a C-list comic actor. Something was missing, something important and perhaps not to be reclaimed. And that’s pretty heartbreaking.

80 ’08 (and Heartbreak)