Lindsay Lohan has been on a slide for almost a decade now, so it's kind of adding insult to injury to put her on this list, but let's be frank: posing for Playboy means the dream is officially over. Lohan's perfectly-shaped fun bags won many a heart in her prime, but ten years of cocaine and Twitter have ravaged the former Mean Girls hottie. Even with the incredible airbrushing talent that Playboy brings to the table, the 25 year old actress still looks like she's in her early forties. Way to ruin tits for me, lady.