1. Pee-wee Herman: Back in 1991, Paul Reubens walked into a movie theater as one of children's TV's most popular and beloved entertainers. He walked out an entertainment pariah. The theater, as it happens, was showing a triple feature of porn and Reubens apparently decided to loosen his red bowtie more than he should've that day: cut to his headline-grabbing arrest for indecent exposure. He pleaded no contest and more or less laid low for about a decade. Right when he was aiming to make a comeback, with 2002's "Blow," he was arrested a second time, when cops found photos of nude teens (he said they were vintage erotica) around his L.A. home. Sure, he's appeared in other projects since and even recently put on a Pee-wee stage show, but has never reached his pre-scandal heights of fame. And when your name is still an automatic punch line 20 years later, you haven't won.
2. Roman Polanski: Sure, Roman's big screen projects continue to defy logic and morality and attract both critical laudings and A-list stars (call it the Woody Allen effect), but there's something about having sex with a drugged-up 13-year-old girl that just sort of has a way of following you around your career, you know? Polanski found that out back in 2009, when instead of picking up a lifetime achievement award at the Zurich Film Festival, he was picked up and taken into custody on the then 32-year-old charge he had fled the U.S. to avoid. He was put into house arrest and sent Hollywood into disarray between "Free Polanski" supporters and those who had common sense (shout-out to Kirstie Alley!). And seeing as how he's still not welcome in this country, we'd call that a fail.
3. R. Kelly: Look, we know R. Kelly was found not guilty on all 14 counts of videotaping himself having sex with an underage girl (a 14-year-old girl, for the record). We know that he's had his share of hits in the years since the allegations first came up (however laughable the operatic and neverending "Trapped in the Closet" was, it received ridiculous amounts of radio and airplay). But, fair or not, when it takes you six years to fight a kiddie porn case, that's what you're going to be remembered for. Besides, when was the last time you heard R. Kelly's name and not smirked? Case closed.
4. Jesse James: He's found love again. Which, you know, more power to him. He found someone willing to publish his memoir. And even more people who allowed him to promote it on TV. It sold in decent numbers. And yet...when you think Jesse James, do you think, "Man, what a comeback that guy made!" No. No, you don't. Some things you cannot unsee, and a man in a Nazi uniform giving a "heil" salute is one of them. Besides, no one breaks the heart of America's sweetheart and is allowed back into the A-list. Except for maybe Brad Pitt.
5. Michael Jackson: Yes, he was the King of Pop. Yes, his contribution to music will never be forgotten or perhaps even superceded. But he also failed to ever make the same impact on the world, musically or otherwise, as he did before his neverending stream of child-abuse allegations and trials. Accusations first surfaced in 1993. A media circus followed. He infamously went to trial on a new set of allegations in 2005. He was acquitted, sure. But he was never the same.
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