Paul Reubens
Paul Reubens will always be Pee-wee Herman — that childlike, bow tie-wearing character with the infectious laugh that we fell in love with on the surreal Pee-wee’s Playhouse and in the hysterical Pee-wee movies. That’s why it was such a shock when Reubens was arrested for public masturbation in 1991 and basically vanished off the face of the planet until fairly recently. He’s resurrected his image — a persona Reubens always went to great lengths to keep squeaky clean — and as adults we can forgive, forget, and accept Pee-wee’s darker side, even if Reubens’ career has never truly recovered from the incident.
Frank Miller
Comic book legend Frank Miller brought us Daredevil, Batman: Year One — the 1987 story arc that the successful Christopher Nolan Batman trilogy is based on — the Sin City series, and other fan favorite titles many grew up with. Since 9/11, however, Miller has acted weird, coming across as a kooky conspiracy nut that hates everyone. His truly offensive 2011 graphic novel Holy Terror (dubbed anti-Islamic propaganda by most audiences) further proved Miller’s inability to differentiate between a few billion peace-loving people and the radical fringe. He also took aim at the Occupy Wall Street movement, calling protestors “a pack of louts, thieves, and rapists, an unruly mob, fed by Woodstock-era nostalgia and putrid false righteousness,” further stating that “these clowns can do nothing but harm America.”
Hulk Hogan
Back when we still kind of understood what the hell was happening with the World Wrestling Federation, Hulkamania was a thing, and the muscle-bound star was the face of the industry and a hero for kids who imitated his Doublehand Choke Lift and Strong Clothesline. Then he became a reality TV star (revealing the icky drama of his family life), suffered numerous health problems, became suicidal, and was the subject of a sex tape released earlier this year. Darren Aronofsky’s The Wrestler — about a washed-up champ — depressed us for days. For Hulk fans, watching the real-life version hasn’t been easy either.
Melissa Gilbert
Laura Ingalls Wilder was a frontier heroine on Little House on the Prairie, but her life spun out of control after several failed relationships and the tragic loss of a child. She battled alcoholism, drug abuse, and became a late-night infomercial queen. She’s made TV appearances here and there, including on Dancing with the Stars, but the biggest moments of her career are still in reruns.
Macaulay Culkin
Culkin rose to fame playing witty tyke Kevin McCallister in the Home Alone series, but since retiring from acting at the ripe old age of 14 (around the same time he had a falling out with his parents), he’s been a bit of a mess. We’ve been curious about his visual art career, but then horrible photos like these keep popping up with headlines about devastating drug abuse.
Lindsay Lohan
From freckle-faced Disney cutie in The Parent Trap, to teen star in Freaky Friday and Mean Girls, Lindsay Lohan was an ambitious young actress most girls could relate to and her star seemed to be on the rise. Since the early days of her career, it’s no secret that things have taken a turn for the worse, and while Liz & Dick (and probably The Canyons) looks absolutely ridiculous (we’ll probably, maybe still totally watch them both), we continue to hope Lohan’s days of ankle bracelets and mamma/daddy drama are behind her. She was in that new R.E.M. video directed by James Franco, so… maybe?
Elizabeth Berkley
We liked Berkley better when she was sharing her feminist viewpoints on Saved by the Bell and calling Slater a macho pig, instead of thrashing around like an epileptic dolphin in Showgirls. Her teen advice and book website shows promise.
Kurt Cobain
The Nirvana frontman was gifted with the ability to transform his personal trials and tragedies into universal truths. Struggling through an addiction and numerous health problems, Cobain was frustrated by the media and uncomfortable in his own skin as the spotlight took hold. He hadn’t “felt the excitement of listening to as well as creating music… for too many years now,” and soon after the voice of a generation was gone.
Michael Jackson
Some people could ignore the King of Pop’s Wacko Jacko side — which included bizarre media stunts, hyperbaric oxygen chambers, and botched nose jobs — but for others, watching the energetic star allow his weird ways to veil his undeniable talent was heartbreaking. Then there were the child sexual abuse allegations. Even in death, Jackson’s career with the tabloids continued as his personal physician was convicted of involuntary manslaughter.
Corey Haim
Everyone’s favorite Corey seemed like the cutest, most innocent boy next door, but his problems with drugs and alcohol started when he was only 14-years-old, drinking beer on the set of Lucas. His self-described breaking point was at just 16-years-old and he was never able to recover from his past despite giving it a go with reality show The Two Coreys (with longtime pal Feldman) and other brief appearances, like in Crank: High Voltage. After his death — ruled to be from natural causes — the Academy Awards and Annual Screen Actors Guild Awards added insult to injury by omitting him from the in memoriam tribute montage.