15 Celebrity Cringe-Worthy Rock Bottom Moments

Celebrity and scandal go hand in hand and sometimes a celebrity can overcome and move on. Either their fans are forgiving, like with Michael Jackson, or it just takes a while and people just stop caring, like with Hugh Grant. But sometimes a celebrity does something so ridiculous that, for whatever reason, their career never really rebounds and for the rest of their lives, they’re going to be known as “that” person. These are the moments when they hit the lowest point imaginable, and they’re saddled with the fallout forever.

Danny Bonaduce Punches a Transvestite

Everyone likes a good celebrity sex scandal, but usually they involve infidelity or, at the very least, a hooker. Danny Bonaduce almost fit into that second category.

One night, while admittedly totally wasted, Bonaduce tried to pick up a prostitute. What he got was Darius Barney, a 220lb man dressed like a woman. How does someone make a mistake like that? Wasted.

Bonaduce says that as soon as he saw Barney in the light, he wasn’t so wasted that he couldn’t tell what happened, and he told Barney to get out. Barney demanded $40 for his time and effort so when the two got out of the car, Bonaduce did what any self-respecting, wasted man would do when confronted with a transvestite that outweighed him by about 70lbs, he sucker punched him. The result was probation for Bonaduce and the loss of his job at KKFR radio. And probably a story that Darius Barney still tells to this day.

OJ Writes a Book

Arguably OJ became more famous, or at least infamous, after his media circus of a murder trial, but man, did he take the cake a couple of years later when he tried to write a book about it. You may have forgotten Simpson’s “If I Did It,” a book that was supposedly a fictional account of how he would have killed Nicole Brown and Ron Goldman. It’s possible someone, somewhere, has had a worse idea. It’s possible.

After the entire human race choked in disbelief, protests sprang up, the publisher who OK’d the book was fired and a judge put the kibosh on the whole thing and awarded any rights to Goldman’s family, to help pay off the many millions still owing them in the civil suit they won against Simpson. This one act cemented it for anyone who might have held hope that OJ was really innocent that, innocent or not, the man is a complete jackass.

Ashlee Simpson Jigs

Arguably being a member of the Simpson clan means you have a lot stacked against you already in terms of credibility. With a sister who can’t tell fish from chicken and a father who likes to point out his childrens’ racks, things have always been rough, despite the fame. Still, the family as a whole got to experience an all-time low when youngest star Ashlee was doing her thing on Saturday Night Live and the audio track she was lip synching to got messed up, playing the wrong song. What’s a girl to do? Dance a horrifyingly awkward jig on stage and wait for producers to cut to commercial.

David Hasselhoff Gets Fired

In the last decade or so, David Hasselhoff has been riding a wave of kitschy popularity. People like him in a kind of mocking way, for his music career, for his drunken Youtube videos, for remembrances of Baywatch Nights, the most preposterous show ever. He even parlayed that into a gig co-judging America’s Got Talent. For a while.

Those aforementioned drunken Youtube videos were a part of Hasselhoff’s problem as apparently the Hoff has a severe issue with alcoholism. One that leaves him belligerent and difficult to work with. Reports from the show indicate Hasselhoff was either always drunk or hung over and entirely unpleasant to be around, so producers finally had enough and gave him the axe, removing a man whose music career is sustained solely by people looking for a laugh from a television show that typically plays out like a poor man’s American Idol with ventriloquists and magicians.

Ricky Martin Supports Golden Showers

You may not remember, but for a time Ricky Martin was insanely popular. Why isn’t he so popular anymore? Maybe he moved back into the Spanish language market for a spell, or maybe because back in 2005 for reasons that will probably never be adequately explained, Martin told Blender magazine that he really digs golden showers. You know, peeing on someone for sexual gratification? Yeah, that.

The interview was short and mostly unremarkable, save that when they asked Martin about what kind of porn he watched last he strayed into pee talk. The result, surprising to no one but Martin himself, was a whole slew of disgusted people and criticism directed at the singer and even the charity he founded, causing Martin to attempt to defend himself and his work while forever being unable to shake the image from people’s minds that he’s a pee fan.

George Michael Loves Men in Public

There’s a hilarious scene in There’s Something About Mary when Ben Stiller’s character stops at a highway rest stop and gets caught in a police sting as hordes of gay men run from the scene. The joke is that highway rest stops are havens for gay men trolling for anonymous sex. If you take out Ben Stiller and put in George Michael, you’re no longer in a movie, but real life.

Michael, who managed to still be famous even after being in Wham!, has been arrested for drug possession before, but in 1998 he was nabbed by an undercover cop for engaging in a lewd act. Which is to say Michael was doing a bit of pocket pool minus the pockets.

Having finally been outed as gay, Michaels seemed to spiral into depravity faster than you can jitterbug, getting arrested again for sex in a public park and admitting in interviews that he’s pretty content to troll for anonymous sex whenever the mood strikes.

Boy George the Kidnapper

So Boy George has always been a bit weird, but that seemed to be his gimmick. He was Lady Gaga in the 1980s. Things got weirder in 2008, however, when George apparently decided that holding people hostage would be a good course of action.

According to George, the victim in question, a male escort, had been stealing files from his computer. So George handcuffed him to a wall and investigated in the style of all great, sexually confusing detectives. Whether or not he found evidence of file stealing chicanery is somewhat secondary to the false imprisonment charges and ensuing media circus that allowed the world a new glimpse at the bald, skull-tattooed felonious George we never knew existed.

Tom Cruise Loses his Mind

You may not remember this, but Tom Cruise was a respected superstar once. He was Top Gun, and that was awesome. He made Days of Thunder, which was Top Gun on the ground. It was less awesome, but it didn’t make people wince. But then, one day, Tom Cruise found religion. Sorta.

Tom’s public involvement with the Church of Scientology pretty much ruined the man in the eyes of the public. He went from being easily one of the most bankable stars in the world to the butt of jokes that continue years later and have left his career tarnished.

The problems really got rolling when Cruise went on Oprah to announce his love for Katie Holmes, a woman most people who don’t watch angsty teen dramas had never heard of. While shouting and jumping around like a lunatic, it suddenly became clear that Tom Cruise was an odd duck.

In a whirlwind of horrible public appearances around the same time, Cruise compared psychiatry to the Nazi party, got into a verbal fight with Matt Lauer, trash talked Brooke Shields for just short of no reason whatsoever, made an ass of himself after being squirted by water in a practical joke, made a string of less and less impressive movies, culminating in a leaked Scientology training video that makes him look like he’s a near total madman who thinks he can cure disease and save the world with the power of his mind.

Michael Richards Can’t be Heckled

During his time on Seinfeld, Michael Richards was a comedy icon. Kramer had become a part of pop culture in the way characters like Bart Simpson and Lucy had. They still sell that velvet Kramer painting in some stores.

Post-Seinfeld Richards seemed to disappear for a while and then apparently started doing stand-up comedy. Bad move. If there’s one thing you need to have when it comes to comedy, it’s thick skin. People love to trash talk, insult and heckle. So when two hecklers in the audience to one of his shows wouldn’t shut up, Michael’s should have responded with some fast-paced zingers that would have got the audience on his side and against the hecklers. Hel, he could have just called them douchebags. Instead, Michaels opted to start shouting racial slurs at the two black men. Bad choice, Cosmo.

Michaels later made a kind of awkward apology on the Late Show with David Letterman but by then the damage was already done. On the upside, Michaels actually parodied the incident in an episode of Curb Your Enthusiasm in a way that was so tasteless it’s actually really funny.

Bald Britney Flies into a Rage

For a while there, Britney Spears was the biggest thing in music. Then, as she became more popular and people started being given more access to her personal life, it became clear she was remarkably ridiculous as well. Because seriously, Kevin Federline? The guy wore undershirts 9 times out of 10 and appeared to never bathe.

That aside, after years of public scrutiny and a couple of failed marriages and the pain of having to live with being responsible for some of the most gibbering bubblegum pop ever recorded, Britney snapped like a twig. And she shaved her head bald.

While a bald Britney isn’t the craziest thing you’ll ever see, a bald Britney attacking people with an umbrella is pretty much priceless. And because the intended victims were paparazzi, you better believe that was caught on tape.

Straight out of THX 1138, Britney rained holy hell down upon a paparazzo’s car after trying to visit her ex only to find him not at home. The camera catches many delightful angles that make her look a bit like a slimmed out Alfred Hitchcock on a bender.

Tara Reid Frankenboob

Party girl Tara Reid is still pretty much only famous for the American Pie films. And a show in which all she did was get wasted. And how, in real life, all she did was get wasted.

While most bad girl celebrities were busy “forgetting” to wear panties and accidentally get themselves plastered on the internet, Reid opted instead to take a classier path and showed off some boob. So far so good, right?

The problem here was that Reid has recently had breast implants and the surgery was done by an orangutan with some kind of palsy, if the pictures are any indication. Standing on the red carpet at some manner of formal event put on by P Puffy Diddy Daddy, Reid’s dress slips and she’s completely unaware that one scarred, misshapen boob is screaming to be euthanized in front of the cameras.

Kanye West is Kanye West

Like Tom Cruise, Kanye West has a career full of incidents you could point out as being pretty much preposterous. Unlike Cruise, West has been able to get away with it for a long time. Every time he said some egomaniacal thing, or performed some outrageously douchey act at an awards show, people shrugged it off. Until that last time.

At the 2009 MTV Music Video Awards Kanye apparently thought his ability to obnoxiously push people out of the way and say whatever he felt was still in full swing. So when Taylor Swift won Best Female Video, West figured he’d take her microphone, just to let her and the world know that while she’s good and all, she shouldn’t have won. West had gone from being a douche on his own behalf to being a surrogate douche for others.

In the aftermath, everyone capable of speech rained trash down on West, even President Obama called him a jackass.

Pee Wee wanks in a theatre

Paul Reubens was one of the most successful children’s entertainers of the 1980’s, even if he had an offputting sort of menace to him all the time. He was colorful and eclectic and kids dug that sort of thing. In fact, adults dug him too simply because he was so damn bizarre on TV and in film.

Then, in 1991, while visiting relatives, Pee Wee decided to visit a porno theatre. This is where police found him, spanking little Pee Wee, and arrested him because even though it seems counterintuitive, you can’t masturbate in public, even if it is a porno theatre.

The arrest brutalized Reubens’ career in ways few scandals had done to any celebrity before. He was roasted in the media, his show was canned immediately, even his toys were pulled off of store shelves. Reubens retreated from the public eye, unable to escape stigma of what had happened, and hung up Pee Wee’s bowtie almost for good after a small number of public appearances around the same time of the arrest. It wasn’t until 2006 that Reubens would return to the character, a full 15 years later of being almost completely out of Hollywood.

Tiger Woods Drives into a Tree

When it comes to golf, Tiger Woods is, or at least was, the King. He was the game’s Babe Ruth, its Michael Jordan. He could do no wrong. But that was just on the fairway.

Off the fairway he had a bit of a reputation as being somewhat standoffish, but not many people were prepared for the explosion that happened in 2009 when word hit the street that Tiger Woods apparently has to have sex with everything that has a vagina that comes within 10 yards of him. And how did the story break? With Tiger driving right into a tree amidst rumors his wife was beating him with a golf club.

Though the Tiger scandal is an ongoing, long and multi-faceted thing, it was all set off by the mysterious circumstances around Tiger’s car accident. He ran into a hedge, a fire hydrant and a tree, then refused to talk to the police. Then released a statement saying it was private, which is much like saying “yes, the rumors are true, I hump many woman” and from there it all went downhill for Tiger as woman after woman came forward claiming to have had an affair with him.

Tiger lost endorsements left and right, he retired from golf, word leaked one of the women had nude photos of him and his wife is now going around without her wedding ring on any more. Things are not looking good for Tiger, however this CG reenactment from Taiwan does make them look intense.

Dustin Diamond does the Dirty Sanchez

Dustin Diamond played Screech on the kid’s show “Saved by the Bell” back in the 1990’s. He was the creepy weird, kid. In real life, he became a creepy, weird adult. How creepy and weird? He made a sex tape featuring himself, two women, and the Dirty Sanchez.

Inexplicably thought to be a PR stunt, the very idea of Screech giving someone a dirty sanchez is terrifying. For those who don’t know, the dirty sanchez is something you’re better off not knowing. But if you must know, even though there’s no non-horrible way to describe it, it involves using one’s penis as a pen to draw a mustache on another human. For this to work, one must engage in anal sex prior to the drawing to allow for there to be something on the penis with which to draw, if you follow us. Feel free to go weep or vomit.

The tape got huge media exposure, mostly because it’s one of the most awful things that has ever existed. It’s unclear if it actually helped his career in any way, since apparently he’d been suffering through a lot of debt and arguably couldn’t have had his career in worse shape, but it’s certainly going to be an awful monkey on his back for the rest of his days.

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