The Shadiest Celebrity BFFs

Have trust issues? Try being famous for a day. In the entertainment industry, there's a very fine line between a bestie and a detestie. Is your personal assistant standing by your side because you're paying them, because they truly care, or because it's the perfect place to plot an attack? 

Is Gwynnie at your bungalow whipping up a fresh batch of her world-famous Morning Smoothie because she truly wants to hear you reminisce about Beetlejuice, or because she can't wait to get her quivering hands on that Shakespeare In Love script you left on your Industry West coffee table?  

From cherished childhood buddies selling private baby photos, to famous friendships that fantastically flamed out, here's a roundup of the shadiest shenanigans to emerge out of Hollywood, the music industry, and beyond. Let this be a lesson to you: In the world of showbiz, it's wise to keep your friends just as far away as your enemies, because more often than not, they're one and the same. 

Ryan Reynolds: Betrayed by one of his oldest and dearest

All the abs in the world couldn't save Ryan Reynolds from being cheated by a close friend. In 2015, the Deadpool star told GQ a personal story that will sully whatever lofty views of humanity you might have left. 

One of Reynolds' friends growing up — someone he'd known for the better part of his life — "had been shopping pictures of my baby around," he said. At the time, the tabloids were in a frenzy about Reynolds and his wife, actress Blake Lively, having successfully spawned. Photographic evidence of the bundle of joy was in high demand. 

Reynolds describes the revelation about his pal hitting him "like a death" and "one of those devastating things to find out." He told GQ he summarily stamped out the friendship during a "pretty strongly worded conversation." The friend's motivation allegedly boiled down to money. "I don't think he thought he would ever be caught," Reynolds said. "But it's a pretty narrow group of people that I would send photos like that to." 

Around the same time, Reynolds was run over by a paparazzo's car. He figures the driver was also trying to get his hands on one of those coveted baby pictures. Ultimately, the actor found the whole situation "shocking." He told GQ, "The whole thing becomes so absurd that all you can do is laugh about it and just go, 'This isn't the real world. This isn't how real things work.'"

Lindsay Lohan's bestie sold her list of lovers

Do you keep your "list" in a safe place? We recommend it, lest you wind up like Lindsay Lohan, gutturally sobbing about betrayal after having a list of her romantic conquests published by In Touch — who published it in two parts, like an adventure serial.

"That was part of my [time at] Betty Ford," Lohan confessed during her OWN docuseries (via E! Online). "It's step number five ... or step number eight. It's your sexual inventory. That was in my Betty Ford book." Lohan might be confused here, since step five is "be honest about your mistakes" and step eight is "make a list of the people you hurt." Then again, if a friend stole our list and sold it to the a tabloid, we'd be out of it, too.

Lohan suspects this ex-friend pilfered her intimate inventory while helping her move out of the Beverly Hills Hotel. "All of my books from [Betty Ford] were in that [room]. So, someone took a photo. Pretty sure I know who it is," Lohan said. 

For the record, the actress is not embarrassed by any of her celebrity hookups with handsome, wealthy men. "I don't care about me in that situation," she said. "I care about the people that are involved with other people because it's really unfortunate and disrespectful."

Is it in bad taste to name names? According to copies of the list obtained by E! Online, they include Justin Timberlake, James Franco, and "Zack Effren" [sic]. Is that shady?

Amanda Bynes' buddy capitalized on her mental breakdown

From the Department of New Lows: While Amanda Bynes was having a host of mental problems, someone in her circle — who Bynes deeply trusted — sold a highly private and very sensitive videotape to TMZ to make some quick cash. The footage, immediately splashed online, features a visibly distraught Bynes saying she's going to "murder" her father ("I want to literally, like, lead him into a ditch, and I haven't decided how I'd want to murder him ... nothing would give me greater pleasure than slitting his throat.")

After the entire civilized world had ingested the meltdown, Bynes issued a statement (via Access Online): "I'm sorry I trusted people who clearly were not my friends and capitalized on my illness," the statement said. "I am doing my best to get better. I am truly sorry for the statements I made. I am sorry for any pain I caused my family and others."

What she's probably really sorry about: not carefully vetting her small circle of friends. "I never expected others to take advantage and profit from my condition," she said. "I'm disappointed with those who lulled me into a false sense of security only to find out they really are only interested in selling my privacy to the media."

GwyNona: never meant to be

As Hollywood lore goes, there was a time in the '90s when two impressionable actresses named Gwyneth Paltrow and Winona Ryder were Tinseltown's most twinkly BFFs, creating Amazing Superfriend memories wherever they hung their Ellen Christine hats.

But it's a story of friendship torn asunder, reportedly because Ryder left a copy of an unproduced script lying around her well-appointed home, where prying eyes could find it. The script? Something called Shakespeare in Love. The prying eyes? Allegedly, they belonged to Gwyneth Paltrow, who went on to win an Oscar for her role in that fateful film.

And there's more: According to the Daily Mail, Gwyneth wrote a blind item for her airy blog Goop that contained a not-so subtle jab at Ryder: "Back in the day, I had a 'frenemy' who, as it turned out, was pretty hellbent on taking me down. I restrained myself from fighting back. I tried to take the high road. But one day I heard that something unfortunate and humiliating had happened to this person. And my reaction was deep relief and happiness." Hmm...

In 2013, the National Enquirer suggested the bad blood had not yet dried: "Those comments were a huge embarrassment for [Ryder]," a source said.

During an interview with Howard Stern, Paltrow swears absolutely none of this is true and we should all get a life and find our own backstabbing frenemies. "That's an urban myth," she said (via The Huffington Post). "I swear to God I did not, I'm raising my right hand on the Bible. I swear to God."

And God did "Tsk-tsk."

Paris Hilton's poisonous friendships: a secret history

Who'd ever suspect personal relations with Paris Hilton could be so slithery? Take her lifelong frenemy Nicole Richie. One minute, they're having the time of their lives, chillaxing outside The Lounge Club in matching denim suits. The next, sources are tripping over one another to let People know the relationship is on the skids: Richie's supposedly jealous about all the media attention lavished on Hilton.

In 2005, Hilton demonstrated that the best way to shade a former BFF is to do so via an official statement. "It's no big secret that Nicole and I are no longer friends," she announced cryptically, inspiring wild speculation from the tabloids. "Nicole knows what she did, and that's all I'm ever going to say about it." In retrospect, Hilton probably regrets not mass-producing "Nicole knows what she did" visors and half-tees.

But Richie didn't have it nearly so rough as another of Hilton's childhood friends: a certain Kim Kardashian. As Teen Vogue reported, that friendship was forever/temporarily tarnished when Hilton confessed she wouldn't want a backside like Kardashian's because it "reminds [her] of cottage cheese inside a trash bag." Evocative!

Apparently, Kardashian and Hilton are on good terms for now, with Hilton having "a lovely evening" at Kardashian's Christmas party in 2016. The calm before the next tongue-lashing? We wouldn't be surprised, for such is the nature of the modern-day frenemyship.

Drake Bell and Josh Peck called the whole thing off

The day Drake Bell announced his friendship with Josh Peck had hit the bricks, fans of Drake & Josh woke to a shattered world. One day, Bell happened to be casually flicking through his Instagram feed when he discovered a cache of Peck's giddy wedding photos. He stared aghast as they spilled across his screen without warning. Wedding photos. That Bell wasn't in. Because he hadn't been invited. To Josh Peck's wedding. (At least, that's how we're assuming it went.)

One thing is certain: Bell wigged, firing off a condemnatory Instagram screed. "When you're not invited to the wedding the message is clear," he declared. "True colors have come out today. Message is loud and clear. Ties are officially cut. I'll miss you brotha. Loyalty is key." (Okay, we get it.)

Fortunately, this particular tale has something of a happy ending: The former Nickelodeon stars have reconciled. "You know, it's like sibling rivalry for a minute," Bell told Entertainment Tonighin 2017. "But no, I mean we've gone through every up and down that you can think of that two guys can go through." 

The stars even briefly reunited for the short-lived series Grandfathered and got along swimmingly. "Man, we fell right back into it," Bell told AOL in February 2018. "I'm like 'Dude, I told you there's something there between us' ... It's once in a lifetime in this business. It's a Martin and Lewis, it's an Abbott and Costello ..." And occasionally, it's a Charlie Sheen and Chuck Norris.

​Denise Richards and Heather Locklear torched their friendship over… Richie Sambora?​​

Is it better to have lost your friendship to Heather Locklear than to have never loved Richie Sambora at all? That's a question actress Denise Richards must ask herself often. 

According to Complex, Bon Jovi guitarist Sambora and Melrose Place star Locklear filed for divorce back in 2007, back when Locklear's former bestie, Denise Richards, came sweeping in from some exceptionally glamorous movie set and began her own sexy adventure with Sambora. (Please note Richards had recently split with former husband Charlie Sheen for being Charlie Sheen.)

"I was no longer friends with Heather months before Richie and I got together," Richards assured a concerned Redbook scribe in 2008. "I don't want to say what caused the split, but she and I weren't even speaking then." But then Richards throws us a few shady morsels, because she can: "If Heather and I had been friends at that time, I would never have crossed that line. But we weren't. The friendship was not salvageable, and in the beginning Richie and I just talked as friends because we were dealing with similar situations."

The Daily News reports things got very peculiar when an enraged Locklear parked near Richards' home and began blasting "Livin' on a Prayer" at an ear-bleeding volume like some sort of savage. 

Shady stuff, but perhaps a blessing in disguise: Anyone who'd blast "Living on a Prayer" outside your home was never truly your friend.

These days, John Cusack and Jeremy Piven say nothing

Can you imagine anything less savory than actors John Cusack and Jeremy Piven being best buds? How about John Cusack and Jeremy Piven as mortal enemies and rivals? 

In 2007, The Associated Press (via The Washington Post) reported Piven's buddy was having a hard time accepting his friend's success following Entourage. (The two met at Chicago's Piven Theatre Workshop, owned and operated by Piven's mom and dad.)

"No comment," sniped Piven, when asked how Cusack was behaving toward him. "I mean, you could fill in the blank, I bet." Later in the interview, Piven lamented the Say Anything star's attitude: "I was always proud of him, and I was always in his corner ... It just says so much about a person if he has space for other people's success." And, in case that didn't quite drive the point home, Piven takes pains to spell out his main grievance: "I was raised on [a] spirit of collaboration. ... You start getting into trouble in life when you start comparing and contrasting your life to anyone else's. You don't win when you do that."

In response, John Cusack bravely came to John Cusack's defense. When People asked if he was jealous of Piven, he responded: "It's quite the contrary. I am very happy for Jeremy. I wish him the best and I always have." That's sweet ... except you don't wish anyone "the best" unless you're planning to never see them again.

Fifth Harmony mega-dissed Camila Cabello

There's a reason Camila Cabello's debut solo album is titled The Hurting, The Healing, The Loving. Before and after her departure, the drama with her former Fifth Harmony bandmates was off the charts. According to The New York Times, a statement sent out in 2016 by the remaining four members of the group blindsided Cabello: "We had to begin to formulate a plan and constructive path for Fifth Harmony to move forward, beyond Camila," the group said.

Cabello retorted on Twitter: "The girls were aware of my feelings through the long, much needed conversations about the future that we had [during] the tour."

That friction reportedly had everything to do with her collaboration with Sam Mendes in 2005. Following that project, Cabello's bandmates allegedly iced her and communication broke down. "It became clear that it was not possible to do solo stuff and be in the group at the same time," she told the Times.

Following Cabello's departure, the remaining members of Fifth Harmony pulled a bizarre prank during their 2017 MTV Video Music Awards performance: one of five performers onstage was unceremoniously yanked off her pedestal and plunged into oblivion. 

"It definitely hurt my feelings," Cabella told the Times. "I was just like, 'What? Why?'" Because they're shady ladies, Cabello.

"I feel with a friendship you think it's going to last forever," Cabello told Flaunt in 2017. "You start to consider that person like your family and so you don't see an end to that. So, when it's like a shocking or abrupt ending, that's worse."

Being pals with Katy Perry sounds positively perilous

Multiple reports suggest there are easier things in life than being BFFs with Katy Perry

Exhibit A: her falling out with Taylor Swift, who is admittedly no walk in the park herself. According to Teen Vogue, bad blood started spilling when Perry allegedly hired some of Swift's backup dancers out from under Tay. (Left Shark? You decide.) Perry addressed the beef (that apparently inspired "Bad Blood") on The Late Show with James Corden: "Honestly, it's really like [Swift] started it, and it's time for her to finish it ... It was a full shutdown and then she writes a song about me, and I'm like, 'Okay, cool, cool, cool, that's how you want to deal with it? Karma!"

Exhibit B: The shenanigans that punctured Perry's friendship with mumblecore gloomster Kristen Stewart. According to ELLE UK (via The Independent), the two were great girlfriends until Stewart's split with Robert Pattinson, with whom Perry continued hanging. Perry explained her side thus: "I sent [Stewart] a text message saying: ... 'You know I would never disrespect you ...  I'm just trying to be a friend to him, but it is unfortunate that I do have a set of t*ts.'"

Exhibit C: Rihanna will allegedly never let Perry stand under her umbrella again, since Perry voiced displeasure about RiRi's relationship with Chris Brown. In 2013, a source told US Weekly they "aren't tight anymore because Katy doesn't approve of Rihanna dating Chris Brown." 

All we know for certain: In Katy Perry's world, one can't be afraid to catch feels –particularly the icky kind.