Celebs Who Started Out Friends And Ended Up Enemies

When we think about Hollywood stars who are inseparable, we tend to think about the romantic relationships that have stood the test of time. Take, for example, the marriage of Tom Hanks and Rita Wilson, or the power duo that is Kurt Russell and Goldie Hawn. These relationships should be celebrated, but we tend to forget to celebrate the loving relationships between two celebrity best friends. 

Surely, there are no two friends in Hollywood who come close to having the friendship that Cameron Diaz and Drew Barrymore share. The actors were best buds way before starring in "Charlie's Angels," with Barrymore once sharing to ET, "We're like more than best friends, she's my sister." 

So it goes without saying that it truly is more painful to hear the news that two celebrity best friends have parted ways than to hear that two stars who were once romantically involved have broken up. Friendships have become just as hard to maintain as romantic relationships in Hollywood, and it is sad when two former BFFs are now considered frenemies. Unfortunately, not every friendship can be like Diaz's and Barrymore's. 

These former iconic duos are known more for their nasty feuds than their once loving and inseparable friendships.

The feud between Taylor Swift and Katy Perry will go down in pop history, and while it lasted for quite a few years, it appears as though the women have made amends.

According to the BBC, their feud wasn't necessarily because they both dated John Mayer, but because Perry had allegedly stolen Swift's backup dancers during Swift's Red Tour. For her Rolling Stone cover story, Swift admitted that her then-new song "Bad Blood" was about a certain female artist. "For years, I was never sure if we were friends or not. She would come up to me at award shows and say something and walk away, and I would think, 'Are we friends, or did she just give me the harshest insult of my life?'" Swift said, adding, "She basically tried to sabotage an entire arena tour."

Perry fired back after Swift's Rolling Stone interview with a cryptic tweet: "Watch out for the Regina George in sheep's clothing..." When asked by Billboard if the tweet was about Swift, Perry replied, "If somebody is trying to defame my character, you're going to hear about it." In 2017, the "Dark Horse" songstress appeared in James Corden's Carpool Karaoke segment and discussed her feud with Swift, where she said, "She started it, and it's time for her to finish it ... I'm ready for that B.S. to be done." Time reported that Perry was over the feud, and in 2018, she sent Swift an actual olive branch along with a note that Swift later shared on her Instagram. 

At the start of their careers, Gwyneth Paltrow and Winona Ryder were glued at the hip. The Daily Mail reported that the women were living together in the same apartment, and they ended up dating Hollywood's best pals, Ben Affleck for Paltrow and Matt Damon for Ryder.

However, their friendship crumbled in the late '90s when Paltrow allegedly discovered Ryder's script for "Shakespeare in Love" and auditioned for the role of Viola de Lesseps, a part which was believed to have been given to Ryder first. Paltrow got the role and even won the Oscar for best actress at the 71st Academy Awards for her performance. While Paltrow was celebrating her momentous win, in 2001, Ryder was convicted of shoplifting at a Saks Fifth Avenue in Beverly Hills, which almost ruined her career. 

When Paltrow launched her now-famous website Goop, one of her earlier articles, titled "Evil Tongue and Living in Negativity" addressed a former friend turned "frenemy" that several fans have speculated is Ryder. The actor wrote, "Back in the day, I had a 'frenemy' who, as it turned out, was pretty hellbent on taking me down." Paltrow went on to describe her former friend as "venomous and dangerous" and added, "But one day I heard that something unfortunate and humiliating had happened to this person. And my reaction was deep relief and ... happiness ... So, why does it feel so good to hear something bad about someone you don't like?" As of this writing, it doesn't appear that the two actors have made amends. 

Scientology played a massive role in the feud between actors Leah Remini and Kirstie Alley. The "King of Queens" star left the Church of Scientology in 2013 and has since publicly slammed the faith, even creating a docuseries on A&E in attempts to expose just how controversial the church is. Remini's attempts at revealing information about the church reportedly created tension between her and Alley, who has been a member since 1979.

When Remini sat down with Ellen DeGeneres and shared that she lost friends for leaving the church, it didn't sit well with Alley, who told Howard Stern on his Sirius XM radio show, "You're not shunned. You're not chased. All that stuff's bulls**t," adding, "when you decide to blanket statement [sic] that Scientology is evil, you are my enemy" (via E!). 

Remini would also speak with Stern about Alley's comments, explaining that she understood Alley in light of Scientology's policies. Remini added that she also was fine with Alley blocking her on social media because Alley is "supposed to disconnect from anybody who's antagonistic to what you're doing in your life." According to the Scientology website, a Scientologist who is in training must "disconnect" with a person "who is suppressive or who is antagonistic to" the faith, and may have to cease communications.

Before the infamous Jordyn Woods scandal that would eventually end her close friendship with Kylie Jenner, the two stars had never left each other's side as they celebrated birthdays together and had several twinning moments. Jenner stated on "Keeping Up With the Kardashians" that Woods was lived in her home at one point (via Us Weekly).

Jenner and Woods were so close that the reality star collaborated with her former BFF on a 2018 Kylie Cosmetics line comprised of eyeshadow, highlighter, lip gloss, and lipstick. Woods, who was close to all the Kardashian and Jenner family members, also attended Kim Kardashian's 2014 wedding to Kanye West in Italy and modeled for Khloé Kardashian's clothing line, Good American.

However, in 2019, news broke that Tristan Thompson, the father of Khloé Kardashian's daughter True, was seen "making out" with Woods. Thompson admitted that he had cheated on Khloé (per an Us Weekly source), and Woods appeared on "Red Table Talk" to say that she "did as much apologizing as [she] could" to Khloé. The damage was done, and it appeared that neither Jenner nor the rest of the family have tried to mend their friendship with Woods since the incident. In 2021, during the "Keeping Up With the Kardashians" reunion, Khloé did open up about reconciliation, stating (via E!), "If I can allow Tristan back into my life, I need to allow the same forgiveness and acceptance of other people." 

After her falling out with Kim Kardashian, Larsa Pippen, best known for her former marriage to NBA star Scottie Pippen, had plenty of tea to spill about her former friend and the Kardashian-Jenner family. According to Elite Daily, Pippen was very close to the famous family, but something happened which had Kris Jenner and Kim, Khloé, and Kourtney Kardashian unfollowing Pippen on Instagram during summer 2020. 

In November of that same year, Larsa Pippen appeared on the Hollywood Raw podcast and admitted that Kanye West, Kim's ex-husband, was the one to blame for Kim and Larsa's falling out. "[Kanye] has literally brainwashed the whole family into thinking I don't know what ... He talks so much about me being this and that and this and that." Pippen also shared that rapper Travis Scott, who is the father of Kylie Jenner's daughter Stormi, called Jenner claiming that Pippen was hitting on him. That wasn't all. The reality star admitted that she dated Tristan Thompson, the father of Khloé Kardashian's daughter, True. "I kind of was seeing Tristan before Khloé," she revealed, adding, "Then a week later, maybe 10 days later, he started seeing Khloé."

While the Kardashian/Jenner clan have never publicly commented on Pippen's telling remarks, a source told E! that the famous family believed Pippen was "toxic energy" and shared that the reality star was just trying to stay "relevant." 

Ben Affleck's relationship with his acting buddy Matt Damon is one of the strongest friendships in Hollywood. However, Affleck has also been close to many other stars, including director Kevin Smith, who was responsible for launching Affleck's career. Affleck starred in Smith's 1995 comedy "Mallrats" and would go on to act in more of the director's films, including "Chasing Amy," "Dogma," and "Jay and Silent Bob Strike Back." 

However, Smith revealed that their budding friendship was over once Affleck began dating and later marrying actor Jennifer Garner. During a tour stop for a film, Smith shared (via the New York Daily News), "Jennifer does not share the same sense of humor as me — she did not like my jokes. I was picking on Ben Affleck and making fun of him because I've known him for a really long time — I was talking smack, and Jennifer goes, 'You know, if you keep saying stuff about him, I'm going to kick your a**.' And she could; I've seen 'Alias.'"

When Yahoo Entertainment asked Smith about Ben Affleck in 2014, the director remarked, "I have not been [close with him] in decades. That's old Ben. He's got a wife that don't care for me at all." According to People, the two stars reconnected in 2019, after Affleck agreed to star in Smith's "Jay and Silent Bob Reboot." The director shared an Instagram photo with the actor and captioned it, "Not only did we score an amazing scene for the flick, but I also got my friend back."

Actors Seth Rogan and James Franco had a friendship that spanned decades, starting with their roles on the sitcom "Freaks and Geeks," per Bustle. The men would go on to star in several films together, including "Pineapple Express," "Knocked Up," and "The Interview." 

Unfortunately, their long-lived bromance was cut short when Franco was accused of sexual misconduct toward five women in 2018, per the Los Angeles Times. A lawsuit was filed against the actor in 2019, but a settlement was reached in 2021, per The Hollywood Reporter. Franco has maintained his innocence in the matter, telling Stephen Colbert on his show that the allegations were "not accurate," but it appeared to be too much for Rogan, who cut ties with his former buddy. 

In an interview with The Times, Rogan was asked if he had worked with Franco since the allegations arose and shared, "The truth is that I have not, and I do not plan to right now." When he was asked about the sexual misconduct allegations, Rogan said, "What I can say is that I despise abuse and harassment, and I would never cover or conceal the actions of someone doing it, or knowingly put someone in a situation where they were around someone like that." Rogan could not define his relationship with Franco and agreed that it was "painful," however, "not as painful and difficult as it is for a lot of people involved."

If you or anyone you know has been a victim of sexual assault, help is available. Visit the Rape, Abuse & Incest National Network website or contact RAINN's National Helpline at 1-800-656-HOPE (4673).