Angelina Jolie Was Called a Homewrecker While She Denied the Affair with Married Brad Pitt

Chelsea Handler publicly shared her dislike for Angelina Jolie for years. The comedian even called her a homewrecker and joked about her adopted son, Maddox.

Brad Pitt, Angelina Jolie, and Jennifer Aniston’s love triangle was arguably one of the most headline-grabbing topics of the mid-2000s. Comedian Chelsea Handler knew it and also got involved in it.

Given that Handler and Aniston are good friends, people considered Handler was attacking Jolie to defend Aniston, but she eventually explained she just didn’t like the “Maleficent” actress. Here’s a recap of the Handler-Jolie feud.

Angelina Jolie during an interview with ExtraTV posted on YouTube on October 1, 2019 [left]. Brad Pitt and Jennifer Aniston in Los Angeles, California, on December 5, 2001 [right] | Photo: YouTube/ExtraTV – Getty Images

Pitt and Jolie met while filming “Mr. and Mrs. Smith” in the summer of 2004. Rumors about a possible affair were everywhere, which must have hurt Pitt’s relationship with Aniston. 

In January 2005, the former married couple separated. That March, Aniston filed for divorce and cited irreconcilable differences. Since then, it was almost impossible for tabloids not to mention Jolie or “Mr. and Mrs. Smith” when reporting Pitt and Aniston’s separation. 

Pitt and Jolie were photographed on a beach in Africa with her then-four-year-old son, Maddox, only one month after the divorce process started.

Angelina Jolie on March 25, 2001 at the Shrine Auditorium in Los Angeles | Photo: Getty Images

At that point, their romance was evident, but they kept denying it. Although Jolie and Pitt got along great, and she thought the world of him, Jolie once admitted that nothing past friendship happened. Jolie explained

“To be intimate with a married man, when my own father cheated on my mother, is not something I could forgive. I could not look at myself in the morning if I did that.”

Jolie also claimed to be single and pointed out that the next man she dated would have to be willing to become Maddox’s father. Since it was an important decision to make, she believed she would stay single for a while. In July 2005, Pitt and Jolie officially confirmed their relationship

After that, Aniston’s then-best friend Chelsea Handler — known for speaking her mind for the sake of comedy — started criticizing even the most seemingly harmless things about Jolie, including her adoptions

In a 2007 Comedy Central special, Handler made fun of Jolie by saying that Maddox was probably mad that he got adopted by a famous movie star and “rescued” from his “third-world Cambodia,” only to visit every other third-world country with his mom.

Handler added that Jolie wasn’t a girl’s girl and that she didn’t seem like a sincere woman.

She added that the boy was probably asking Jolie when they were going to relax in Malibu “like [she] promised.” Three years later, Handler attacked Jolie again by dropping the c-bomb on her.

Apart from calling Jolie a See You Next Tuesday, Handler labeled her as a homewrecker. The comedian added that the “Eternals” actress could rescue as many babies from as many countries as she wanted to, but she wouldn’t trust her. Handler said

“Because when I look into a woman’s eyes and she gives interviews, and she goes, ‘Oh, I don’t have a lot of female friends…’ because you’re a [expletive], that’s why.”

Angelina Jolie at The Museum of Radio and Television on September 12, 2005 in New York City | Photo: Getty Images

The “Chelsea Lately” host also criticized Jolie’s parenting skills and told Andy Cohen on a 2013 episode of “Watch What Happens Live” that she seemed like a “demon.” 

According to Handler, she could notice if someone was good or bad by just seeing them walk. Jolie fell into the latter category as she didn’t strike her as a person she could have a close relationship with.

Angelina Jolie and Brad Pitt on January 8, 2007 in West Hollywood, California | Photo: Getty Images

Handler added that Jolie wasn’t a girl’s girl and that she didn’t seem like a sincere woman but one you wanted to avoid. On the other hand, Aniston was “irreverent,” funny, and she sent her hilarious e-mails.  

As expected, not everybody has been on board with Handler’s comments about Jolie. Still, when people have asked if she considered she’s been “unfairly harsh,” the comedian responded she has just been making fun of the actress by saying what everybody else was thinking.

Handler’s opinion on Jolie was not the only thing that changed over the years.


When Pitt and Jolie’s breakup made headlines, Handler shared the potential reasons behind their divorce, including his reported marijuana and alcohol issues. She joked that the actor probably needed to self-medicate because he married a “lunatic.” 

She added that instead of “being stuck” in a house with “85 kids” and speaking different languages, Pitt could have spent all those years he and Jolie were together hanging out at Lake Como with George Clooney and Matt Damon.

After Jolie and Pitt asked for privacy regarding their divorce, Handler said she would no longer talk about them on TV. However, she urged people to follow her on social media as she would keep making fun of her there.

In 2019, after over a decade of criticizing and coming up with jokes at Jolie’s expense, Handler admitted it was time for her to leave the “Wanted” star alone. The comedian said

“I’m upset that I was so upset with Angelina Jolie. I realized she’s probably just trying to do her best too. I mean, obviously I’m not gonna [sic] hang out with her, but I get it now.”

Handler’s opinion on Jolie was not the only thing that changed over the years, as her close friendship with Aniston seemingly ended in 2017. News outlets started talking about it after they were not seen together in public as often. 

It was reported that their friendship ended after Handler talked to others about Aniston and Justin Theroux’s marriage. Another tabloid claimed they just grew apart.

However, Handler has been candid about how hard it’s been for her to maintain friendships because her go-to reaction when someone makes her mad is to sever ties. In 2019, though, the comedian told an Australian talk show that she and Aniston were still friends.

At the moment, it is unclear what led to the demise of their friendship, but since Handler attended Aniston’s 50th birthday party (along with Pitt and Theroux), it’s fair to say they made amends. Way to go!

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