Though Handler is making headlines right now for that divorce dig, it's far from the first time she's insulted Jolie. In fact, she seems to have made it her mission to jab at Jolie every opportunity she gets.
Handler brought up Jolie all the way back in 2008 on a Comedy Central special, poking fun at her for adopting son Maddox.
"He probably thought he was scoring the biggest deal of his lifetime, getting adopted by this famous movie star who was going to rescue him from his third-world Cambodia," Handler joked, "only to find out she was going to take him to every other third-world country in the world. He’s probably like, 'When are we going to get to Malibu?'"
Right before welcoming Aniston on the Chelsea Lately show in August 2010, Handler decided to challenge Jolie's reputation as a cool mom.
"What a fun mom! You are so fun, kitty cat. You go, girl!” Handler said of Jolie's story that she dressed up in a NATO uniform to punk son Maddox. “You’re evil and everyone knows it. Thank you for being here. We’re going to be right back with Jennifer Aniston."
During a New Jersey stand-up appearance in 2011, Handler laid into Jolie in perhaps the harshest rant in her history of insulting the actress.
According to Huffington Post, Handler called Jolie a "home-wrecker," among other unsavory phrases.
"She can rescue as many babies from as many countries as she wants to," Handler said. "I don’t fucking believe you... She gives interviews: 'I don’t have a lot of female friends.' 'Cause you’re a fucking c***... you’re a fucking bitch."
In 2013, Handler insisted that her dislike of Jolie had nothing to do with bestie Aniston during an interview on Watch What Happens Live. Rather, she said Jolie just has a bad vibe about her.
"She seems like a demon. It has nothing to do with Jennifer," Handler said. "As a woman, I know when you see somebody walking across the room that’s a bad girl. I just don’t like Angelina Jolie. I don’t think she’s a girl’s girl. I like girl’s girls!"
Handler's 2014 Oscar tweets raised eyebrows when she joked about Jolie's desire to adopt some of the diverse talent at the award show.
Handler didn't waste any time in the wake of the Pitt/Jolie divorce news to hurl some more words in Jolie's direction just this week.
"I wonder why [Pitt] would need to self-medicate,” Handler said of rumors that Pitt has a substance abuse problem. "Maybe because he could have been spending the last 12 years at Lake Como hanging out with George Clooney and Matt Damon instead of being stuck in a house with 85 kids speaking 15 different languages. Oh yeah, because he married a fucking lunatic, that’s why."
Personally, I think it's time for Handler to move on. Enough is enough. It's water under the bridge at this point. If Jennifer Aniston can move on, be happy and live her life separate from Jolie and Pitt, then so should you, Chelsea Handler.
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