REALITY TV
TV
MOVIES
MUSIC
CELEBRITY
About Us Contact Us Privacy Policy Terms of Use Accuracy & Fairness Corrections & Clarifications Ethics Code Your Ad Choices
© MEAWW All rights reserved
MEAWW.COM / ENTERTAINMENT / TV

Angelina Jolie once called out Jay Leno over his disturbing joke involving her and her brother

Angelina Jolie didn’t just let Jay Leno’s jokes slide—she brought receipts and made him read them on air.
PUBLISHED MAR 23, 2025
(L-R) Angelina Jolie speaks at a press conference on September 26, 2007, in NYC; (R) Jay Leno at Hudson River Park's Pier 62 on October 11, 2018 in NYC (Cover Image Source: Getty Images | Photo by Chris Hondros; (R) Jim Spellman/WireImage)
(L-R) Angelina Jolie speaks at a press conference on September 26, 2007, in NYC; (R) Jay Leno at Hudson River Park's Pier 62 on October 11, 2018 in NYC (Cover Image Source: Getty Images | Photo by Chris Hondros; (R) Jim Spellman/WireImage)

Angelina Jolie has never been one to shy away from addressing the controversy, and during a 2001 appearance on 'The Tonight Show with Jay Leno', she proved just that. The then 26-year-old actress confronted Leno about jokes he had made regarding her and her brother, James Haven. The interview started lightheartedly, with Leno commenting on Jolie’s famous Billy Bob tattoo, a tribute to her then-husband 'Billy Bob Thornton'. “I have a Billy Bob tattooed on my arm as well,” he quipped. But the mood quickly shifted when Leno brought up rumors that Jolie and Thornton were upset with him for his past jokes about them. Addressing the issue head-on, Jolie didn’t hold back.



 

“I checked out the jokes after hearing that they were awful,” she said. “However, after checking them, I felt they were too stupid to be angry about.” But then, her tone grew more serious as she continued, “I've been waiting for this. Anybody here knows that when somebody says stuff about your family, it's just not OK. And my mom’s just not been OK about the stuff about me and my brother...” Jolie then handed Leno a piece of paper, telling him to read the jokes he had made. “I highlighted it,” she said. “And there are those that made my mom sick.” Leno, caught off guard, reluctantly read aloud: “One of the main characters of the movie 'Gladiator' wants to sleep with his sister.” He quickly admitted, “That’s bad.” But it only got worse. The next joke on the list? “Billy Bob said that Angelina Jolie was attracted to him but she said, ‘He is like a brother to her.’” 



 

Trying to downplay the moment, Leno asked, “They are not terrible. Are they terrible?” Jolie’s response was cutting: “They’re not terrible. I actually didn’t highlight the ones that were so terrible. I didn’t want my mom to hear them again.” When Leno tried to justify himself by claiming that he wasn’t the only one making jokes about the Oscar kiss between Jolie and her brother, she shot back with a sharp retort: “It’s good of you to jump in with everybody else.” Furthermore, Jolie's brother Haven later clarified the infamous Oscars moment. Per AOL, he stated, “I did not give Angie a French kiss. It was something simple and lovely... I congratulated her on the Oscar win and gave her a quick kiss on the lips. It was snapped and became a big thing.”



 

This wasn’t the only time Leno was called out for his inappropriate humor. Per MediaITE, John Oliver slammed Leno for his hypocrisy when he called out modern comedians for lacking civility, despite his history of offensive jokes. To highlight Leno’s past behavior, Oliver aired a clip of a 'Tonight Show' segment where Leno presented a fake children's book titled 'The Sl-t in the Hat', a crass play on 'Dr. Seuss' The Cat in the Hat,' that mocked Monika Lewinsky, a former intern, at the height of the Bill Clinton scandal. Sarcastically addressing Leno’s so-called plea for civility, Oliver snapped, “If that’s what he means by civility, may I offer my new book, ‘Oh, the Places You Can Go F**k Yourself, Jay Leno.’ Look how civil I'm being. Look how civil this is.”

POPULAR ON MEAWW
MORE ON MEAWW