Jon Stewart wishes Angelina Jolie had picked him over Brad Pitt in wild moment: "We could have..."
Jon Stewart and Angelina Jolie had worked together just once in the 1998 film 'Playing by Heart', and even after many years, it looks like Jolie left a strong impression on Stewart. The long-running host of 'The Daily Show' just couldn't stop flirting with Jolie when she appeared on the Comedy Central show in December 2014. The moment she arrived, Stewart said, "Ever since I met you about 20 years ago on set, I thought, ‘This person has talent coming out of everywhere.’" Clearly smitten by Jolie, he added, "You meet certain people and you go, ‘This person embodies something different, special.’ I’ve always thought that about you." Stewart who wished Jolie had ended up with him instead of her then-husband Brad Pitt, even joked about a possible nickname for them. "If you’d ended up with me instead of Brad Pitt, our portmanteau – Stewart and Jolie – would have been ‘Stolie,’" he said. "We could have been a vodka brand!"
Jolie appeared on 'The Daily Show' to promote her directorial film, 'Unbroken', which Stewart praised; calling it "epic." The movie, which tells the story of Louis Zamperini, an Olympic athlete and World War II prisoner of war who survived 47 days at sea, was a major project for her. "It took me off-guard," Jolie admitted. "I remember waking up in the middle of the night thinking, ‘I don’t know how to film a shark attack.’" She explained how she approached the challenge. "You convince the studio, you say, ‘You should give me this job, I know exactly what I’m doing. I’m so sure of it.’ And then you get the job and you go, ‘Oh my, I’m not sure that I do.’ So every day was a challenge."
Jolie had previously directed 'In the Land of Blood and Honey' in 2011, which she also wrote. When asked if she enjoyed the "huge responsibility" of directing, Jolie said, "I love directing." She added, "You’re there from the beginning until the end, shepherding every tiny detail." Stewart asked if Jolie’s interest in directing stemmed from working on films where she felt different choices could have been made. In response, Jolie admitted that there were some movies of hers she hadn’t watched because she "couldn’t sit through them." Leaning in with a knowing look, Stewart met her gaze and said, "Do you want to talk to me about them, because I’ve seen them all."
Jolie then returned the compliment, mentioning that she and Pitt watched 'The Daily Show' at home. However, Stewart quickly became more interested in Pitt’s attire while watching. He asked what the former PEOPLE Sexiest Man Alive wore while tuning in. He asked, "Was it just pajama pants and no shirt?" "Sometimes," Jolie replied with a smile. "That feels right," Stewart responded, as per E! Online. In recent news, Jolie attended the Women in Training Inc.'s Annual Mother-Daughter Brunch in Montgomery, Alabama, to support her 20-year-old daughter, Zahara Jolie, on March 4, 2025.
Zahara, a sophomore at Spelman College, delivered the keynote speech addressing period poverty and spoke about the challenges women and girls face due to inadequate access to menstrual products, education, and sanitation facilities. Both Jolie and Zahara dressed elegantly for the event, with Jolie wearing a floor-length silk skirt and Zahara in a knee-length dress. Adeyela Bennett, president of Women in Training, expressed gratitude for Zahara's inspiring speech and Jolie's presence, Page Six reported.