You might be wondering how Jon Hamm and Anna Osceola met in the first place. It turns out they first ran into each other on the set of “Mad Men.” While Hamm, of course, played the role of the acclaimed show’s protagonist, Don Draper, Osceola picked up the role of Clementine in the series. Her character was a receptionist at a retreat. For her part, Osceola has been working in the entertainment industry since 2007. Her first role was in the TV movie “Not Another High School Show,” but Osceola has also made appearances in “Rizzoli & Isles,” “Law & Order: True Crime,” and more.
Hamm and Osceola seemingly don’t mind intertwining their careers with their relationship, because they both also took on roles in “Confess, Fletch.” The movie is the third film in the series, which began with “Fletch” in 1989. Hamm portrayed journalist Irwin M. Fletcher in the 2022 flick, while Osceola took on the role of Larry. This seemed to be quite the passion project for Hamm, as he reportedly gave up much of his earnings to make the movie possible.
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During an interview with Uproxx, director Greg Mottola revealed that it was difficult to find partners for the movie, so he and Hamm pitched in themselves before eventually getting some support from Miramax. “So, basically, what we did is Jon gave back 60 percent of his salary to the budget,” he said in part. With this in mind, Osceola’s involvement might have been extra special to Hamm.
