Mad Men had a major role in Jon Hamm’s life, both professionally and personally. His performance as Don Draper earned him Golden Globe Awards and Primetime Emmy Awards. During this time, he also met Anna Osceola, who later became his wife. Hamm has spoken fondly about his relationship with his wife. The two connected through their work and share a similar passion for acting and even music.

But apart from being Hamm’s wife, Osceola also has a story of her own and a career that is worth knowing.

Anna Osceola is an actress who moved from Massachusetts to Los Angeles to pursue her career. She recently starred as Maggie Haber in Your Friends & Neighbors (2025). Before that, she appeared in shows like Rizzoli & Isles, NCIS, and Law & Order: True Crime. 

Osceola also had a role in the final season of Mad Men, where she played the role of California coastal retreat receptionist, Clementine. It was during the filming of the 16 Emmy Award-winning series that she met Hamm. The couple later made their red carpet debut at the Academy Awards in 2022 and got married in 2023 at an intimate ceremony in Big Sur, California.

In an interview with The Hollywood Reporter, Hamm shared that he did not think much about marriage since his parents' early divorce. And that also made him nervous when he decided to propose to Osceola. Although he knew that he had found the right person, he was terrified. 

"I don’t know. I just remember feeling, 'This is really scary,' " Hamm told The Hollywood Reporter. "Then going, 'Well, it probably means it’s worthwhile.' And my wedding day was perfect. Everybody I love was there."

Cut to the present, the two are the perfect adorable couple. When asked about kids, Hamm shared that they have not thought about it, but they have not given up on the idea. The two clearly have a lot in common, and even their music preferences.

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Hamm also revealed that both admire Bad Bunny’s music.

During the promotion of Your Friends & Neighbors, Jon Hamm made an appearance on the Happy Sad Confused podcast, where he spoke about his and his wife, Anna Osceola’s shared admiration for Bad Bunny. He even described the artist’s music as the “soundtrack” of their marriage. He added that Osceola had been a fan long before Bad Bunny became a global name.

"Well, before he had established himself on the radio here, and in many ways it has been sort of a soundtrack to our relationship together," Hamm said. "And that's probably the reason [I'm a fan]."

 Speaking to Apple Music, he recalled how she once saw him perform at a dance club in Colombia. The couple was also spotted together at the Super Bowl 2026 to witness his halftime performance, where Osceola wore a jersey featuring Bad Bunny’s name. The artist’s music inspires hope and love, and that also seems to be the connection for Hamm and Osceola. 

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Did you know about Anna Osceola? Let us know in the comments.