Jon Hamm, 55, Opens up About the Worst Movie He Has Seen and Why It Keeps Pulling Him Back

Jon Hamm’s journey from a beloved television icon to a credible film presence is a notorious case study in the entertainment industry. For years, the divide between the small and large screens was a significant hurdle; audiences often struggled to see a performer they welcomed into their living rooms every week as a figure worth a theatrical ticket.

However, Hamm managed this transition with rare sophistication. Rather than chasing traditional leading-man vehicles after defining a generation of prestige drama as Don Draper on Mad Men, he reinvented himself as a versatile character actor.

His strategy has paid off, allowing him to navigate diverse genres while collaborating with industry giants like Clint Eastwood. From playing sharp-witted antagonists in Baby Driver and The Town to engaging in broad comedy, he has avoided the “Draper” archetype to become a favorite of visionary directors.

This success is rooted in his deep reverence for cinema, a trait that surfaced during a recent discussion about his most-watched films. Hamm identified the 1988 classic Die Hard as his top frequent watch, noting that it has become an immovable part of his winter tradition.

His appreciation for the film goes beyond its action-movie blueprint; it plays directly into his annual holiday viewing rituals. While he stands firm in the debate that Die Hard belongs in the Christmas category, he also admitted to a more baffling yearly tradition: revisiting the 2005 dramedy The Family Stone.

Despite the film’s star-studded ensemble, Hamm remains fascinated by how much he dislikes it. “I find that movie fascinating,” he remarked, describing it as an almost inexplicable viewing experience.

“I think it’s an inexplicably weird movie. It’s got a rock-solid, jam-packed, stacked cast, but every time I watch it, I think, ‘this might be the worst movie I’ve ever seen in my life.’”

The film’s plot—centering on a man bringing his polarized fiancée home for a chaotic Christmas—has always been a strange outlier in the holiday genre. However, it gained a new, somber resonance in late 2025 following the death of its lead actress, Diane Keaton.

Keaton portrayed the family’s matriarch, who spends her final holiday struggling with a terminal illness, a storyline that now serves as a poignant tribute to her legendary career. For many families, this coming winter will be the first holiday season since Keaton’s passing, likely turning the film into a genuine emotional touchstone.

Hamm continues to dominate both the streaming and cinematic landscapes. He recently celebrated the premiere of the second season of Your Friends & Neighbors on Apple TV+, where he stars as a disillusioned hedge fund manager who turns to crime.

The series, which debuted its new episodes on April 3, has been a major hit for the platform and also features Amanda Peet and Olivia Munn. Additionally, Hamm voices Mayor Jerry Generazzo in the Disney Pixar film Hoppers.

Whether he is leading a prestige drama or voicing an animated mayor, Hamm’s career trajectory continues to be one of the most unpredictable and successful in modern Hollywood.

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