Conan O'Brien Needs A Friend · October 5, 2026 · 1h 3m

Owen Wilson

Conan O’Brien chats with actor Owen Wilson about his path from military school to his creative partnership with Wes Anderson, the surprising skill of learning how to wear a cowboy hat, bringing Timothy Olyphant on for season two of Stick, and his new film Rolling Loud: The Movie.

This summary was generated from show notes and public descriptions, not from a full transcript review. Details may contain inaccuracies.

Preview

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Military school as an unexpected path to creative partnership

Owen Wilson describes how his experience at military school eventually led to his collaboration with Wes Anderson.

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The art of wearing a cowboy hat

Conan and Owen discuss the practical and stylistic nuances of how to wear a cowboy hat.

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