Jimmy Kimmel and Staff Surprise Guillermo's Halloween Party

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The late-night host turns up unannounced for his sidekick's annual costume gathering.

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Jimmy Kimmel shows up uninvited to Guillermo's Halloween costume party in a new sponsored segment from Jimmy Kimmel LIVE, turning what starts as Guillermo's own celebration into a surprise appearance by his boss. The bit, sponsored by Smirnoff, finds Kimmel joining in as the show's staff gathers in costume for the occasion.

Guillermo, the longtime on-air sidekick and fixture of Jimmy Kimmel LIVE, has built a recurring on-screen persona over the years that often centers on his reactions to surprises sprung on him during the show's sponsored bits. This segment follows that same format, with Guillermo's party serving as the setup for Kimmel's unexpected arrival.

The segment keeps its focus on the costume party itself, with the Jimmy Kimmel LIVE staff dressed up alongside Guillermo as Kimmel crashes the gathering. The sponsored format places the celebration front and center, giving the bit its comedic momentum as Kimmel inserts himself into an event meant to belong to Guillermo alone.

Guillermo has appeared in other sponsored segments built around his established personality, including a Thomas'-sponsored bit about his dislike of mornings , continuing a pattern of using his on-air persona as the premise for these comedic pieces.

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_Originally reported by [BroadwayWorld](https://www.broadwayworld.com/bwwtv/article/Jimmy-Kimmel-Crashes-Guillermos-Halloween-Costume-Party-With-the-Whole-Staff-20261002)._