Ben Shapiro Plays Guess The Celebrity

May 9, 2026

AI Summary

5 min read

Ben Shapiro and his guest Savvy play Headbands, a game where each wears a headband displaying a celebrity's image visible only to the opponent. They ask yes/no questions to guess the identity, leading to quick wins, prolonged struggles, and banter over clues like drug use, politics, and personal annoyances.

Quick Sports and Acting Guesses

The game starts efficiently. Ben guesses Tiger Woods after confirming a Black male athlete who has done drugs—Savvy affirms Woods' drug history beyond just alcohol. Savvy then identifies Timothée Chalamet, an under-40 actor Ben likes, after ruling out Oscars and confirming his appeal. These early rounds showcase straightforward categories: sports for Ben, Hollywood for Savvy. Banter notes poor question strategies, like Ben's initial Will Smith or LeBron James guesses despite non-actor and non-drug clues.

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What you'll learn

1 (00:00) **Cook Unity Ad** - Sponsor promo for chef-prepared meal delivery service
2 (01:07) **ZipRecruiter Ad** - Hiring tool with AI matching for passionate candidates
3 (02:08) **Game Intro and Tiger Woods Guess** - Ben wears headband, guesses black athletic drug user as Tiger Woods in few questions
4 (03:58) **Timothée Chalamet Guess** - Savvy identifies young actor quickly after confirming traits
5 (04:44) **Xi Jinping Guess** - Ben struggles with non-American Asian politician resembling Winnie the Pooh
6 (05:33) **Greta Thunberg Guess** - Savvy pins down young European pseudo-politician in news after many questions
7 (07:45) **Jimmy Kimmel Guess** - Ben spots American late-night host trying politics

+ Full timestamped outline available in the app

Show Notes

Ben faces off against producer Savy in a special game of "Hedbanz" to see who’s the ultimate celebrity guesser. From wild guesses to unexpected roasts, things don’t go quite as smoothly as planned…

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