Updated: August 4, 2015 2:58 PM ET | Originally published: February 10, 2015 8:01 PM EST

There are many notable moments from Jon Stewart’s 16 year reign at the helm of The Daily Show, following his evolution from a comedian to a genuine voice in critiquing media and politics. With Stewart’s last show set for Thursday, here are his top five moments from a long run—including one that took place off The Daily Show set.

The 9/11 Monologue

Stewart vs. Jim Cramer

Stewart shoots down Crossfire

Stewart schools Glenn Beck

Indecision 2000

Read next: 7 Potential Replacements for Jon Stewart on The Daily Show

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Write to Tessa Berenson at tessa.berenson@time.com.

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