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Top 30 Legendary Jon Stewart Moments

WatchMojo.com | April 23, 2026



From political takedowns to heartfelt moments, Jon Stewart has left an indelible mark on American media. Join us as we count down the best times this comedian and commentator showed his genius! Our countdown includes his advocacy for 9/11 first responders, his return to The Daily Show, crushing Crossfire, and more! Which Jon Stewart moment had you cheering the loudest? Whether it’s his emotional 9/11 response, his fierce interview with Jim Cramer, his Rally to Restore Sanity, or his defense of trans rights, Stewart has consistently used his platform to speak truth to power while making us laugh. Did we forget another entertaining clip from Stewart’s career? Let us know in the comments below!

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#JonStewart #DailyShow #Comedy #PoliticalSatire #LateNight #Colbert #Interviews #Fox #CNN #Trump #911 #Activism

Written by WatchMojo.com

Comments

This post currently has 47 comments.

  1. @MrTumshie

    April 23, 2026 at 1:28 am

    I had somehow managed to forget Glenn Beck existed, thank you so much for the reminder. Being Scottish and living here I had only ever encountered him as a ridiculous figure of fun on the internet. I'm strangely grateful to him for quite a few good belly laughs during what was a difficult time for me personally. But maybe the truly oddest thing about Glenn Beck is that he probably wouldn't be out of place in the current US political media space. Imagine being able somehow to tell yourself from back then that in a decade or so there would be a US president more ludicrous than Beck and George W combined…
    Beck wouldn't be the only one getting ridiculed!

  2. @zacox

    April 23, 2026 at 1:28 am

    I was at the Rally to Restore Sanity! That was such a cool day, the most people I have ever seen in one place. We were packed in the DC Metro like sardines leaving that evening.

    The Crossfire moment was probably the best; I used to watch that show, and CNN in general, a lot when I was in high school, especially after 9/11. But that did it for me. It really opened my eyes and broke the spell of how much American news media is a total sham. It's a shame that all of Stewart's lambasting of the media since then has not had a similar effect.

  3. @bacardy330

    April 23, 2026 at 1:28 am

    Im French Canadian, during the pandemic I started to look at Trump news on youtube and then I watched J. Kimmel since. But when he got canceled, I saw John Stewart for the first time, same tie as Trump and golden background. It was brilliant. I guess I could say the I knew him because of the youtube algorithm.

  4. @sebastianwrites

    April 23, 2026 at 1:28 am

    13:45 mins in, and again Jon Stewart, it is very easy to object to something, but to take responsibility and act like George W Bush did on Iraq, and this is why there are not people being murdered their now in mass slaughters as there had been in the past.

  5. @sebastianwrites

    April 23, 2026 at 1:28 am

    I like Jon, but his take on the Iraq War is stupid, sorry but it is!
    Hussein murdered "100 000s" of people, if we hadn't of gone in, then he'd still be doing that now.
    So to ignorantly say, "This was the biggest foreign policy mistake in the last 100 years" when hypocritically Jon and others would be now complaining of Hussein's horrendous murders if we had not gone in! It's just very easy comfortable middle or upper class people saying they don't like something, but then again 'hypocritically' refuse to do anything about it?

  6. @johnjacobson2015

    April 23, 2026 at 1:28 am

    @WatchMojo One of my favorites is The Charlatan's Web episode about the EPA director Jon Beale who didn't work a single day at the office for 12 years and how far he went to get perks for the job he did not show up at. Best quote from Jon about the segment. "This man is a liar and boring as F***." Not as popular as other moments but its one of the funniest moments with the House Oversight Committee in utter disbelief.

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