Name: Top 10 Most Hilarious Jon Stewart Moments on The Daily Show
Uploaded: 2025-07-18T16:56:56.000Z
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Elmo, you know what we're here to talk about.

Welcome to WatchMojo, and today we're counting down our picks for Jon Stewart's most side-splitting contributions to the political news satire, The Daily Show.

What an incredible display of the awkward tension that happens when your son is dating a biracial girl and you meet her parents for the first time.

After a nine-year hiatus, Jon Stewart triumphantly returned to The Daily Show in 2024 with weekly Monday appearances, and he has not missed a beat.

Offering up an A-grade skewering of Donald Trump and Joe Biden,

Stewart hilariously riffed on the then-presidential candidates' ages.

They are the oldest people ever to run for president, breaking by only four years the record that they set!

Further proof that the hosts still knew how to turn political dysfunction into gut-busting comedy came after the chaotic Donald Trump vs. Kamala Harris ABC debate.

Jon went live with several scorched-earth takes and dumbfounded reactions, all while he expertly dissected the evening's occurrences.

In Springfield, they're eating the dogs, the people that came in.

They're eating the cats. They're eating...

They're eating the pets of the people that live there.

Number 9. Faith Off. Easter vs. Passover.

As a father of mixed-faith children who are exposed to both Christian and Jewish holidays,

I can't help but feel that we Jews are getting our asses kicked out here.

Jon Stewart has long embraced his cultural Judaism with humor and self-awareness, and nowhere was that clearer than in this classic Daily Show segment.

With mock-jealous exasperation, Stewart compared the two springtime religious holidays,

Easter and Passover, and hilariously lamented how Christians were simply better at marketing theirs.

Easter weekend is an observation of Christ's crucifixion and resurrection, so...

Stewart essentially laid out the case that while the story of Exodus is epic, slavery, plagues, escape, somehow it ends in a dinner that feels like homework.

Would you like the treats a magical bunny brought you, or...

With biting wit and cultural affection, he turned religious comparison into comedic gold, pointing out that when it came to branding, Judaism might need a new PR team.

Which egg am I gonna go for? The one filled with chocolate, or the one filled with egg?

Cause that's what slaves ate! Taste it! Oh, wait!

When Vice President Dick Cheney accidentally shot a friend during a hunting trip in 2006, late-night talk show hosts had a field day. John Stewart was no exception.

Making 78-year-old Harry Whittington the first person shot by a sitting veep since Alexander Hamilton. Before diving into the headline-grabbing story, our award-winning host first gave thanks for the comedy Goldmine.

But Stewart didn't just mine the incident's absurdity for laughs, he dug deeper, poking holes in the very premise of the hunting expedition itself.

He also cleverly poked fun at the then-Vice President's response in the aftermath, all before offering parents at home a bit of surprisingly valuable wisdom.

It was peak Stewart. Political scandal turned surreal comedy gold.

If there's one thing John Stewart does better than most, it's exposing political hypocrisy.

Especially when it comes from those in power.

In this highly entertaining 2003 segment, Stewart holds up a mirror to George W. Bush, contrasting the promises he made as a presidential candidate with the very different actions he made while in office.

Through cleverly edited footage, Stewart highlights Bush's many contradictions with a mock debate, complete with himself as moderator.

It's biting, brilliant, and above all, brutally funny.

Of course, this is far from the only time George W. Bush was a target for Stewart.

By 2004, John Stewart had perfected election night satire, and was arguably at the height of his comedic powers.

Along with his equally hysterical correspondence, including Stephen Colbert in all his satirical right-wing glory,

Stewart offered a pitch-perfect skewering of that year's political contest and all the players involved, centering on President George W. Bush and Democratic challenger Senator John Kerry.

In fact, this coverage earned The Daily Show its second Peabody Award, proving Stewart and company were not just following politics, they were rewriting how comedy responded to it.

John Stewart took CNBC and Mad Money host Jim Cramer to task. Hard. You see,

John went to town with a damning and hilarious montage of Cramer giving reckless advice.

And when Jim Cramer himself appeared on the show, Stewart proceeded to tear him apart with surgical precision, while still landing jokes like

And while the interview started off civil enough,

Stewart quickly exposed his hypocrisy with clips from 2006.

These clips were responsible for introducing the phrase into The Daily Show lexicon. Essentially, a code for your career is over.

When John Stewart showed up on CNN's long-running political debate show Crossfire in 2004, he flipped the script. The Emmy-winning funnyman pleaded with the hosts, including a young Tucker Carlson to, quote, ultimately taking them to task. Fast forward some 20 years, and Stewart was once again taking aim at Tucker, this time over his fawning interview with Vladimir Putin. Stewart went on to hilariously mock Carlson's softball questions, strange facial reactions, and giddy endorsement of Russia.

Yep, it was a full-circle takedown that proved Stewart's comedic aim had only sharpened with time.

Few targets received as much of John Stewart's gleeful scorn on The Daily Show as Fox News and its many on-air personalities. And no takedown was quite as, well, musical as this one.

And I believe this country should provide some kind of social safety net for our most vulnerable citizens. Communists. When Stewart called in a full gospel choir to sing the phrase go F yourself, it became hilariously soulful stuff.

He's got a point now. He's got a point now.

Bernie Goldberg, I don't need to satisfy your version of what fair satire is or should be.

I'm not fair. I'm not balanced. He's unstable.

The stunt proved genius, with Stewart turning Fox News' hypocrisy into a full-blown Broadway number.

The joyful delivery, not to mention John's dance moves, contrasted perfectly with the brutal message, making it one of the show's most iconic and cathartic bits.

It wasn't just satire. It was a roast wrapped in choir robes.

When former Alaskan Governor Sarah Palin hit New York in 2011 to meet with reality show star and future president Donald Trump, John Stewart was initially heartened by their choice of cuisine.

However, his joy quickly curdled like bad mozzarella.

First, Trump dragged Palin to a generic pizza joint. Red flag number one.

The place is called Famous Familia Pizza. It is an Albanian chain of pizzerias.

Then came the pizza stacking. Faux pas number two.

But the ultimate insult? Trump, a self-proclaimed true New Yorker, ate his pizza with a fork.

Stewart's brain seemingly short-circuited, launching him into a legendary, and not to mention hilarious, rant for the ages, all while he questioned Trump's New Yorker credentials. Before we continue, be sure to subscribe to our channel and ring the bell to get notified about our latest videos. You have the option to be notified for occasional videos or all of them. If you're on your phone, make sure you go into your settings and switch on notifications.

Few late-night parodies have ever hit harder or funnier than Jon Stewart's epic takedown of Glenn Beck's chalkboard-fueled rants.

When Beck jumped from HLN to Fox News, his profile soared along with his views and theories.

And so, Stewart saw a golden opportunity and delivered an impression that perfectly captured Beck's wild-eyed logic and often outlandish theories.

The high point came in March 2010, when Jon, armed with a chalkboard and an arsenal of random photos, drew absurd connections between progressivism, Nazism, and even Burt from Sesame Street.

The result was a comedic autopsy, and it was absolutely hysterical.

Tell me word on the board, who is doing the lying?

Which Daily Show moment with Jon Stewart cracked you up the most?

Before you eat it, make sure you dip it in salt water, it represents the tears of your ancestors. Oh good, I see you're making more.