In honor of Jon Stewart’s tenure as the host of The Daily Show, which ended last night, artnet News has rounded up the best art-related segments from the comedian’s 16 years behind the news desk.

As you’ll see, the visual and performing arts are not exactly his favorite topics.

Video still from The Daily Show with Jon Stewart.

1. Guernicut
“Famed Picasso slashed—our prices are insane!” Stewart said by way of introduction to an item on the 1999 vandalism of the Pablo Picasso canvas Woman Nude Before Garden in Amsterdam. The incident, Stewart joked, instantly created “two lesser works, Garden, and Woman Nude.”

The vandal’s criminal history, he added, involved connecting the dots on a Roy Lichtenstein.

“Art jokes,” Stewart explained, barely able to keep a straight face.

Video still from The Daily Show with Jon Stewart.

2. Robert De Niro
When the actor stopped by The Daily Show to promote his documentary film about his father, an Abstract Expressionist painter, this past June, Stewart described the movie, Remembering the Artist: Robert De Niro, Sr., as “very moving.”

Stewart went on to praise De Niro Sr.’s artistic integrity and consistency over the course of his career, saying “there’s never that moment where he’s like ‘What if I paint some soup cans? Yeah, maybe I’ll paint some soup cans.'”

Video still from The Daily Show with Jon Stewart.

3. Portrait Accomplished
“Much like any non-torturing war-starting retiree, George W. Bush has returned to public life, with like, 30 pictures he made,” joked Stewart following the opening of Bush’s Dallas portrait exhibition this past spring, noting that the former president “is a somewhat confounding dude.”

Stewart went on to mock the show’s theme, saying, “While your grandpas may have chosen the beach, or birds on his birdfeeder as their subject, George W. Bush has gone with ‘other people I knew who ran countries.'”

He also latched onto art critic Jerry Saltz‘s critique which mentioned the sincerity of Bush’s work. “That’s our man! Our ‘sincere, earnest, almost childlike’ two-term president. You know, I think that might have been his campaign slogan at one time!”

Video still from The Daily Show with Jon Stewart.

4. Paint Misbehavin’
In this early episode (note the dated Austin Powers joke), Stewart devotes an “Other News” segment of the broadcast to the 2000 exhibition “Apocalypse: Beauty and Horror in Contemporary Art” at the Royal Academy in London.

The show title, Stewart explained, was selected after museum officials decided “‘Junk Thrown Together in a Drunken Stupor’ wasn’t cuttin’ it.”

The host singles out the infamous Maurizio Cattelan work La Nona Ora (The Ninth Hour), 1999, and a work involving a claustrophobic maze that seems not to have stood the test of time quite as well that he retitled Fire Hazard.

Stewart also went for a cheap shot against female performance artists, joking about a woman “whose exhibit consists of strapping her nude body to a giant neon penis, a work she calls Attention-Starved Gallery Whore.”

Video still from The Daily Show with Jon Stewart.

5. Statues of Limitations
Though it is in some ways a very different world than it was when Stewart first took the Daily Show reins, this December 1999 episode just goes to show that the more things change, the more things stay the same.

With Greece demanding the return of the Elgin marbles, Stewart weighs in on whether the British Museum improperly cleaned the sculptures, or whether they were already damaged, “perhaps the result of generations of ardent rubbing by the nymphs of Lesbos.”

Video still from The Daily Show with Jon Stewart.

6. Tim Burton
Timed to the December release of this past year’s film Big Eyes, Tim Burton discussed the stranger-than-fiction story of Margaret Keane, whose husband Walter took credit for her paintings. Burton recalled being puzzled by the popularity of Keane’s creepy-eyed children, and thinking as a child that they were “horror movie images.”

“That sort of thing appeals to you, somewhat?” Stewart asked knowingly. “Sort of influence me a bit,” the director admitted.

Stewart also offered his suggestion for an art-themed follow-up: “You know what would be crazy? Imagine a guy, like trying to do that, like paint these pictures of a guy with like, scissors for hands—something like that. I’m just pitching this out, I’m pitching this out, Tim!”

Video still from The Daily Show with Jon Stewart.

7. We May Have Problems But at Least We’re Not Jailing Artists for 3-D Printing Their Vaginas
This past summer, Stewart dedicated a new segment of the show to the arrest of Japanese artist Megumi Igarashi for selling a template for a 3-D printed version of her vagina.

Stewart defended the artist’s work, saying “you gotta have a back up vagina in case the first one crashes. Just common sense.”

Mainly, he found the case against Igarashi confusing: “I don’t get how a country chiefly famous for superior technology, and let’s call it creative sexuality, has seen the perfect combination of those two talents and decided, ‘no that’s too far.'”

Video still from The Daily Show with Jon Stewart.

8. The Thinking Man’s Wrestling
“Art has been called the thinking man’s wrestling” Stewart said to introduce a segment on the record-breaking $104 million May 2004 Sotheby’s sale of Picasso’s Boy with a Pipe. 

The previous record-holder, Vincent Van Gogh’s Portrait of Dr. Gachet, had only fetched $82.5 million, “so that picture must have sucked,” Stewart deadpanned.

Stewart remained unimpressed by Sotheby’s effusive praise for the work, noting that while the buyer was anonymous, the auction house had released a picture of the winner “upon hearing how much he’d spent.”

An image of The Scream appeared on screen, naturally.

Video still from The Daily Show with Jon Stewart.

9. Gustav Klimt
Stewart only had to wait two years to once again mock the outrageously high prices for famous artworks, when Gustav Klimt‘s Portrait of Adele Bloch-Bauer I sold for $135 million in June 2006.

“As fans of the show, who follow this program for many years know, I am something of an art nut,” Stewart insisted. “I love the art. I got about, 50 pictures, you know, paintings,” he added.

Stewart noted that Adele was clearly superior to Boy with a Pipe. “Any idiot can see that!” he said. He then expertly appraised the Klimt’s value, noting that Adele’s bare, translucent shoulders were worth about $20 million each, while “the sultry yearning of the eyes” tacked on an additional $10.875 million to the overall cost.

Video still from The Daily Show with Jon Stewart.

10. The Dong Goodbye
During September 2011’s special election held to replaced disgraced New York politician Anthony Weiner, Stewart leapt on the euphemistic language being used by news broadcasters to describe the inappropriate “self portraits” that led to the congressman’s resignation.

“I mean seriously, these self portraits show none of the monochromatic grandeur of Picasso’s work during his blue balls period,” said Stewart, as a Photoshopped Picasso-esque phallus appeared on screen.

After a similarly hilarious take on Seurat’s iconic A Sunday Afternoon on the Island of La Grande Jatte, Stewart told viewers to be on the lookout for The Daily Show Presents: D*ck Jokes for Art History Majors. (If only.)

BONUS: Moment of Zen – Stuck in a Vagina

While Stewart didn’t touch on this incredibly important news story himself, he couldn’t help ending this June 2014 episode with a clip of Anderson Cooper suggesting that yes, perhaps the US should apologize on behalf of the exchange student that got trapped in a 32-ton marble vagina in Germany.

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