Bananas, Bosch, and Beyond: The Funniest Works in Art History

In this episode of Art Ed Radio, Tim is joined by Kyle Wood, art teacher and host of the Who ARTed? podcast, for a fun romp through some of art history’s funniest, strangest, and most surprisingly hilarious works. They dig into the surreal nightmare world of Hieronymus Bosch’s Garden of Earthly Delights, the dry conceptual wit of René Magritte, and the internet-breaking audacity of Maurizio Cattelan’s Comedian (aka the duct-taped banana) along with a detour through Renaissance babies with male pattern baldness and Salvador Dalí’s near-death by diving helmet.

Whether you’re an art teacher looking to bring more humor into your classroom or just a fellow appreciator of the wonderfully weird, this episode is a perfect reminder that art history is both stranger and funnier than you might think. This month at The Art of Education, we’re leaning into laughter, and there’s no better place to start than right here.

Timothy Bogatz: Alright, Kyle Wood is with me now. Kyle, welcome back to the show — how are you?

Kyle Wood: I am doing well, thank you so much for having me. Always happy to be here.

Timothy Bogatz: Well, we have a fun one today. We’re going to be talking about some really fun — or funny, or maybe just weird — artworks from throughout art history. I couldn’t think of a better guest to come on, so I’m excited to have you here. Before we dive into art history, can you tell us how things are going for you? How’s the school year? How’s the podcast? Anything else you want to share?

Kyle Wood: Things are going really well. It’s a hectic time — springtime is art show season for everybody, myself included. I’m between art shows right now. I just had my district show the other day, and next week I’m doing a little pop-up gallery at my school. The podcasts have been fantastic. Arts Madness was amazing — tens of thousands of people voting, so thank you to everybody who participated. I hit over 100,000 downloads three months in a row, which is a first for me. That was really validating. And my other podcast, Fun Facts Daily — it’s been going almost a year now — I just love it. I love the fun, the odd, the unexpected. Like, did you know there are two high schools in Illinois with pretzels as their mascot?

Timothy Bogatz: We could only have so many wildcats and eagles — let’s get more pretzels out there! Congrats on the success of the podcast, that’s amazing and well deserved. Arts Madness always gets a lot of attention, so that’s great. Now, the reason I wanted to have you on is that here at the Art of Education this month, we’re doing all sorts of great things about humor in art — art teacher humor, finding the fun, finding the laughs where we can in what is sometimes a difficult job. I came up with a list of artworks that I personally find pretty funny — or at least pretty weird. I’ll get your opinion as we go through, but let’s start with a really old one: the Garden of Earthly Delights by Hieronymus Bosch.

For those unfamiliar, it’s a large triptych — two painted panels on the outside, and when you open it up, three panels on the inside: paradise on the left, a wild scene of excess in the center, and Bosch’s vision of hell on the right. There are some pretty funny, pretty weird things throughout. Kyle, any thoughts before I share a few of my highlights?

Kyle Wood: I was a little surprised to see this one on the “funny artworks” list. It’s odd and unexpected and it’s fascinating, but for me it’s so full of religious symbolism. If I’m remembering Bosch’s biography correctly, he was a real fire-and-brimstone kind of guy — very devout in his beliefs. I believe he witnessed his hometown burn down during his formative years, and some of that seems to come out in the work. So I’m a little bit of a wet blanket here — but yes, it is full of quirky, distorted-looking figures, and the vices and their consequences are all on display.

Timothy Bogatz: Fair enough! On the left side — the paradise panel — there are some really surreal animals that I find kind of fun. And in the center, it’s just people living life to the extreme. Maybe my favorite detail: there’s one figure bent over and somebody else is literally putting flowers into his backside. It’s just so weird — but you’ve got to admit, that’s kind of funny.

Kyle Wood: It is! And there’s also an almost UFO-like quality to some of it. Things floating in the background, spherical structures in the pond — it looks a little bit like Oz, a little bit like Tomorrowland.

Timothy Bogatz: Oh yeah, I can absolutely see that. There’s just so much going on and so much to unpack. Did we even mention the time period?

Kyle Wood: Around 1490 to 1500, right? And that’s what gets me — those were such days when everything was symbolic but not yet abstract in the modern sense. It results in these really weird depictions. You and I were talking before about Renaissance babies and the depictions of the infant Jesus.

Timothy Bogatz: Oh my goodness, yes.

Kyle Wood: The thinking was: we can’t show Jesus as a helpless baby who had to learn and grow. He was born the Messiah. So medieval artists just painted him as a middle-aged baby.

Timothy Bogatz: He was born looking like a 40-year-old man who has already seen some things. One of my favorite internet corners from the last decade was the “Ugly Renaissance Babies” Tumblr — just a collection of the strangest-looking infant Jesuses you can find. He always comes out of the womb looking like he’s lived a full life.

Kyle Wood: And they always give him a receding hairline, just to hammer it home.

Timothy Bogatz: The male pattern baldness really seals it. Anyway — spend some time with the Garden of Earthly Delights. Some genuinely funny stuff going on there.

Another old one worth mentioning — we don’t need to dwell on it — is Netherlandish Proverbs by Pieter Bruegel the Elder. A lot of teachers do the lesson where students take an idiom and illustrate it literally. Bruegel did dozens of them in the same painting: someone literally hitting their head against a brick wall, and so on. It’s a fun one. But let’s fast-forward about 450 years to René Magritte and his famous painting of a pipe with the words “Ceci n’est pas une pipe” — This Is Not a Pipe. Very dry humor, but I love teaching it. Kyle, thoughts?

Kyle Wood: I love it. Magritte was so great with these little works that play with language and perception. Some artists hint at circular reasoning, but I love an artist who makes the subtext into text — literally, in this case. I’m not an intuitive guy; I need things spelled out for me. And as a teacher, I love Magritte for being able to break down these concepts for students: it looks like a pipe, but it’s not literally a pipe — it’s an image of a pipe. It’s drawing our attention to the fault in our perceptions.

Magritte does this across so much of his work. I love Son of Man, too — the self-portrait with the bowler hat and the giant apple covering his face. I didn’t realize for the longest time that it was a self-portrait. A friend asked him to paint one, and he put the apple there “as a matter of conscience,” saying that what we see is always blocking our view of something else.

Timothy Bogatz: Honestly, I’ve always suspected he was just being lazy and didn’t want to paint his face, so he put an apple in front of it.

Kyle Wood: That’s what my kids do! But it’s a thoughtful dodge — and I actually talk to students about that. If you’re going to avoid something, find a way to make it meaningful.

Timothy Bogatz: I also wanted to ask about one of Magritte’s contemporaries — Salvador Dalí. Not to put you on the spot, but do you know if they ever crossed paths? They were working at the same time, both connected to France.

Kyle Wood: I haven’t read anything great about their specific interactions, off the top of my head. But I do love the story of Dalí dressed up in a diving suit — one of those old-fashioned diving helmets — and he almost suffocated. He was trying to signal to people that he couldn’t breathe, and they just thought it was part of the performance. It went on and on, and he came very close to dying.

Timothy Bogatz: And there are just so many other great Dalí stories — the Rolls-Royce filled with cauliflower, the pet ocelot he walked on a leash. But thinking about which of his artworks are objectively funny — I’d go with the Lobster Telephone. I actually got to see it in person at the Dalí Museum in St. Petersburg, Florida. It’s incredible.

Kyle Wood: I’ve seen images of it, but not seen it in person. And now, because we live in the age of AI, the Dalí Museum actually has a lobster phone where you can talk to an AI version of Dalí. They trained it on his interviews, his writing, all of that. There’s a phone number you can call: 722-ASK-DALI, or 722-275-3254.

Timothy Bogatz: I might actually try that. Not a huge fan of all things AI, but I feel like talking to Dalí would be worth it. Okay, I also wanted to mention two more sculptors. First, Claes Oldenburg — I love his giant sculptures of everyday objects. A giant clothespin, a giant comb. There’s an ice cream cone turned upside down on top of a building, which I love. And there’s a giant saw that appears to be cutting the Earth in half.

Kyle Wood: I always love that ice cream cone one.

Timothy Bogatz: It’s great. The other sculptor I wanted to mention is Duane Hanson, who makes life-size, hyper-realistic sculptures of people. I remember seeing one of a custodian pushing a trash can and doing a double-take multiple times — I genuinely kept thinking it was a real person. He has one called The Tourists — a husband and wife dressed head-to-toe in tourist gear — that’s a fantastic and pretty funny piece. Worth looking up.

Kyle Wood: I always feel slightly uncomfortable with Hanson’s work, though. There’s something almost unsettling about looking at a person rendered with such fine detail. It’s amazing — you look at it and think, I know that guy. I’ve sat next to that guy on the bus. There’s something Uncanny Valley about it. On the one hand, I’m incredibly impressed by the skill. On the other, it makes me uneasy.

Timothy Bogatz: That’s fair. Last on my list: Maurizio Cattelan. He’s the author of the infamous Duct Tape Banana — officially titled Comedian — and he also created a fully functional toilet made of solid gold. Do you have a favorite from him?

Kyle Wood: The more I’ve seen of his work, the more impressed I’ve been. I love the banana. But I also love one of his earlier breakthrough pieces — Strategies — where he did a mock-up of his own work on the cover of an art magazine, in the style of the magazine itself, just to gin up publicity. I love a prank without malice. The banana is another perfect example: it’s just fun. It creates controversy without doing anything harmful. And the more I think about Comedian, the more I enjoy it as a piece.

Timothy Bogatz: Great call. If you want a real deep dive into his work, Kyle did a fantastic episode on his Who ARTed podcast that covers a lot of it — we’ll link that in the show notes. Kyle, is there anybody I missed that you want to add?

Kyle Wood: About five minutes before we started recording, I thought of one: Nat Tate.

Timothy Bogatz: I’m not familiar with Nat Tate.

Kyle Wood: That’s because Nat Tate is a fictional artist. He never existed. The story goes that David Bowie was hosting a dinner party on April 1st with authors, critics, and tastemakers, and he decided it would be fun to present Nat Tate — the subject of an upcoming fictional book — as if he were a real person. He got friends to play along; a Picasso biographer would talk about how Nat Tate had been in the same circles, but that he had tragically destroyed nearly 99% of his own work before throwing himself off a bridge. There was actually a published book — a fictional biography called Nat Tate: An American Artist. For about a week, a number of people believed he was real.

Timothy Bogatz: That is incredible.

Kyle Wood: But here’s the best part: there are a few surviving “works” by this fictional artist. In 2011, one of them — Bridge No. 114 — went up for auction and sold for over $11,000. Real people paid real money for a real artwork by a made-up artist.

Timothy Bogatz: Who actually painted it? Do you know?

Kyle Wood: I don’t know for certain, but presumably someone at the publishing house — maybe a graphic designer — made some pieces to illustrate the fictional biography. And now one of them has sold at auction for five figures.

Timothy Bogatz: I need to look that up. That is a great story and a great laugh. Well, Kyle, thanks so much for coming on and chatting about all of these fun, funny, and just plain weird artworks. I always love talking art history with you.

Kyle Wood: Thank you very much. Anytime you want to get weird with art history, I’m your guy for the odd and unexpected.

Timothy Bogatz: I can think of worse reputations to have. Thanks, Kyle.

Kyle Wood: Thank you.