Theirs is a classic story: a guy meets a guy at a party and they embark on a ten-year journey of virality and pseudo-ironic humor. Matt Jordan and Willy Staley first hit it off on New Year’s Eve of 2009. Upon realizing their shared love of The New Yorker’s cartoon caption contest, they began submitting shitty captions together—and documenting them on Tumblr in the process. A few years later, they moved to Instagram.

The @ShittyNewYorkerCartoonCaptions admins celebrated their ten-year anniversary this past December. I talked with Matt and Willy about the zeitgeist, what they’ve learned, and how they still aren’t verified on Instagram. (Instagram, if you’re reading this, give them a blue check.)

Lithium Magazine: First off, congratulations on ten years of running Shitty New Yorker Cartoon Captions! How does it feel?

Willy Staley: Well, we still haven’t won, so that’s a little frustrating. 

Lithium: So, you haven’t found a way to beat The New Yorker’s algorithm just yet. 

Matt Jordan: (Laughs) I suspect we would have to sacrifice certain aesthetic qualities that we’ve committed to to beat the algorithm. 

Lithium: What is your writing process like? 

Willy: It’s always collaborative, but there’s always one principal writer. Really a Hollywood process. 

Lithium: How long does it take you to write a caption from start to finish?

Matt: It can take all week. Sometimes it’s immediate, sometimes we just nail it in an afternoon. 

Lithium: Did you ever submit earnest captions to the contest? 

Willy: I remember thinking when I first moved to New York that I had a really good idea for the contest, and submitted this caption that of course didn’t make it. 

Lithium: That was your Joker origin story. 

Willy: I was radicalized. I tried once, I gave it my best, and nothing. So I went to war. (Laughs) 

Matt: I’m getting the sense that [New Yorker cartoon and humor editor] Emma Allen’s got a long game of trying to edge out the magazine’s humor portfolio and expand the boundaries. I think over the next few years you’re going to see edgier and edgier comedy, by slow measures, coming out of The New Yorker. 

Lithium: Maybe in ten years, if you’re still running the account, you’ll have a higher chance of winning. 

Matt: What I’m saying is, we’re influencers. 

Willy: I’m the one who’s going to say, I’m not trying to take credit for a change in the tone of The New Yorker’s captions. I want to distance myself from that statement. (Laughs)

Lithium: You guys have created this desperate-to-win-but-can’t-get-it-right character—the imbecile—and the captions you submit are on his behalf. Does the imbecile’s obsession with winning the contest come from your own obsession, or at this point is it just a long-running joke? 

Willy: Maybe I’m different from Matt here. I actually did want to win the contest and thought it was possibly within my reach, but then I found that winning for losing is something you can do online. Some of the cruel desire in my younger self is in there, but Instagram has allowed us to expand the imbecile and bring him to life more. 

Matt: I would love to win the contest. If anybody’s sort of talking down to me or treating me rudely in line at the bank, I’d be like “Wait a second, are you familiar with The New Yorker?” I see a lot of comments online that suggest our followers think we’re performing a deep critique of The New Yorker or its cartoons. I don’t see Shitty New Yorker Cartoon Captions like that at all. What it is to me is a fun writing project with my friend that we get a kick out of. What it’s not is a mean-spirited critique of The New Yorker or its cartoonists… although, maybe it is a critique of the winning captions. 

Willy: I was going to say, we remain critical of the algorithm and its sort of punitive effects on voice and humor. 

Lithium: Do you feel like you’ve cracked the code on how to win the caption contest or just how not to? 

Willy: I think we’ve cracked how to win for losing. You can amass an audience for fucking up repeatedly so long as you play it loose with the copyright law. (Laughs)

Matt: A couple years ago we were asked to do this comedy show where the whole concept was failure. Our bit was sort of like we’ve never succeeded, and we’ll walk you through how we fail. A bunch of people showed up, and one of them was Joe Dator, who is one of my favorite New Yorker cartoonists. He’s such a smart, nice guy. 

Willy: Yeah that was really cool. I think the cartoonists get that we’re on the same team. We’re big fans of theirs, and we do it out of love. 

Matt: It’s really exciting to me when the New Yorker cartoonists like our shit. That’s probably one of the most gratifying things. 

Lithium: What are your inspirations beyond millennial culture? 

Matt: Politics and the disappointing aspects of American and late capitalist culture. Some of my posts are me trying to express, in a roundabout way, something that disgusts me about society. I don’t know if that’s inspiration or trying too hard. (Laughs)

Willy: It’s a lot of Saturday morning cartoons rattling around in my head that offer reference points for a lot of the tropes available in the New Yorker cartoons. Aggressively applying the wrong tone repeatedly to the same set of images—I’ve always found that really amusing. 

Lithium: How important is it to you that your captions actually capture the political or cultural zeitgeist of the time? 

Willy: Very important, insofar as this is a critique of what the contest values and validates—sort of pithy, brief, and somewhat pointless throwaway lines.

Matt: And often timeless.

Willy: Ours are timely in the way that posts on social media have to be: relevant and responsive. In the argot that young New Yorkers speak in. 

Lithium: How has internet culture changed over the ten years you’ve been running the account? 

Matt: Ten years ago, the internet was more of a fringe property, and CNN would write these sort of “haha isn’t it interesting” pieces about the hashtag. In 2010, there was culture and internet culture. In 2020, I think it’s the same. 

Willy: That’s well put, Matt. I cosign that. You can attribute that to me. (Laughs) 

Lithium: Do you want the account to grow into something more or do you like the space it occupies on the internet? 

Willy: We used Cameo to have Riff Raff and Shaggy 2 Dope do caption submissions back in April. We have an idea of starting an OnlyFans—to kind of follow the Substack “premium tier” that’s happening in our own way. It would allow us [to give] paying customers images, which would allow us to do additional content. We really like using Cameo to get celebrities to do their own submissions. 

Matt: It turns out that minor white rappers are extremely good at bad captions. (Laughs)

Lithium: You guys should get Caroline Calloway to do a Cameo if you go the OnlyFans route. 

Matt: Caroline is a fan of the account! We messaged with her a little bit. She’s got bigger fish to fry, though—she’s got the world to take over in some strange way. 

Willy: I just really want her video-caption submission. She’s a spokesperson for the generation. She’s really prolific. What she’s managed to post her way into and out of is pretty unbelievable. You have to respect those numbers and the audacity. 

Matt: And her fearlessness with respect to the ever-present sword of cancellation hanging over her. 

Lithium: What are some online touchstones for you?

Willy: We often run into problems with meme accounts, because they treat our creations as found-object memes, which can be vexing. Though there are meme accounts we do like, like @inzane_johnny. The idea with most internet memes is that the fingerprints are gone and anyone can add their spin to it. But when we’re essentially looked at as a meme account, we’re stripped of our authorship, which can be kind of annoying. 

Matt: I want Instagram to fucking bluecheck us, so it gives us a bit more street cred when we raise a little smoke with these meme accounts who take our shit. But I like @fakeyeezyboosts and @bloatedandalone4evr1993, and @gayvapeshark who passed away last year. In terms of accounts that I see offering broader cultural touchstones, I like @ripannanicolesmith and @teenagestepdad. 

Willy: I personally am a big fan of the podcast Hollywood Handbook. I’m a big fan of the Twitter user @getfiscal, Don Hughes, the legendary Canadian leftist troll, he’s really funny. 

Matt: If you look at our follow list, a lot of it are accounts we actually enjoy, but a majority of it is almost performative—like, accounts somebody who’s chasing clout would follow.     

This interview has been condensed and edited.

Illustration by Seb Westcott