Podcast Summary: “How Not to Write a Caption”

Podcast: The New Yorker Radio Hour
Date: April 3, 2018
Host: David Remnick (plus Emma Allen, New Yorker cartoon editor)
Guests: Willie Staley and Matt Jordan (creators of Shitty New Yorker Cartoon Captions)

Episode Overview

This bonus episode ventures behind the scenes of the iconic New Yorker Caption Contest, spotlighting two persistent, irreverent entrants—Willie Staley and Matt Jordan—whose caption submissions are, by their own admission, unfit for print. The episode is a lively, irreverent discussion about humor, obsession, Internet culture, and the often-misunderstood process by which The New Yorker chooses its caption contest winners.

Key Discussion Points & Insights

1. The Spirit of Shitty Captions

• Remnick introduces Willie and Matt, noting their unusual dedication—submitting nearly every week, never winning, and always skirting the lines of decorum and printability.
• Their intent isn’t to undermine the contest but to amuse themselves:
  “I'm just trying to make myself laugh. … Like, I'm just trying to die laughing.” (Matt Jordan, 04:33)
• Their blog, Shitty New Yorker Cartoon Captions, has gained online notoriety for its raunchy, meta, and often absurdist takes.

2. Collaboration & Origins

• The pair met through mutual friends at a New Year’s Eve dinner party, bonding over oddball humor.
• Captioning became a weekly ritual:
  “Every Monday morning, I flip open the computer, go to contest.newyorker.com, and then I email Matt or Matt emails me.” (Willie Staley, 04:01)

3. How (Not) to Write a New Yorker Caption

• They deliberately break the “rules”—submitting captions that are crude, overly literal, or self-consciously online in style.
• Quotes demonstrate their approach, e.g.:
  • “Girl, I'm gonna fuck tonight.” (Willie Staley, 02:49)
  • “Hey, cool plaid shirts you fuckin hipsters. Where'd you get em, the fuckin bitch store?” (Willie Staley, 01:36)
• The contrast between their style and winning entries is often vast, highlighting the broadness of humor tastes.

4. Caption Contest Mechanics & Community

• Emma Allen (cartoon editor) reveals both the selection process and the cultural obsession surrounding the contest:
  • “Everyone I encounter in the world, like, the first thing that they'll say to me is…‘I haven't won the New Yorker caption contest. I've submitted for 20 years. My captions have always been better…’” (05:37)
• Historic context: More men submit than women—a fact Allen finds tellingly representative of confidence and disappointment patterns.
• Discussion of algorithms now used to whittle submissions, with the final winner chosen from among the most popular picks.
  • Notable insight: The selection algorithm was borrowed from genetic research at the University of Wisconsin.
  • “It's pretty much more democratic than the US election process at this point.” (Emma Allen, 12:30)

5. "Shitty" Examples vs. Winning Captions

• [08:33] Amy Huang’s “cactus” cartoon:
  • Winning caption: “I thought you said it wouldn't need much attention.”
  • Their caption: “Oh, shit. Oh, shit, shit, shit, shit. Fuck.” (Willie Staley, 09:40)
• [14:03] Hospital IV cartoon:
  • Winning caption: “I was just transferred to the fraternity ward.”
  • Their caption: “It's pomplamoose Lacroix. Lol. I'm, like, addicted.” (Willie Staley, 14:49)
• [16:47] Bird-swarming cartoon:
  • Winning caption considered dull by guests.
  • Their caption: "You've got like 35 birds crawling all over you, my dude." (Willie Staley, 17:35)

6. Internet, Meme, and Millennial Humor

• Their captions rely heavily on meme culture, contemporary slang, lowercase, and an ironically dumbed-down style.
  • “We've definitely, like, honed a certain, like, insanely dumb Internet speak style. Just, like, by virtue of just living in that realm, I think you just slowly get dumber.” (Willie Staley, 16:06)
• They see Tumblr as a natural habitat for their work, thriving on the platform’s appetite for meta and anti-humor.

7. Theories on Captions and Winning

• Researchers have analyzed what makes a winning caption: “novelty, length, punctuation and abstractness and imaginability.” (Emma Allen, 18:27)
• Ironically, the duo often scores well on these without winning—due to, perhaps, not meeting standards of printability or being just too odd (or crude).

8. Editor’s Perspective & Anecdotes

• Allen shares her own history with losing the contest, noting that perseverance without reward is almost a rite of passage—even for the cartoon editor.
• An anecdote about her boyfriend winning the contest—but the prize being revoked for nepotism—highlights the quirks and communal feeling around the contest.
  • “Didn't you see the light?” was the shared caption (20:37).

Notable Quotes & Memorable Moments

• On style vs. substance:
  “That's the classic approach for you.” (Emma Allen, 17:46)
  “I'm now noticing how many times we've described literally but slangily, what's happening in the [cartoon].” (Willie Staley, 18:09)
• On submission obsession:
  “People love the contest. They really want to win. They really want to be a part of it.” (Matt Jordan, 19:28)
• On algorithm vulnerability:
  “Yeah, I think it might be, actually. Oh god, this is a disaster. Russia is gonna be, like, on this.” (Emma Allen, 12:41)
• On humor trends:
  “Tumblr loves when you describe exactly what's happening in an image and then end with my dude.” (Emma Allen, 17:58)
• On personal motivation:
  “I don't really think about it as like, trying to…undermine the contest…I'm just trying to die laughing.” (Matt Jordan, 04:33)

Timestamps for Key Segments

• 00:09 – Introduction; background on the caption contest
• 01:27 – NSFW sample captions from Willie & Matt
• 02:03 – Emma Allen joins; reviewing actual contest entries
• 04:16 – Willie & Matt’s origin story as a caption-writing team
• 05:37 – Allen on public obsession and sociology of contest submitters
• 06:33 – Bob Mankoff and the history of caption submissions
• 08:33 – Case study: Cactus cartoon & discussion of editorial selection
• 12:17 – Algorithmic selection process revealed
• 14:03 – LaCroix/IV cartoon discussion; meme culture
• 16:47 – Bird cartoon & the “literal, slangy” approach
• 18:27 – What makes a winning caption: research breakdown
• 20:21 – Allen’s boyfriend’s winning (but disqualified) caption
• 21:12 – Episode wrap-up

Episode Tone & Takeaways

The tone is irreverent, self-aware, and affectionate toward both the tradition and the absurdities of The New Yorker’s caption contest. The guests gleefully skewer elite pretensions with their anti-captions while Allen offers both editorial perspective and a glimpse into the communal (and sometimes competitive) spirit that the contest engenders. It’s a celebration of humor in all its forms, even those too weird or wild—or just too profane—for the printed page.