Brier Random
Sarah Funkhouser

Santa Barbara’s Brier Random, an occasional contributor to The Santa Barbara Independent for many years, recently learned that he was selected as a finalist in New Yorker magazine’s popular “Cartoon Caption Contest.”

“Between 6,000 and 10,000 people enter the contest each week, so I’m thrilled to be selected as one of the three finalists this week,” said Random, whose submission is featured in the current issue of the national magazine, which hit the stands and the Internet earlier this week.

He answered a few more of our questions via email last week.

How do you go about coming up with the caption?

The first thing I do is look at the drawing and determine who is speaking. Cartoons can be tricky little things, and often it takes a bit of inspection to figure out where the one-liner will be coming from. You need to look at the mouths in the drawing. The one that’s open, that’s who’s delivering the punch line.

This sound obvious, but sometimes, in a simple line drawing, it’s tricky to figure out. I see a lot of failed Caption Contest submitters who swing and miss because they got wrong who was actually speaking. For this cartoon, it was very obvious that it was the woman, because the man’s mouth was covered by the bag.

Next, I thought the woman looked very kind, and her expression looked like she was trying to compliment him and make light of an awkward first date when her potential suitor had a bag over his head. I thought the only possible kind thing she could say about him was to compliment his eyeholes, along the lines of the cliché that someone has “really kind eyes.” It came to me fairly quickly, and the rest was just getting the wording right.

Do you rally supporters to vote for you or just leave it up to the New Yorker readership at large?

Oh yes, I totally rally my friends and family to vote for me, through email, Facebook, and text messages. You gotta use all the connections you’ve got. Between 6,000 and 10,000 people submit captions for each contest, so an opportunity to be chosen as one of the three finalists only comes around once in a lifetime for most. Plus, I reckon that the other two finalists probably do the same type of self-promotion.

Why did you decide to enter this competition? Is it your first?

I’ve been a reader of The New Yorker since college and a subscriber for a few years, and of course the cartoons are as integral to the magazine as the articles are. The New Yorker has been published since 1925, but the Caption Contest is relatively new, debuting in 1999. When picking up an issue, most people study the cover painting, then immediately flip to the last page of the magazine, where the contest lives.

I vote for a caption almost every week, but I’ve only come up with and submitted something that I thought was worthy about a dozen times. With each submission, I always think, “This is the one that’ll be the winner; how can they not laugh hysterically at this one?” Then, invariably, I’d open the next issue, turn to the last page, and realize that three other hacks had been chosen instead of me (all with captions inferior to mine, of course). That’s when I revisit my own submitted caption and realize that maybe it wasn’t New Yorker material after all.

Why do you think you were selected? Do you have a background that makes you especially gifted for this?

Well, I’ve been somewhat of a writer for most of my adult life, but I never write comedy or “gags.” It’s always been my dream, as with most writers, to be published in The New Yorker. After all, it’s where J.D. Salinger was first published. But I always envisioned that if it ever did happen, it would be for fiction or perhaps poetry. I submitted a poem to them in the ’90s that I thought might have a chance, and I proudly framed my subsequent rejection letter. In those days, they actually sent paper rejection letters, on NYer letterhead. Any writer can be rejected by some anonymous publication, but it takes a special kind of fail to be rejected by the acclaimed New Yorker. Now, of course, it’s all email, and you can’t frame an email.

Did you have any kind of strategy for being chosen as a finalist?

The New Yorker recently published a book called The Cartoon Caption Contest Book, which culled some of the best-of-the-best contests. It included the cartoons, the winning captions, the runner-up captions, a list of a dozen or so of the most oft-used key words for each submitted caption, and little factoids about the contest itself, its history, etc. It’s an interesting book, but I didn’t really take away any information from it that helped me strategize how to pen a winner. I just wrote the best gag I could think of.

One thing I kept in mind was that it should be short, simple, and to the point. That was a must. I think it’s rare that a single-panel cartoon with a caption longer than one sentence can really succeed. The fewer words the better, as it somewhat startles the reader, which kind of jump-starts the laugh.

If you’re selected as the winner, what will it mean to you?

I don’t know what to expect if I win. In the Caption Contest Book, they also included paragraphs written by either the winners or one of the finalists, in which they explained how they came up with the caption, the anxiety and second-guessing it caused, and how it affected their lives. One winner was contacted by a greeting card company and offered a job writing cards. Most were surprised to hear from friends they hadn’t thought about in years, offering congratulations. If I do win, I don’t expect it to profoundly change my life. I’ll probably walk with a little extra spring in my step for a few weeks, though.


The Caption Contest winner will be announced in the magazine and online at on Monday, August 5.


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