Just Like That but Funny How to Kill a Joke (and Your Boss)

How to kill a joke (and your boss)

Soon after I began writing for Late Night with Conan O’Brien, a veteran writer took me aside. Correctly identifying one of my almost-daily crises of confidence, he explained that I shouldn’t get so hung up on my day-to-day performance because our job was a “volume-driven business.” At the time I found that imparted wisdom depressingly cynical—like being reminded by your platoon leader as you head into battle, “Don’t forget, we’re all sponges designed to soak up bullets. Now have fun out there!” However, a couple years into this, I’ve come to accept that writer’s words as incredibly practical wisdom. On a typical workday, late-night writers produce a ton of material, written almost at the speed of instinct—only some of it will make it through rehearsal, and a fraction of that might survive the hour during which it was broadcast and enjoy an unusually long lifespan well into the next day’s overloaded news cycle. And, while it’s certainly possible to create solid, enduring comedy under those conditions—miraculously, it happens quite often—there’s no doubt you’re at a statistical disadvantage.

For the handful of ways a comedy piece can succeed, there are countless combinations of factors that can sabotage it. Here are just a few:

Fallible Humans

Conan’s writers feature prominently in the show’s sketches. It’s fortunate our show is staffed with a number of writers who are also solid performers, and a couple writers who are outstanding performers. Also, it’s cheaper to cast us. But there’s a third and very compelling reason that only a few outside performers make their way into sketches, and are then cast over and over again, sometimes multiple times in a single show: Comedy is difficult, and highly subjective. What might have worked just fine on one comedy show can come across as broad, or grating, or borderline self-loathingly racist on another. I’ve seen so many promising ideas derailed by performances that were knowingly funny—the worst kind of funny.

Elderly actors are especially hard to cast for this reason. I suspect it’s because, more often than not, they’re summoning their experience with countless directors who have instructed them to act more “crotch- ety” or “enfeebled,” not trusting they would be able to sufficiently communicate their age with subtle indicators like sunken cheeks, liver spots, and milky retinas.

I once wrote a piece for the show in which we delivered the local fire department a housewarming present: a tree filled with cats. The cats were total professionals, but the elderly woman I cast turned in a performance that made Martin Lawrence’s Big Momma character seem comparatively understated, and the sketch was instantly banished to Planet Hamfist. I suppose I could have tried to correct her but I was taught to respect/be terrified of upsetting my elders.

(And don’t even get me started on elderly Asian actors. It should be required by law that an ACLU lawyer be present on the set whenever you’re shooting a comedy scene with an aged Korean woman.)

Tone Deafness

If there were a late-night comedy show completely run by comedy writers, without any interference from a host, producer, or network, that show would probably be called The Darkest and Most Impossibly Horrible Things You Can Imagine, Presented as Comedy. Every sketch would end with a gunshot or an infant’s stroller engulfed in flames, and the show would be canceled halfway through its opening titles. That’s because most comedy writers are so inured by humor that only the most shockingly toxic ideas can achieve the proper velocity to penetrate their indifference.

Here’s a memorable example among many: When Conan O’Brien was wrapping up his 16-year tenure as host of Late Night, it briefly fell upon the writing staff to come up with a fitting way to put a bow on that particular legacy. Something funny, memorable, and appropriate to the sentimental mood surrounding Conan’s departure from a post where he would surely be missed. What emerged from this assignment was something that looked like the discarded notes of a Hollywood pitch meeting from the director of The Human Centipede. Of the dozens of ideas, an overwhelming majority involved Conan being humiliated or killed in some manner—usually violent, often by his own hand. In various combinations, Conan was shot, hanged, beaten, and thrown into an unmarked grave in the desert; hit by a bus; hit by a taxi; or hit by a bus, then a taxi, while riding a young girl’s pink tricycle. In one scenario I proudly pitched, Late Night was merely a fantasy in Conan’s mind, which was severely addled after being kicked in the head by a quarter horse. According to my pitch, as the final show wrapped up, the real Late Night set would dissolve to a tiny Lego version Conan was playing with on the floor of an employees’ break room at a stud farm, where Conan had spent his last 16 years charged with the task of manually masturbating thoroughbred horses. (I think the final stage direction in my sketch was “In the distance, a horse whinnies in ecstasy.”)

Unsurprisingly, Conan chose none of our ideas and instead made an earnest, off-the-cuff closing statement to camera that was completely appropriate to the moment. I remember being genuinely angry and disappointed he didn’t go with my horse masturbator coda.


There are always unforeseeable and unassailable factors at play, conspiring to hobble a perfectly trenchant commentary on Kirstie Alley’s struggle with her weight. (Forklifts struggle with her weight, too! Am I right? I honestly don’t know if I’m right.) In my personal experience, these have included but were not limited to: poor camera coverage; garbled dialogue; unrealistic false beards; subpar puppetry; missed cues; missing graphics; proximity to the tragic death of a beloved celebrity; an obscure or arcane reference (Daniel J. Travanti, cryonics) or a reference entertaining only to other comedy writers (Bruce Vilanch, Robert Wuhl); an armadillo that refused to keep its fez on straight; and the inclusion of Tom Arnold.

Process of Elimination

I know I’m finding fault with a lot of external factors but, truthfully, the majority of my failures as a comedy writer have rested squarely on my own dumb, sloped shoulders. And sometimes distance is required to achieve proper perspective on those failures. During my brief employment at The Tonight Show with Conan O’Brien, and still in my infancy as a comedy writer, I produced a taped segment called “Hip to Trip.” The idea was this: Tripping and falling down had become a cool national trend once President Obama was captured on tape stumbling into a building. I believed this video represented a new benchmark in my career. I worked on it so hard and long there wasn’t even time to rehearse. Instead, it had to be previewed in Conan’s dressing room at the last minute, for a smattering of producers and Conan’s monologue writers. It did not make it into the show. Later, when I asked one of the monologue writers how Conan reacted, he said his disapproval was immediate and unflagging. He didn’t connect with the actor I’d cast in the lead, and found the premise to be a confusing reach.

I couldn’t believe it. I loved the piece. Loved it so much I would talk about it with anyone who would listen. And when we all left that job, quite suddenly, there were only a handful of sketches and videos I bothered to save on a DVD—that unaired piece being among them.

Recently, I was updating my personal website and uploading some of my favorite videos I’ve written and produced over the past couple years. There was no question in my mind: “Hip to Trip” was going to enjoy its rightful place in my portfolio. I found the DVD, ripped the file, and previewed it before uploading it—not for content, but for digital integrity. The “Hip to Trip” I remembered was edgy, silly, and maybe a little too “weird” for the flyover states. It was difficult to reconcile that “Hip to Trip” with the one I was watching now: a sloppy mess executed in a style more suitable for Disney sitcom than a grown-up comedy talk show.

In retrospect, I think what I’d originally enjoyed about the video—and why I might have mistaken it for something successful, when it clearly was not—was the amount of freedom I’d had to create it. I had (needlessly) cast an actor I admired, commissioned a (completely superfluous) song, and even (cost-prohibitively) filmed one of the scenes on Universal Studios’ “Jaws Lake,” holding up takes because the cheap animatronic shark was sometimes visible in the background of my shot. The video never made it to my portfolio, or anywhere else, and I think a valuable lesson was learned from producing it: I probably should have cast one of the writers.


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