Dumb and Perfect—Conan O’Brien’s Masterclass in Speechwriting

I’m not sure if I’ve ever clearly expressed this, but being a PR flack was never what I envisioned for myself (bombshell, I know).

In my rosier daydreams, I’m usually a standup comedian. Or, at the very least, contributing in some way to the writing or performance of good comedy.

And while I’m fairly certain I would have also hated that particular daily grind—Would  I really be happy trapped in a writer’s room in Los Angeles? Probably not—that doesn’t mean I don’t still get the occasional pang of envy or regret. Every now and then, I’ll hear a joke or watch a performance that makes me think: “You really should have tried to do this.”

Even more rarely, I’ll stumble upon some comedy that goes beyond funny. It feels like actual art—something that matters. Something that’s important.

Conan O’Brien’s recently being awarded the Mark Twain Prize for American Humor—the most prestigious award in comedy—was one of those moments.

For those unaware, the Mark Twain Prize has been presented annually since 1998 by the John F. Kennedy Center for the Performing Arts in Washington, D.C. to a single individual who has “had an impact on American society in ways similar to” Twain.

The ceremony is typically recorded and made available for public viewing in some way, and while I don’t catch it every year, I always enjoy it when I do. Regardless of who’s being honored, the Mark Twain Award ceremony inherently always has a lot of things going for it: a diverse set of incredibly funny, talented people celebrating someone who is also incredibly funny. It’s a serious award—but it’s also comedy, and that kind of tension is always undeniable to me.

Conan’s ceremony was no different. John Mulaney, Bill Burr, Kumail Nanjiani, Sarah Silverman, and several others, all did a fantastic job of honoring Conan in ways that were thoughtful and sincere while also staying true to their own distinct comedic voices. The 90ish minute special is on now streaming on Netflix, and I obviously recommend that you watch it.

But what really stood out to me—what I’ve now watched several times—was Conan’s 15ish minute acceptance speech at the very end. It was masterful. Everything a speech should be in my opinion.

And since this blog is supposed to probably be at least a little bit relevant to the work we do at Resch Strategies, here are three things Conan’s remarks can teach us about how to go about writing and delivering a truly great speech:

Know your room

Who is your audience? And what’s the point?

When you sit down to write remarks, the first step is to consider the occasion and the tone you want to strike. I know that sounds obvious—but it’s more nuanced than just knowing a wedding is different from a funeral.

Conan nailed this. He accepted his award with the perfect blend of grace, humility and humor. From the start, it’s clear he appreciates the weight of the moment—but he’s also knows he’s there because he’s made a hell of a career out of making people laugh, and this stage is ultimately no different than any other. That’s a hard needle to thread, but Conan does it beautifully.

Balance the moment with the message

In the past year, the Kennedy Center’s board was overhauled by President Trump, who was then installed as its chair. Conan received the award from the old board—but accepted it under the new one. Messy.

Rather than address the controversy head-on, Conan did something smarter: he reframed the moment by returning to Twain himself. He quoted Twain. He honored Twain. And in doing so, he reminded the audience what satire is for—without getting partisan or self-righteous.

Great speeches don’t have to be neutral. But they do have to be intentional. The best ones meet the moment without becoming only about the moment. Conan chose to use his stage to talk about Twain—what he believed, what he stood for, and why he still matters today. It was the perfect message. And it was delivered masterfully.

Be true to your voice

I don’t think I can say much here without giving away the joke, but somehow, Conan managed to couch all of that inside a completely inane, stupid, wonderful bit. He lands the plane so beautifully, and a big part of what makes it so perfect is how the ending is so purely Conan. It was great comedy, but it was also a reminder that the best speeches, and the best communicators, know how to move between tones, speak to the moment, and still sound like themselves.

Now go watch it.