How to Roast Your Friend Just Enough That They’ll Want to Remain Your Friend

Tue, 16/04/2024 - 23:00
Tue, 16/04/2024 - 23:00

In this column, professional speechwriter Chandler Dean provides partly satirical, partly genuine “How To” advice focused on a hyper-specific subcategory of speeches—from graduation speeches to wedding toasts to eulogies, and all the rhetorical occasions in between.

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Tick-tock: the bachelor or bachelorette or bachelorx party is approaching, and your buddy has insisted that they want you to “totally roast them.” Unfortunately, there is no time to question what ignominious circumstances led them to this masochistic desire. There is only time to write jokes.

I’ve written roasts for celebrities and politicians at fundraisers and closed-door events; I’ve roasted coworkers at their farewell parties; I’ve made fun of friends when they made a typo in the group chat and then I’ve changed the name of the group chat to have the typo in it.

So take it from me: you can both get laughs and protect your friendships (and professional contacts, and geopolitical relationships). Here’s how.

Don’t overthink it: you can always just tell a story.

Literally, any time that anyone asks you to talk in front of a microphone—whether it’s a roast or a toast or standup or a reading or truly any occasion—no one will get mad at you if you tell a good, relevant story and then briefly explain why you told that story.

In the case of a roast, think of a quality that you might razz your buddy about. Ideally, it should be something that they themselves would openly admit is true. And then tell a story about them that demonstrates that quality. Are they habitually late? Are they obsessed with some arcane subject? Are they the sort of loser nerd who would use the word “arcane” casually?

Whatever their deal is, think of the last time they were dealing it up, and share that story—with bonus points if nobody else in the room has heard it before. Because as the great storytelling comedian Mike Birbiglia has said, about any form of joke-telling: “If you’re not telling secrets, who cares?”

If you’ve never done capital-C Comedy before, I promise that this is the easiest way to successfully complete the assignment. But if you really want to try your hand at an old-school roast with set-’em-up knock-’em-down jokes, you can proceed accordingly:

Double-check how much they really want to get roasted.

This is a good stage in the process to remember that you are not Anthony Jeselnik. (Unless it so happens that you are Anthony Jeselnik, in which case I am sorry that you are stuck reading this column instead of doing cool Anthony Jeselnik stuff.)

You cannot, will not, and should not pull off jokes about the edgiest or darkest subjects you can think of. These things are always more fun when everyone involved is on the same page, operating at the same level of tact (or lack thereof). Mutually assured dysfunction.

So talk to the roastee. Talk to any fellow roasters. Figure out the vibe. And if you realize on the night that some of your jokes might go too far, it’s never too late to cut ’em on the fly.

Once, I was writing for a tribute—a tribute, not a roast—to a legendary comedian. Most of the comics and actors who participated got the idea: there was room for some lighthearted jabs, but ultimately the tone of the night was meant to be sincere.

There was a journalist on the lineup who just didn’t get it. With every draft we sent them, they kept asking for jokes that were sharper, harsher, meaner—true roast fodder. Despite our protestations, we tried to take their notes without veering the remarks too far into disaster.

By the time they got on the stage, they had clearly sought outside help from other writers who had written some incredibly brutal jokes about the honoree and all the other speakers. Were the jokes funny? It did not matter. The tone was completely off and the journalist bombed—fully violating the comedic Geneva Conventions.

All to say:

There is always a line. Walk up to it; dance upon it; don’t cross it.

The Gridiron Club—where leading politicians, including every president since Grover Cleveland, have told jokes to a crowd of journalists for over a century—has a motto: “singe, don’t burn.”

In other words, it’s fine to make jokes that might sting a bit in the moment, but no laugh is worth causing permanent damage. So err on the side of the forgivable. And if somehow your friend is disappointed that you didn’t go hard enough, you can always privately share the jokes from the cutting room floor.

On that note:

Write more than you need, and trim it down by running your set by people you trust.

For every good joke that a professional comedy writer writes, they’ve written approximately 379 jokes that do not work. Your ratio will be worse.

So don’t be afraid to start with a stream-of-consciousness, self-judgment-free brainstorming process in which you write down every idea, half-idea, and mere notion that pops into your head when you think about this friend and this moment. From there it will be much easier—but still hard—to mold that into a series of usable jokes.

Writing a stand-up set is like delicately chiseling an elaborate sculpture from an enormous ice block, except that before you even get to chisel you have to provide your own ice block. (Not to mention that you have to be self-important enough to think this is a fair comparison.)

If you’re not sure where to start:

Remember the universally acknowledged foundation of any good comedy: research!

In leading the humor team at the speechwriting firm West Wing Writers, every so often we get tasked with scripting a full event script for a roast—writing remarks for all the speakers, including the roastee of the evening.

This is always incredibly fun, but it’s also an interesting challenge, because every speaker is expected to make jokes about every other speaker. That means if there are about a dozen participants, we’ve got to come up with at least a dozen different angles for jokes about each person; you don’t want everyone to do a chunk about, say, Cory Booker’s veganism. (And if Cory Booker is reading this, “chunk” can mean a series of jokes, or it can be used as a verb—as in “I chunked that leftover pizza because it was vegan.”)

So, for each and every person on the dais, we put together a “fast facts” document that includes every piece of publicly available information we could find that could conceivably be used as part of a setup for a joke. There’s no reason you couldn’t engage in this exercise for someone you know personally; start by writing down everything you know about them, especially the weird stuff, and you’re well on your way.

Now, if you don’t know as much about them as you’d like:

Talk to the people closest to your roastee, as they will be most ready to betray them.

My buddy Jonathan van Halem—a fellow Brooklyn comedian—was once hired by a fan to roast a friend of theirs who was being punished for getting last place in his fantasy football league. (Who said that men are facing a loneliness epidemic?)

Of course, Jonathan did not know anything about this person, so he asked his client to gather relevant dirt on the roastee that he could use as fodder for jokes. This friend, with the help of the rest of the league, did not hesitate to oblige him.

The list ultimately included entries like “captain of the chess team in high school,” “tiny hands,” “has not been to the gym in ten years,” “gambling addiction,” and “in danger of coming in last place again this year in fantasy football.”

This is a list of qualities gathered by this man’s best friends in the whole world. But that makes sense: nobody knows our flaws better than the people closest to us. And those are the same people who can get away with good-naturedly pointing them out. Or paying Jonathan to do it.

The key word there, though—or, I guess, the key compound adverb—is “good-naturedly.” So:

Make fun of their choices and behaviors—things they can control.

Look, I’m not going to pretend that roasts have historically been a place where decency and good taste have reigned supreme. There’s no doubt that the genre has a long history of people joking, often tastelessly, about race and gender and sexuality and physical appearance. And some people operate under the philosophy that, particularly in this kind of setting, nothing is off-limits and anyone can joke about anything.

Personally, though, I just think it’s more challenging, more rewarding, and ultimately funnier to dig a little deeper, go beyond the hacky obvious ideas, and speak to the qualities that are truly unique to that individual.

Unless you’re talking about Chris Christie, in which case you’ll be speaking to the quantities that are truly unique to that individual.

Sorry, sorry. Let’s move on. (Unlike the commuters on the George Washington Bridge.)

You still get credit for self-deprecation even if you pull someone else into it.

These are what you might call “ugly guys like us” jokes. Which is to say that you can sometimes get away with calling someone ugly if you jovially throw your arm over their shoulder and say it’s a shared affliction.

So don’t just focus on their flaws; think about your flaws too—and wherever there’s overlap, you might be able to earn some goodwill if you poke fun at your roastee and yourself at the same time. They’ll barely be able to tell it’s vehicular manslaughter if you also throw yourself under the bus.

One of my favorite examples of this is kind of a cheat, because it was done as a character. But when the faux conservative Stephen Colbert spoke at the 2006 White House Correspondents Dinner, just feet away from his subject, President George W. Bush, he did a “guys like us” line—and it built to maybe the most famous quote of his career.

“Guys like us, we don’t pay attention to the polls. We know that polls are just a collection of statistics that reflect what people are thinking in ‘reality.’ And reality has a well-known liberal bias.”

Assuming you are not roasting the architect of the Iraq War, though:

Soften the blow with the artifice of love.

Sometimes it’s funny just to take something that annoys you about your friend, and put it into the sentence structure “I love how you do X.” By using the tone and structure of praise, you can both lighten the intensity of whatever insult you’re making, and surprise your audience as you misdirect them at the very end of the joke.

One of the most artful executions of this approach I’ve ever heard came from Natasha Leggero at the Comedy Central Roast of James Franco, about the man of the hour:

“Acting! Teaching! Directing! Writing! Producing! Photography! Soundtracks! Editing! Is there anything you can do?”

Finally, once you’ve had enough of the fake love:

Close with actual love.

There’s a motto that originates from the Friars Club, one of the oldest private clubs in show business and the birthplace of the roast as we know it: “We only roast the ones we love.”

There’s a reason why it’s tradition for any roast to end with a moment of sincerity, when the roaster shares what the roastee means to them, and expresses genuine gratitude for their friendship.

It reminds everyone—the audience, the other roasters, and the person in the hot seat—that this is all in good fun. That any critical sentiments expressed are superseded by a deep, abiding love that can easily survive a night of snarky quips.

So don’t step away from the mic without setting aside the artifice for a moment, showing some vulnerability, and saying exactly why you feel close enough to this person to justify roasting them in the first place.

And then once you’ve done that you can throw in one more line about how they’re a huge asshole. Goodnight, everybody!