Roasting 101: 5 Tips for Being Playfully Savage

Roasting is an art. When done well, it’s hilarious, clever, and leaves everyone laughing, including the person being roasted. But when done poorly, it can come off as mean-spirited or just plain cruel. In my view, the key to a great roast is striking the right balance between sharp and playful. Here are five tips that come to mind when I reflect on roasting.

First, to borrow some language from Jared Volle and Greg Dean: be playfully mean. A roast is supposed to poke fun, not wound. Now, don’t get me wrong: It will have some truth in it, which is much of what makes it funny. But it’s about exaggerating the truth of someone’s or something’s quirks or flaws in a way that’s obviously not too serious. I like to describe it as throwing soft punches that look hard. Put another way: You want the person you’re roasting to laugh and think, That’s funny because it’s true, not Wow, that was uncalled for. For that to happen, it has to be lighthearted and clever, not personal or nasty.

Second, only roast people who are willing to be roasted. Not everyone is comfortable being the target of a joke, and that’s okay. If someone isn’t open to being roasted, move on. The best roasts happen when both sides are in on the joke. That’s why you see folks like Jeff Ross and David Lucas bringing people who “agree” to be roasted up on stage. It’s a form of mutual trust—if someone lets you roast them, they’re giving you permission to playfully push their buttons like you do with friends. And that can be really fun.

Third, only roast the ones you love—or at least respect. Jeff Ross, the Roastmaster General himself, says this all the time and has a book about it. A great roast comes from a place of affection or admiration. You’re making fun of someone, but the subtext is, I like you enough to roast you. I’ve long said to my kids: You know I love you if I crack jokes about you. That might seem odd, but in my case it’s true. It’s true with them and really anyone in my life. Roasting is, in a way, a love language, as crazy as that might sound. But that goes the other way, too, because if there’s no love or respect behind the jokes, it will feel more like an attack than a roast. The best roasts celebrate the person even as they knock them down a bit.

Fourth, use comparisons and analogies. These are your bread and butter when it comes to roasting. Start with “look like,” “sound like,” or “dress like.” For example: “You look like… an extra from a Walmart training video.” Analogies are funny because they’re visual, immediate, and specific. The more absurd or unexpected the comparison, the better. But as with all things in comedy, I think it’s best if you can keep it clean and clever—there’s no need to be vulgar or lazy.

Finally, welcome roasts in return and be willing to roast yourself. Roasting is a two-way street. If you’re dishing it out, you have to be ready to take it, too. In fact, the best roasters are the ones who can laugh at themselves. Self-deprecating humor can be a great way to break the ice and show that you’re not taking yourself too seriously. It also sets the tone for the roast—if you can laugh at yourself, the person you’re roasting will feel more comfortable laughing at themselves, too. For example, the picture of me for this post is a little odd; I believe I had just told a joke and didn’t get many laughs. I could roast myself by saying: My friend took a picture of me while I was up in front of everyone, but I was looking down… imagining myself in a casket. That’s a little dark but, oh well. It’s funny because it’s there’s some truth to it. Was I thinking of a casket or imagining myself in one? No. Was I looking down? Yes. Anyway…

Roasting is one of the most entertaining forms of comedy when done right. It’s about playful jabs, clever wordplay, and mutual respect; roasting is a celebration of what makes each person uniquely roastable. Now, take a minute to admit you’re an idiot for reading this blog post then remember, at least you're not the one who wrote it.