How to Craft the Perfect Comeback, According to Experts

In a 1997 episode of Seinfeld called “The Comeback,” George Costanza is merrily stuffing himself with free shrimp at a meeting. His coworker mocks him: “Hey, George, the ocean called. They’re running out of shrimp.” George stands humiliated as laughter fills the room, his mind searching frantically for the perfect riposte.

It’s only later, on the drive home, that he thinks of the comeback. But the moment has passed.

The common human experience of thinking of the perfect response too late—l’esprit de l’escalier, or "the wit of the staircase"—was identified by French philosopher Denis Diderot when he was so overwhelmed by an argument at a party that he could only think clearly again once he’d gotten to the bottom of the stairs.

We've all been there. Freestyle rappers, improv comedians, and others who rely on witty rejoinders for a living say their jobs make them better equipped to seize the opportunity for clever retorts in everyday life. They use a combination of timing, listening, and gagging their inner critics. Here are their insights for crafting the perfect comeback.

LISTEN TO YOUR OPPONENT’S ARGUMENT.

The next time you’re in a heated conversation, be less focused on what you're about to say and more attentive to what you're actually responding to. When you spend more time considering what your sparring partner is saying, “you’re deferring your response until you’ve fully heard the other person," Jim Tosone, a technology executive-turned-improv coach who developed the Improv Means Business program, tells Mental Floss. Your retorts may be more accurate, and therefore more successful, when you’re fully engaged with the other person’s thoughts.

DON’T THINK TOO MUCH.

According to Belina Raffy, the CEO of the Berlin-based company Maffick—which also uses improv skills in business—not overthinking the situation is key. “You’re taking yourself out of unfolding reality if you think too much,” she tells Mental Floss. It’s important to be in the moment, and to deliver your response to reflect that moment.

TRAIN THAT SPONTANEOUS MENTAL MUSCLE.

History’s most skilled comeback artists stored witticisms away for later use, and were able to pull them out of their memory at the critical time.

Winston Churchill was known for his comebacks, but Tim Riley, director and chief curator at the National Churchill Museum in Fulton, Missouri, tells Mental Floss that many of his burns were borrowed. One of his most famous lines was in response to politician Bessie Braddock’s jab, “Sir, you are drunk.” The prime minister replied, “And you, Bessie, are ugly. But I shall be sober in the morning, and you will still be ugly.”

Riley says this line was copied from comic W.C. Fields. Nevertheless, it took quick thinking to remember and reshape the quote in the moment, which is why Churchill was thought of as a master of timing. “It was an off-the-cuff recall of something he had synthesized, composed earlier, and that he was waiting to perform,” Riley says.

But in some situations, the retort must be created entirely in the moment. Training for spontaneity on stage also helps with being quicker-witted in social situations, New York City battle rap emcee iLLspokinn tells Mental Floss. It’s like working a spontaneous muscle that builds with each flex, so, you’re incrementally better each time at seizing that witty opportunity.

MUZZLE YOUR INNER CRITIC.

Anyone who has been in the audience for an improv show has seen how rapidly performers respond to every situation. Improv teaches you to release your inhibitions and say what drops into your mind: “It’s about letting go of the need to judge ourselves,” Raffy explains.

One way to break free of your internal editor might be to imagine yourself on stage. In improv theater, the funniest responses occur in the spur of the moment, says Douglas Widick, an improv performer who trained with Chicago’s Upright Citizens Brigade. By not letting one’s conscience be one’s guide, actors can give into their “deepest fantasies” and say the things they wouldn’t say in real life.

IF YOU HAVE AN EXTRA SECOND, HONE YOUR ZINGER.

The German version of Diderot’s term is Treppenwitz, also meaning the wit of the stairs. But the German phrase has evolved to mean the opposite: Something said that, in retrospect, was a bad joke. When squaring up to your rival, the high you get from spearing your opponent with a deadly verbal thrust can be shadowed by its opposite, the low that comes from blurting out a lame response that lands like a lead balloon.

That's a feeling that freestyle rapper Lex Rush hopes to avoid. “In the heat of the battle, you just go for it,” she tells Mental Floss. She likens the fight to a “stream of consciousness” that unfolds into the mic, which leaves her with little control over what she’s projecting into the crowd.

It may help to mull over your retort if you have a few extra seconds—especially if you’re the extroverted type. “Introverts may walk out of a meeting thinking, ‘Why didn’t I say that?’ while extroverts think, ‘Why did I say that?’” Tosone, the improv coach, says. Thinking before you speak, even just briefly, will help you deploy a successful comeback.

And if it doesn’t go your way, iLLspokinn advises brushing off your missed opportunity rather than dwelling on your error: “It can be toxic to hold onto it."

THROW DIGITAL SHADE ACCORDING TO THE SAME RULES—BUT BE QUICK ABOUT IT.

Texting and social media, as opposed to face-to-face contact, give you a few extra minutes to think through your responses. That could improve the quality of your zinger. “We’re still human beings, even on screens. And we prefer something that is well-stated and has a fun energy and wit about it," Scott Talan, a social media expert at American University, tells Mental Floss.

But don't wait too long: Replies lose their punch after a day or so. “Speed is integral to wit, whether in real life or screen life,” Talan says. “If you’re trying to be witty and have that reputation, then speed will help you."

Some companies have excelled in deploying savage social media burns as marketing strategies, winning viral retweets and recognition. The Wendy’s Twitter account has become so well known for its sassy replies that users often provoke it. “Bet you won’t follow me @Wendys,” a user challenged. “You won that bet,” Wendy’s immediately shot back.

George Costanza learns that lesson when he uses his rehearsed comeback at the next meeting. After his colleague repeats his shrimp insult, George stands and proudly announces, “Oh yeah? Well, the jerk store called, and they’re running out of you!”

There’s silence—until his nemesis comes back with a lethal move: “What’s the difference? You’re their all-time best-seller.”