How To Tell A Story–Right Now–From A Master Of Improv

Upright Citizen Brigade founding member Matt Besser is one of the world’s leading improvers. Here, the off-the-cuff expert offers wisdom on how to free associate your way to solid spontaneous storytelling.

How To Tell A Story–Right Now–From A Master Of Improv

What we say matters a great deal, but so does what we don’t say. There are times when you just can’t afford to clam up when called upon to contribute. While it’s impractical to be forever armed with go-to stories on every conceivable topic—just in case your boss or a bridal party should parachute out of the sky, seeking your input—there are ways to prepare for off-the-cuff storytelling.


If anyone knows the ins and outs of speaking extemporaneously, it’s Matt Besser. Along with Amy Poehler and Adam McKay, Besser is one of the original members of Upright Citizens Brigade, the improv and sketch troupe that eventually launched a show on Comedy Central, several theaters and schools, and also the careers of everyone from Ed Helms to Aziz Ansari and Donald Glover. Besser also directed a movie recently, and he hosts a weekly improv podcast, called, simply, Improv4Humans.

One of the longest-running shows at the UCB theatre in New York and Los Angeles is called ASSSSCAT. Part of the show’s charm is that it relies on guests to recite monologues, which the theatre’s improvisers then parse through for details to use in their performance. The guest has no idea what topic he or she will be speaking about. As someone who has performed in and guided guests through literally thousands of such shows, though, Besser has rare insight into what can make or break an unprepared speech. Below are his tips for how to get through the high wire act of spontaneous storytelling, without letting the audience down.

Whatever Makes a Memory a Memory Makes It Interesting

Often when people don’t do so well in a monologue at UCB, it’s because they’re racking their brain so hard to be funny that they’re just not honest and don’t just tell a true story, which is what we want. A story is ultimately a memory. It’s important when you’re telling a story to think about why this memory is a memory. You don’t remember everything in life, you just remember certain things–so, why this one? Well, it’s because it was an atypical day, for better or worse. Something happened which makes that day stick out. So, whatever it is that makes it a memory, that’s what makes it interesting. That is ultimately the theme of the story.

When In Doubt, Free Associate

It’s important not to get too hung up on having a story that’s exactly on what you’re suggested to speak about. You can use it as inspiration or a launching point. I did my improv show earlier today and I asked for one-word suggestions from Twitter. So here’s one that fits what I was just saying: Pumpernickel. So, have I eaten pumpernickel bread? Maybe. Do I have a story on it? Definitely not. But if I need to start talking, I can’t just sit there and say “Pumpernickel… pumpernickel.” I can’t force myself to have a memory about pumpernickel if it doesn’t occur to me right away. So I have to free associate.

The most simple way to go here is bread, but I should probably try to be more specific, like “What kind of bread?” How about fancy bread? Oh, that makes me think of the deli that my dad would take me to when I was a kid over in Little Rock, Arkansas. So now I’m starting to launch into the story. I could just say my dad took me to a deli, but it’s more interesting to say that my dad took me to a deli in Little Rock, Arkansas, as opposed to New York. That’s another thing to look out for—details. Details make the story better.


So, my dad used to take us to the only deli in town, which also makes me think that we were basically the only Jews in town. We used to go to this deli, and we would get lox. Lox, that’s a very Jewish thing. I don’t think many other people in Little Rock had lox, or if they did, they called it smoked salmon, and that makes me think of the schoolgirl pickles we would get–which were these huge 8-inch pickles. Sometimes when you’re telling a story, especially if it’s a monologue on ASSSSCAT, it doesn’t necessarily have to have a beginning, middle, and end. I could just give a lot of details about being a half-Jew growing up in Arkansas, which would have sprung up from the word “pumpernickel.”

I can just give a lot of examples of that. So that’s not necessarily a story. Or I might just decide to, from that set-up, we go to the deli, I’m one of the only Jews–I could launch into a story about being uncomfortable about being a Jew in Little Rock. The one time the kids from class were talking about going on a ski trip, and I wanted to go to, but it was for Christian Young Life, which was a group I wasn’t a part of, and it made me feel sad, blah blah blah. That’s a true story. People aren’t always expecting you to have a great pumpernickel story in your back pocket.

Know When to Hold Back

There are two storytelling faux pas in my mind, like if you’re at a cocktail party or something. One is, “That’s not what we’re talking about.” We’ll be going around, telling stories about getting pulled over by the cops, and then it’s someone’s turn and they mention taking a driver’s test this week. Even if it’s an interesting story, um, can’t you see we’re in a groove here, telling pulled-over-by-the-cops stories? You’re not really being part of the group mind there. The other one is “Don’t follow a great story with one that is less than that.” Sometimes someone tells a story that can’t be followed. If the first pulled-over-by-the-cops story ends with, “Well, I wasn’t drunk, but I was high!” that could be a decent story. And if the next one is “I had no clothes on, and he had no idea,” that’s a little better, or at least keeps up with the last one. And then the next one is “I got pulled over for going 5 miles over the speed limit.” You have to realize that your story is a lot less interesting than the last two, and maybe you should have held onto it.

Watch Your Blind Spots (i.e., don’t be a jerk)

Sometimes people can be offensive and not even realize it. I guess that’s their personality kind of coming out, but people will say mildly racist stuff, like, “I pulled into Home Depot, you know, where the Mexican guys are always hanging out.” Even if there’s some element of truth to it, the way it sounds is racist. Some people get so caught up in fishing for details that they forget to think about how they’ll sound to whoever they’re audience is, and that’s a mistake. It’s funny how often that happens. Just about everybody has that blind spot, where it’s like, “Oh, we’re not supposed to say “Oriental food” anymore?”

If You Get Fuzzy On the Details, Admit It and Move On

You can always tell when people make shit up. It’s usually toward the end, because they can’t come up with an ending so they throw on some detail that makes you say, “What? Did that really happen.” I can always smell a dead fish there. So, to me, unless you know you have a bad memory, I think the story does the work. As you tell it, you should be pumping out memories and ideas. “Oh yeah, that was near my grandma’s house.” There should be a bunch of “Oh yeahs.” If the details aren’t coming, then they weren’t that interesting. The interesting and important details should be there. When I hit a foggy part where I can’t exactly remember what was said or what happened, I just say that. “I can’t remember what I said to that cop, but it was something like…” Sometimes when you say, “And I told that cop…” you’re like, “Really, you remember what you said to the cop.”


No Great Ending? Close With a Summation Or a Lesson

We all hate those stories that end with “And that’s the story.” There’s an expectation that you’ll have an interesting end, but life doesn’t always have such a storybook ending. If there’s more of a plot to the story, you have to at least have a plot point or a summation to end with. You might not have the ability to file away some detail for the ending, but as you’re telling the story, it’s like therapy, and you’re talking to yourself. Just look for the lesson or observation so that by the time you end your half-story, you can go, “I guess that’s what made me feel this way about these things.” Something about telling the story should lead to you forming an opinion, and you can always end with making that clear to your audience.