When I was at Upright Citizens Brigade, I would pretend to be a

Host:
The night hung low over Brooklyn, heavy with neon and the faint hum of subway rails beneath the concrete. The sky wasn’t black—it was bruised, the color of old wine and forgotten dreams. Inside a narrow comedy club, the stage lights flickered in tired yellow, casting long shadows across the floorboards that creaked like memory.

The room smelled of beer, cheap perfume, and the faint, stubborn hope of people still trying to be seen. Jack sat at the bar, his jacket slung over one shoulder, eyes fixed on the stage where a young comic fumbled through an act about dating apps. Jeeny sat beside him, stirring her drink slowly, the ice clinking like tiny bells of hesitation.

Behind them, a framed poster from the Upright Citizens Brigade hung slightly crooked, its edges yellowed, a ghost of laughter past.

Jeeny:
Bobby Moynihan once said, “When I was at Upright Citizens Brigade, I would pretend to be a sad, drunk rapper.”

Jack:
(smirking)
That’s not pretending. That’s art.

Host:
He said it with that half-grin, the kind that hides a wound behind a joke. The bartender, polishing a glass, looked up briefly as if he’d heard this kind of wisdom before—from drunks, actors, or both.

Jeeny:
(smiling faintly)
You’d think it’s just funny. But there’s something strangely truthful about it. Pretending to be sad and drunk—that’s what comedy is sometimes, isn’t it? Turning the ache into a punchline.

Jack:
Or hiding behind it. Everyone at those improv stages is just disguising pain in timing.

Jeeny:
Maybe. But there’s a kind of courage in that too. To turn your sadness into a character, to make people laugh at the thing that once made you cry.

Jack:
(laughs, low and sharp)
Courage? Or cowardice dressed up as performance? You’re not facing the pain; you’re just rehearsing it until it looks entertaining.

Host:
The lights on the stage shifted, washing the comic in a soft blue hue, as if the spotlight were confessing too. The crowd laughed, but the sound was hollow, delayed—like laughter that didn’t quite believe itself.

Jeeny:
Maybe the pretending is the only way some people can tell the truth. When you joke, you get to say what you really mean without anyone realizing it.

Jack:
Or maybe you say it because they won’t realize it. That’s the trick—disguise honesty in absurdity.

Jeeny:
That’s what Moynihan meant, I think. The “sad, drunk rapper” wasn’t about being funny—it was about revealing the sadness in disguise. Like how every clown knows laughter is just another kind of crying.

Jack:
(takes a slow sip of whiskey)
Maybe. But I’ve seen too many people hide behind the mask so long they forget what their own face looks like.

Jeeny:
(softly)
You sound like you’ve done that yourself.

Jack:
(grim smile)
Haven’t we all?

Host:
A pause settled between them. The crowd’s laughter washed over like a weak tide, then retreated again. Outside, a sirens’ wail cut through the night, its pitch rising and fading into the city’s pulse.

Jeeny:
You know, when I first read that quote, I thought it was about pretending. But the more I think about it, it’s about permission—the permission to feel broken in public, as long as you make it entertaining.

Jack:
That’s what people love about comedians—they bleed in rhythm. If the timing’s good enough, the audience claps instead of flinching.

Jeeny:
And maybe that’s the only way some people can be loved—by turning their pain into something others can digest.

Jack:
(nods slowly)
That’s the irony. You have to perform your sadness to make it acceptable. But if you actually show it—if you’re genuinely sad—they call you self-indulgent.

Host:
His voice carried the weight of something lived, not theorized. The bar light caught in his eyes, reflecting a dull, gold glimmer like the last flicker of a dying stage light.

Jeeny:
You ever wonder what happens after the show? When the lights go down and the audience goes home?

Jack:
That’s when the real act begins. The “I’m fine” act. The “it was just a joke” act.

Jeeny:
(leans in)
You sound like you’ve worn that costume a long time.

Jack:
We all have. Life trains you for improv—you just never know what scene comes next.

Host:
The comic on stage finished with a flourish, bowed, and the crowd cheered, a brief storm of hands and sound before the silence returned, louder than before. The bartender turned down the lights, the edges of the room melting into a comfortable dimness.

Jeeny:
You know what I think? Pretending to be a sad, drunk rapper isn’t about performance. It’s about confession—disguised as a laugh.

Jack:
(half-smile)
So sadness becomes an art form, huh?

Jeeny:
Sadness always was an art form. Comedy just put a beat to it.

Jack:
And the “drunk” part?

Jeeny:
(grinning)
That’s just honesty in liquid form.

Host:
Jack laughed, a real laugh this time—unpolished, unrehearsed. It echoed in the empty space, as if the walls themselves were relieved to hear something true.

Jack:
So maybe what Moynihan was saying is that we’re all just pretending to be something enough times until the pretending feels like living.

Jeeny:
Yes. But the trick is not to forget the pretending is pretending. Once you start believing the act, you’re lost.

Jack:
(quietly)
And if you stop pretending?

Jeeny:
Then the curtain falls. And you’re just left with yourself.

Host:
The bartender dimmed the last of the lights, leaving only the neon glow from outside spilling in through the door—pink, blue, tired. A faint buzz filled the air, like the echo of laughter long gone.

Jeeny:
You ever think maybe we all have our own “sad, drunk rapper” somewhere inside us?

Jack:
What, the part that turns loneliness into rhythm?

Jeeny:
No. The part that still wants to be heard, even when it’s pretending not to care.

Jack:
(leans back, voice low)
Yeah. Maybe that’s the only part that’s real.

Host:
Outside, the city exhaled—cars, voices, light—all blending into a single tired melody. Inside, Jack and Jeeny sat in their corner, two souls in a half-lit room, surrounded by the echoes of other people’s laughter.

For a long moment, they didn’t speak. The silence wasn’t awkward—it was honest. The kind that follows a performance and feels more sacred than applause.

Then Jack raised his glass, and Jeeny followed.

Jack:
To pretending—until it feels true.

Jeeny:
(smiling)
And to knowing when to stop.

Host:
They clinked glasses, and the sound rang through the room like a small truth caught between loneliness and laughter.

Outside, the rain began again—soft, rhythmic, almost like a beat.
Somewhere deep in the city, a rapper’s voice rose from a basement, slurred but earnest,
half sad, half alive—
and maybe, just maybe,
a little bit free.