The Death of an Umbrella Salesman


OSCAR: A well-dressed man in his 30’s adorning a grey jacket and horn-rimmed glasses. His shoes are shined and the knot on his blue and pink striped tie is perfectly executed. His clothes are pressed and his hair is parted. He has bags under his eyes, however, and his wrinkles have started to extend from his lips.

MAC: A man in his early 60’s wearing the same outfit as Oscar – grey jacket, candy tie, and glasses – but disheveled and wrinkled. His collar is flat, and his grooming leaves much to be desired. His portly body seems held together by a belt that is much too tight.

SECURITY GUARD: Security personnel at the Hermes store. He wears a suit and tie.

BUSINESS MAN: A man in his 40’s in suit and tie with an iced coffee in hand and phone up his ear.

GLORIA: A young woman in her late 20’s wearing a sun dress and big sunglasses.

NEW CUSTOMER: A generic man in his 50’s walking through the French Quarter.

THIRD CUSTOMER: A tourist in his 50’s.


[SCENE: Oscar’s Fashionable Umbrellas is an umbrella kiosk on Magazine Street in New Orleans. The stand is stacked high with umbrellas of every color and size, handle and pattern. It is a fashionable street, with the storefronts of Hermes, Coach, and other luxury brands filling the block. OSCAR scurries around the stand, re-arranging each umbrella to his liking, while MAC looks on. The SECURITY GUARD leans against the Hermes store door whistling and staring at his phone.]

OSCAR: I have to focus today. No distractions.

MAC: You won’t regret having me here. I can feel a sale on the horizon.

OSCAR: You say that every day.

MAC: Oscar – you must start each sales day with a positive attitude. If there’s one thing I learned it’s that no sale starts with negativity.

OSCAR: We’re late. I hate being late.

MAC: We’re hardly late. The Hermes store has only been open a few minutes.

OSCAR: We can’t open after then. They already out-prestige us with their bourgeois security personnel.

[OSCAR and MAC both stare at the SECURITY GUARD who stops looking at his phone to wave. OSCAR flicks him off.]

MAC: Let’s take attendance shall we? Start off the day right. [he pulls a clipboard from the stand.] Oscar, owner and proprietor, accounted for. Mac, head of sales and senior mentor, accounted for as well.

OSCAR: [with sarcasm, continuing to arrange the umbrellas] I’m glad you have that covered.

MAC: [taking a step back from the stand to get more perspective] Oh, I forgot something.

[MAC pulls out a hand-painted wooden sign from under the stand that says “Oscar’s Umbrellas” and places it near the top. Oscar pulls it down.]

OSCAR: What is this?

MAC: I painted it for the stand. To help give it a little pizzazz.

OSCAR: No, absolutely not.

MAC: Why not? I like it. I think it will help. Right now, the stand is missing that extra something.

OSCAR: First off, umbrella is spelled wrong here. There are two L’s. Second of all, this painting of an umbrella – did you do this?

MAC: Yes.

OSCAR: It looks like a penis. It’s at least questionable.

MAC: I think your mind is in the gutter. [holding the sign up] I admit painting isn’t my strong suit. We all have weaknesses. I’m more here to head the sales process anyhow.

OSCAR: I wanted to talk to you about that. For the first few customers, why don’t you let me do the talking, and maybe you can take some customers later in the day.

MAC: Nonsense! I will take the first customer as I am the most seasoned salesman.

OSCAR: I’m not kidding. We can’t –

MAC: I’ve been a salesman in this town my entire life. I sold…

OSCAR: [interrupting] Pineapples.

MAC: … Pineapples to feed my family for…

OSCAR: [interrupting] Twenty.

MAC: Twenty-five years. I’ve seen your collection of books in your car. The books on sales. Let me explain something to you, Oscar. No book is going to tell you how to make sales. It’s in your blood. That’s why you lost your lease to the Hermes store.

OSCAR: I lost the lease to the Hermes store because the City doesn’t protect local businesses.

MAC: Forget about that. Here’s your biggest sales issue that I’ve seen. Are you ready? You’re too uptight. Loosen up!

[MAC tries to help OSCAR stretch his arm but flexes it awkwardly.]

OSCAR: Stop that! That’s awful! Who told you to stretch like that?

MAC: You’ll figure it out eventually. The great salesman is flexible. Write that down.

OSCAR: I’m not going to write it down.

MAC : Well, let it wash over you like a life lesson then. Because it certainly is. [He continuing despite Oscar rolling his eyes] It’s a balance though. Because comfort is also the enemy of the great salesman. If you’re trying to sell to someone, you need them to think that if you don’t make this sale, your family doesn’t eat tonight. People respect people who are out on their last limb.

OSCAR: That doesn’t make any sense.

MAC: Think of it this way: if you’re so comfortable, why are you out here trying to sell umbrellas? People will think you’re a sociopath. They’ll think to themselves – why is this lunatic out here on a Sunday morning if he’s so comfortable? Write this down too.

OSCAR: I’ll just let this one wash over me.

MAC: Another issue I’ve seen with your sales technique – you’re too nice. You have to be almost a jerk. Otherwise, why is anyone buying from you? Graze that line between nice guy and complete piece of shit. That’s the sweet spot in sales.

[The BUSINESS MAN enters stage right and walks past the stand briskly, not turning to recognize OSCAR or MAC.]

MAC: Watch, I’ll show you. [He approaches the business man] Hey you! What’s your interest in one of our fine umbrellas here?

BUSINESS MAN: [not breaking stride] None.

MAC: [following the BUSINESS MAN] None? They’re hand crafted, made by one of the great umbrella auteurs of his generation. Wouldn’t you look fashionable in this beautiful umbrella here?

BUSINESS MAN: I’m alright.

MAC: You’re not from around here I see. Don’t know of Oscar’s umbrellas, perhaps?

BUSINESS MAN: I’m not, and no I don’t.  

MAC: [changing demeanor] You’re not a man of fashion I can see that. The unmatched belt and shoes tells a greater story than anything else. I’m offering you a chance to look slightly less foolish in a fashionable district such as this.

BUSINESS MAN: Really, I’m alright.

MAC: Alright, but let me ask you this – how stupid are you going to look if it starts raining? People are going to think – hey look at this idiot. No umbrella. Wow – how dumb could he be? [A brief pause as MAC attempts to gauge the BUSINESS MAN’s reaction] I’m not kidding. You’re caught in between a rock and a hard place – unfashionable and stupid. What girl would want you?

[The BUSINESS MAN opens the lid of his iced coffee and throws it on MAC. OSCAR puts his head in his hands. The SECURITY GUARD at the Hermes Store laughs. MAC returns to the stand, wiping his face with his jacket.]

MAC: He said he might stop by on the way home.

OSCAR: You’re not allowed to talk to anyone else.

MAC: What? That’s crazy. That guy –

OSCAR: [interrupting] Probably would have bought an umbrella from me.

MAC: He was a yuppie. I can’t be expected to sell to them. I –

OSCAR: [Interrupting] Wait, stop!

[OSCAR’s focus turns to GLORIA, as she enters stage right, passing the umbrella stand. Both MAC and OSCAR watch her as she crosses the stage and exits stage left.]

MAC: I meant to tell you – I’ve done some research on her.

OSCAR: What? Why?

MAC: Checked out the building she goes into down the street It’s home to a dentist’s office and a psychiatrist.

OSCAR: So what?

MAC: So your dream girl either has bad teeth or mental problems. Both are red flags.

OSCAR: Or she works there.

MAC: I didn’t consider that. [Pausing for thought] Why didn’t you try to sell her an umbrella?

[OSCAR shakes his head. As he turns, a NEW CUSTOMER enters stage right and walks past the umbrella stand. OSCAR attempts to run his down.]

OSCAR: Excuse me sir. Would you like to buy an umbrella?

The NEW CUSTOMER lifts his arm to say no and keeps walking. Oscar turns back to the stand in frustration.

OSCAR: [Talking to himself] You can do this, just be calm.

MAC: Oscar? [MAC keeps pestering as OSCAR ignores him] Oscar? [Another beat] Oscar?

OSCAR: What?

MAC: You shouldn’t show frustration like that. It’s not becoming to the customer.

OSCAR: I know that! Did you learn that selling pineapples thirty years ago? Did they tell you that they day you had to close the warehouse and you had to come work for your nephew selling umbrellas on Magazine Street.

MAC: It was avocados. We sold avocados.

OSCAR : It would be helpful if you would stop talking.

MAC: Alright. You’re a little frustrated. I’ll let you cool off.

[MAC and OSCAR meander around the umbrella stand for a few moments. MAC tries to stretch he gave to OSCAR earlier and recoils at the pain he inflicts on himself.]

OSCAR: [Quietly] She works at the dentist’s office.

MAC: How do you know?

OSCAR: That’s why I chose this spot. [Sighing] In the insane hope that at some point there will be so many people surrounding this stand that she will find her way through the crowd to buy just one.

MAC: Then what?

OSCAR: Then we’ll talk and who knows. Anything could happen.

MAC: [Nodding slowly] I think you’re wasting your time.

OSCAR: [With a sarcastic laugh] Alright.

MAC: I think you should try and sell her an umbrella. She works at a dentist’s office. She doesn’t look like she’s from here. Looks like one of those hipsters. People from out of town love this quirky shit.

OSCAR: Maybe.

[A THIRD CUSTOMER walks past the stand from right to left. Oscar flags him down.]

OSCAR: Excuse me sir. Are you interested in buying an umbrella?

THIRD CUSTOMER: I have an umbrella.

OSCAR: Yes, but these are very fashionable. And you never know when you will need a second umbrella.

THIRD CUSTOMER: [Stopping to look at the designs and patterns of the umbrellas] You designed all of these?

OSCAR: I did. Is there one you would like to see?

THIRD CUSTOMER: I like the blue one, with the white clouds?

OSCAR: [Pulling the umbrella out of the stand] This one?


OSCAR: Yes, I like this one as well. It’s fun but not too crazy for someone like you.


OSCAR: Thirty –

[As OSCAR responds, GLORIA walks from right to left of stage towards the stand. OSCAR becomes distracted.]

MAC: [Swooping in to protect the sale]: It’s thirty dollars. I can help you over here if this is the one you would like?


[OSCAR turns to the stand, taps his fingers on a few umbrellas before choosing a purple and yellow striped umbrella and walking over to GLORIA.]

OSCAR: Miss!

[The lights focus on OSCAR and GLORIA and the stage is silent. OSCAR speaks to GLORIA and does a small dance with the umbrella, showing off its patterns and pointing to certain features. She smiles and laughs but eventually puts her hand out and starts walking away. OSCAR calls out to her one more time and seems to sheepishly ask her something. She cackles with laughter and walks off stage. We hear her final laughter off screen. OSCAR returns to the umbrella stand where MAC is finishing the transaction with the THIRD CUSTOMER.]


[OSCAR sits on a curb next to the umbrella stand. He throws his hands through his hair, messing it up for the first time. He loosens his tie. MAC sits on the curb next to him.]

OSCAR: She liked it but – perhaps it’s not for her.

[MAC pulls a pack of cigarettes out of his pocket and puts one in his mouth and lights up. He offers one to OSCAR who accepts.]

OSCAR: Fuck this. Fuck this City. Fuck Hermes and fuck having to sell to these tourists.

[A long beat as they smoke their cigarettes]

MAC: I’ve always hated sales, you know.

OSCAR: Right, sure.

MAC: I’m serious. Always thought it was horrible, but what could I do? Being born into an pineapple empire as I was.

OSCAR: What did you want to do?

MAC: (Staring at the pavement) I really wanted to be painter.

OSCAR: I’m sorry I insulted your sign. But it did look like a penis.

MAC: It does. I just didn’t see it.

OSCAR: Why didn’t you do it then? Paint?

MAC: I told my dad and he said that it was a great idea, but I would have to be accepted into a gallery before he would allow me to quit. So I decided to paint a sinking ship. I had seen one when I was a child and I knew what it would look like. And I tried painstakingly to get it just right. I painted probably one hundred versions but I always made some mistake. Something was always just a little bit wrong. I was never accepted. But I kept trying and trying. I knew that if I just got it right once, everything would change. But eventually my room filled with these failed paintings of this sinking ship. And my dad came home one evening – drunk as all hell – and asked me, “how can someone spend so much time surrounded by such failure?” (MAC takes a long drag of the cigarette) He didn’t mean it, but it’s clear sales was in my DNA. Not art. Certain things you can’t change no matter how hard you try.

[OSCAR and MAC sit for a moment staring at the pavement, before OSCAR stands and walks off stage. He returns with a carton of eggs and hands one to MAC, who looks at him inquisitively. OSCAR puts the carton on the sidewalk and grabs one, then launches it at the Hermes store.]

MAC: Oscar! Yes! You son of a bitch.

[MAC grabs an egg himself and throws it at the store. The SECURITY GUARD stirs and starts across the street]


MAC: Oh shit, Oscar, come on!

[OSCAR and MAC run off stage, the SECURITY GUARD chasing them. They run back and forth on and off stage with the SECURITY GUARD in pursuit. Finally they return to stage and the SECURITY GUARD isn’t right behind them. They are breathing heavy, hands on head. MAC laughs and slaps OSCAR on the back. OSCAR smiles, and as they stand next to the stand, it starts to rain.]

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