DEATH OF AN UMBRELLA SALESMAN — Won’t Anyone Buy An Umbrella From This Man? Please?

Chris Hadley
May 23, 2018 · 7 min read
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While door-to-door salespeople are as much of a relic as they are a nuisance, filmmaker Steve Herold’s intriguing comedy short film Death of An Umbrella Salesman represents how a hapless yet persistent umbrella peddler named Stanley Grimp (played by Kevin Kolack) will do whatever he can — and then some — to convince people to buy his fancy portable canopies. With Stanley’s ex-wife demanding all the dough he can cough up to pay for her post-divorce financial needs, will he ever cash in on his slipping business?

Directed by Herold, Death Of An Umbrella Salesman co-stars Sabrina Gennarino (The Walking Dead) as Stanley’s latest customer, Betsy May Morgan. As Stanley pulls out all the stops to persuade Betsy to purchase his product, the desperate merchant is surrounded by a bizarre mix of selfie-takers and mail-order delivery men. Stanley also meets a depressed man (“Suicidal Guy” played by Robert Castiello) who’s got it just as bad as the divorced umbrella salesman does.

Death Of An Umbrella Salesman was recently presented to a sold-out audience in April at the Louisiana International Film Festival in Baton Rouge, La. Incidentally, Casiello also has a small role in director Ethan Hawke’s acclaimed musical docudrama Blaze, which played at the festival on April 19th. (More on that ahead.)

Shot in Louisiana and parts of New Jersey, the film’s concept came from an amusing story that involved — of course, umbrellas. That story, though, involves Herold’s discovery of some peculiar excess baggage that he saw in the rear compartment of an acquaintance’s vehicle. During the festival, Herold and Casiello talked about their memories of making Death Of An Umbrella Salesman.

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Kevin Kolack plays the desperate door-to-door umbrella peddler Stanley Grump in director Steve Herold’s hilarious short DEATH OF AN UMBRELLA SALESMAN.

Discuss the inspiration for Death Of An Umbrella Salesman.

Herold: The idea for the film came from me driving a friend and his wife to the airport in their car. When I dropped them off, they asked if I could bring their car back and leave it at their house. When we got to the airport, they went to get their luggage out of their trunk. Inside, there were like 10 or 12 umbrellas.

If most people have one umbrella, it’s a miracle. My friend had 10 or 12, and I was like, “why do you have all these umbrellas? What are you, an umbrella salesman or something? What is the deal?” It was a stupid joke, but the idea stuck. That looked like it would be the trunk of a door-to-door umbrella salesman, to me. Nobody ever asks me “why did he have all those umbrellas?” Honestly, I’m glad nobody asked me because I don’t know! I didn’t ask!

What was the casting process like?

Herold: I had worked with Kevin and Sabrina before on a couple of other films. When we were shooting in Baton Rouge, Kevin lives in New York. He had to fly in. Sabrina lives in New Orleans, so that was no problem. The minute I realized we were going to do this, the first call I made was to her to see if she was interested in doing it. It’s always a blast to work with her.

Rob (Casiello) came from Tanner Short, our associate producer, who’s working with me locally in Baton Rouge. I asked him, “do you have any actors? We need this guy to play this one part,” and he said “my buddy Rob is an actor.”

He pulled up a clip on his phone of a funny performance that Rob had done, and I was like, “call him up.” The other cast members were found through people I knew. I didn’t have auditions. They sort of came to me through referrals.

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Talk about the process of making Death Of An Umbrella Salesman.

Herold: The reason why we were shooting it in Baton Rouge was because I was working on a TV show called Killing Fields for Discovery. We did the first season in Baton Rouge, and then we came back down to do the second season. I knew we were going to be here for 5 or 6 months.

We have our weekends off, so I decided since we’re down here it would be interesting to shoot it in Baton Rouge, which is a new location for me since I’m not from here (I’m from New Jersey). It would be interesting to shoot it here, and to try to capture a little bit of the local flavor.

We shot in Baton Rouge for 4 days (2 weekends), and did some shooting out in Port Allen, as well. Then we shot in 2 days in New Jersey for some stuff and locations that, for logistical reasons, we couldn’t find here in Baton Rouge. My goal was to do everything here, but there were just 1 or 2 things that I couldn’t do here.

Jessica Gurney, who shot the film, was someone I knew. She was working up in northern Louisiana on Duck Dynasty. I called her up and said, “hey, we’re shooting this thing. We need a director of photography.” She came down and she brought gear from that show.

The sound guy, Steven McRoberts, was sort of like the only guy who I didn’t really know. I hired him. He’s out of Dallas. The shoot went well. It was a small crew, but everybody had a good kind of rapport. Everybody worked really hard, and I think we did a fairly good job.

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Frazzled umbrella salesman Stanley Grump (Kevin Kolack) trudges toward his latest house call in the comedy short film DEATH OF AN UMBRELLA SALESMAN.

Robert — in addition to your role in Death Of An Umbrella Salesman, you also have a small role in Blaze as a bartender. What was it like working on both films?

Castiello: It’s in a real brief scene in a Chicago bar, but filming that was a great experience, It’s a few lines in the movie, but the experience of being directed by Ethan Hawke and getting to do some improv was really enjoyable. We shot for a half a day, for hours and hours and hours.

Ben Dickey (who plays Blaze) and I were acting lines, heckling each other back and forth. His performance is just mind-blowing. He was so good in that movie. He definitely deserves his Sundance accolade that he got. I loved working with Ethan Hawke, and with everybody, including (co-screenwriter) Sybil Rosen, as well. It was a great experience on that film.

I had a great experience working with Steve and the whole team there on Death Of An Umbrella Salesman. We had a lot of fun. I didn’t shoot that long with him, but I enjoyed it! It was a blast! Obviously, it was a little different experience because you’re making straight up comedy.

I love comedy, too. I love serious acting, but I love comedy. Normally, people want to cast me as the Devil, or a serial killer, or a mobster, but Steve saw through that and he said, “no, I want him in comedy,” but he made me a suicidal nut job. Still, it was comedy, right?

Steve, describe your memories of working with Robert on Death Of An Umbrella Salesman.

Herold: My best takeaway from how good Rob was, and how on point his performance was, was that I’ve been posting some little “behind-the-scenes” videos from the film on YouTube. I made a couple of blooper and outtake things, and I had none of Rob! I had no mess-ups, or whatever. Every take of Rob’s was spot on, and I felt bad because I wanted all of the cast members to be represented. I ended up putting a little piece in, but I was like, that’s how good he was. I didn’t even have any mistakes or flubs to use.

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L-R: Umbrella salesman Stanley Grump (Kevin Kolack) begs customer Betsy May Morgan (THE WALKING DEAD’s Sabrina Gennarino) to buy his product in DEATH OF AN UMBRELLA SALESMAN.

Besides the fact that you want people to laugh out loud at Death Of An Umbrella Salesman, is there anything you want viewers to take away from the whole experience of watching the film?

Herold: Because it’s a comedy, it’s really a case of satisfaction, and of an audience getting it. When it plays, and when the jokes work, and when you get a laugh out of people, it’s just satisfaction. This film probably took a good year and a half to make from start to finish, and you don’t know. On this level, we don’t have test screenings. I’ve got friends and other filmmakers who I can go to and say, “take a look at this, let me know what you think” with different cuts of the film.

Until it’s there in front of an audience, you just don’t know. When you go into a festival, it screens and you get the laughs because in this case, it’s a comedy. It’s just satisfaction. At the same time, for me it’s not a completely selfish thing.

From my point of view, I’m happy for my actors and the crew, who were all great and who worked very hard. For me, I get satisfaction in knowing that I didn’t fail the actors, and that they did a great job. They worked hard and I didn’t mess it up. They’ve got a performance in a film that they were in that they can also be proud of.

Casiello: If you see a really desperate guy out there trying to sell you umbrellas, buying one might save his life!

Here’s the trailer for Death Of An Umbrella Salesman:

For more information about Death Of An Umbrella Salesman, visit the film’s web page:

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