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Rising Stars: Meet Jesse Pimpinella

Today we’d like to introduce you to Jesse Pimpinella. 

Alright, so thank you so much for sharing your story and insight with our readers. To kick things off, can you tell us a bit about how you got started?
Growing up, I became obsessed with stand-up comedians like Ron White, Robin Williams, and Christopher Titus. I was baffled that there was a career where you could talk, tell stories and make people laugh. Once I became 18, I began to do open mic shows every night. From there, I got the attention of the local comedy clubs and began to work weekends with headliners from Comedy Central, HBO, and Netflix. Through great friends and mentors, like comedian Johnny Lee Dam, I began to tour the Midwest and headline shows. On October 1st, 2021, I released my debut comedy special & album, “Jesse Pimpinella: Hot Mess” through Eloop Media LLC, which became a #1 hit on Amazon.com during its opening weekend. Currently, I’m still touring, while hosting a weekly show called at The Grown-Ups Table with my friend John Jacobs. When I am not on the road, I am relaxing at home with my wonderful and supportive wife and our two dogs, Gizmo and Sidney. 

Alright, so let’s dig a little deeper into the story – has it been an easy path overall, and if not, what were the challenges you’ve had to overcome?
Trust me, there was no smooth road. But that’s what makes it so challenging and fun. When you start out, you just have to get on stage and get your hands dirty. Failure is a vital to your future success. Accept failure and embrace it because you will learn so much and come back stronger from it every single time. In the beginning, there were nights where there was no laughs. Not even a chuckle. When a joke falls flat, the silence of the audience would make my stomach turn. After, I would go home and watch a video of my performance to see what I can do to improve that joke and prevent it from falling flat. Eventually, you become more confident at writing and performing that you won’t go through too much trial and error to whip a joke into shape. 

Besides failure in comedy, you may feel the wrath of insecurity and jealousy from others comedic peers. During my early years, I did not fit in with the local comedy scene. I was told that I was not funny, and that comedy was not for me…” Fast forward to today, I am on the road doing stand-up most weekends, my comedy special/album, “Jesse Pimpinella Hot Mess” was #1 on Amazon, and I have an incredible team of comedians that I work with on podcasts, short films, and more. Once you accept failure is the key to success, the fun shall begin. 

As you know, we’re big fans of you and your work. For our readers who might not be as familiar what can you tell them about what you do?
As an independent stand-up comedian, my career splinters into three areas: management, writing, and performing. About 90% of my career takes place off stage. Here is what I mean, as a manager to myself, I am responsible for booking shows for myself, promoting shows, creating a following online, and arranging travel for my tour. There are some days where I am just sending emails and calling venues about booking me for a comedy night/weekend. As a writer, I am responsible for constantly creating new jokes and refining current jokes make it funnier. Finally, as a performer, I am responsible for making the audience laugh and making sure they had a great time. It is so important that my audiences have a great time because, with the world we live in today, there are endless options for what they could have done instead of seeing a comedy show. They could stay in and binge-watch something on Netflix, go to a nightclub, go see a movie, etc. Therefore, if you choose an evening of comedy with me over all the other options, then get ready because I am going to give you my best show each and every time. 

I am most proud of the fact that my debut comedy special/album, “Jesse Pimpinella: Hot Mess” became a #1 hit on Amazon and also won Best Monologue at the Muddy Crab Film Festival. Currently, through Eloop Media LLC, I am in development for my second comedy special. 

Have you learned any interesting or important lessons due to the Covid-19 Crisis?
I have learned that it is vital to adapt and stay in touch with you audience. Being in a club every weekend, allowed me to be very present with my audience. But when lockdown hit us back in March 2020, comedy was put on hold indefinitely. That is why social media like TikTok became even more important for comedians; it was a direct line to our audience. During that time, I became producing and performing in social media content, Zoom comedy shows, podcasts, cartoons, sketches, and more. I learn how important it was to be a versatile performer. 

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