Neil Rubenstein: Five Things I Wish Someone Told Me When I First Became A Professional Comedian

There’s No Book. — No rule book. No guide book. But that information can be crippling and stifling or that information can be empowering and freeing. Do with it what you choose. But you can get here a million different ways. And no one knows how or why.

I had the distinct pleasure of interviewing Neil Rubenstein.

Neil Rubenstein is a burly, tattooed guy who plays against type; kind, cerebral, but still casually mentions past illegal activities (running a poker room, owning a brothel, etc.) the way one might reference a Renaissance Lit course you took in college. Find out more about him or when he’ll be on tour in your neck of the woods at NeilRubenstein.com or on Instagram @NeilRubenstein

Thank you so much for doing this with us! Our readers would love to get to know you a bit better. Can you tell us the story of how you grew up?

I never had a chance at normalcy. My siblings are all so much older than me that I’ve always assumed one of them was my real parent. It just felt growing up that my parents wanted grandkids so badly, they just pretended I was one. Just smothering me when they were in grandparent mode and then completely neglectful when they grew tired of it.

My Father taught me all about scamming stores with return schemes and switching price tags. He had me running football parlay slips in my HS for him. My Mother gave me Munchausen by Proxy. Convincing me I was allergic to everything. Turns out I wasn’t.

Early on I discovered that I enjoyed spending the bulk of my life on the road and have been doing that most of my adult life.

Can you share a story with us about what brought you to this specific career path as a comedian?

I was on a show called Casino Cinema on SpikeTV for like 4 years. Artie Lange was a returning guest. And one afternoon he asked me about my goals and how I liked working on TV. I’ll never forget, he said, “shit ends, kid.”

And suggested I give stand up comedy a shot.

Turns out I’m about the only person in the world to take life advice from Artie Lange.

Can you tell us the most interesting story that happened to you since you began your career?

I don’t know about “MOST,” but it has been wild. A funny one, is right after Louis getting canceled, I went to see my buddy, Sean Donnely, at the Cellar in NYC. And I’m very face dumb, not to mention how terrible my eyesight is too begin with.

From the front of the Olive Tree, Louis & Sean don’t look that dissimilar to me. So I walk in and bee line to Louis. As I get closer I can see panic in his face. I’m just the large, angry looking, tattooed guy, barreling through a restaurant toward him. He has no idea who I am, and I’m looking at him, like, “Sean, don’t you remember me, your good buddy, Neil?”

Maybe it isn’t that funny. I thought it was funny. He was very nice about it.

It has been said that our mistakes can be our greatest teachers. Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I had a pretty regretful start / stop to my career. I just didn’t give it the love and attention it deserved and took some huge losses early on. Until I learned what it was I needed to do to get this right.

I honestly can’t recall a specific thing at the moment, but if I could, the more valuable lesson here, would just be to go out and mess it up yourself. Those lessons are better learned first hand.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

Too many to list. I was at the lowest point in my life after the pandemic hit. I got laid up for 14 weeks with a broken ankle. My wife left me. I had to file bankruptcy. I ended up moving halfway across the country. I fell into a massive pit, mentally. And tons of folks rallied behind me with places to stay and feel loved. And a few folks made sizable donations to make sure I could afford to get back on my feet.

There’s about 12 to 15 people out there that absolutely know how important a role they played in keeping me on this plane of existence.

You have been blessed with great success in a career path that can be challenging. Do you have any words of advice for others who may want to embark on this career path, but seem daunted by the prospect of failure?

It’s a cliche, but it really is about taking that first step. Every journey starts with a single step or some such bullshit.

I will say, if you have a plan B. If lawyering or public speaking or joining a toastmasters or a karaoke night will bring you the same kinda joy, GO DO THAT. This is a brutal addiction and will almost definitely destroy you before it fulfills you. This is the most humbling shit in the world. This is the Ayahuasca trip of career paths.

You have such impressive work. What are some of the most interesting or exciting projects you are working on now? Where do you see yourself heading from here?

No real plans. I’d really just like to keep touring. These last 6 weeks opening for the band Motion City Soundtrack have been surreal. If I could keep going out with friends’ bands in between runs at traditional comedy clubs, that’d be pretty ideal. Of course, I’d love if the industry noticed me a bit. Maybe land an HBO or Netflix credit here or there would be nice.

What do you do to get material to write your jokes? What is that creative process like?

Two major sources. One, I have opinions. Tons of ’em. So I make sure to voice them. How I feel about the things in our current social political climate. And two, traumatic experiences. I like to go back and unpack those and see what I can make funny from that.

Super. Here is our main question. What are your “Five Things I Wish Someone Told Me When I First Became A Professional Comedian” and why? Please share a story or example for each.

1 — There’s No Book.

No rule book. No guide book. But that information can be crippling and stifling or that information can be empowering and freeing. Do with it what you choose. But you can get here a million different ways. And no one knows how or why.

2 — Everyone’s Idea of Success Is Different.

I’m not as successful as I’d like to be. But I know plenty of folks that would take what I’ve got in a heartbeat. You will drive yourself absolutely insane if you compare your idea of success with someone else’s.

3 — The “Industry” Has No Idea What They Are Doing, Either.

You think you’re lost? You think you don’t know where to go from here or what to do next? Neither do they. Just keep getting better and more doors will open. Either swing open and you’ll have to kick them open, but if you keep getting better they will keep opening.

4 — There’s No Plan B. aka You Can’t Marry Both.

This has been explained differently to me over the years, but ultimately, as I touched on before, if ANYTHING else will make you happy. Do that other thing. This is brutal. It will consume you at all times. That’s just what it does. Only the best of the best get to keep anything else. And they probably lost it at one point, anyhow.

5 — Be Yourself.

Obviously this doesn’t apply to characters. But the reason most of us start is because someone in our personal life told us we were funny. Do your best to present that person every time you are on stage. The funny person people wanna be around.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

Nothing matters. It’s brutal to hear, but none of this matters. The person that loves you the most will eventually get over you. Nothing matters.

And once you accept it, you can start enjoying each moment individually. You can quit your job and run away from home. And tell your dumb jokes to strangers. And every night can be the best night of your life. And every night you can help a room full of strangers have the best night of their lives.

You are a person of huge influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be?

Honestly, I just want everyone to have a good time. Life is short & dumb & pointless. Let’s just enjoy each others company. But if I’m being pressed, I would like to see a world where more hot people slept with fat guys.

Is there a person in the world whom you would love to have lunch with, and why? Maybe we can tag them and see what happens!

Is it dumb to say Sarah Silverman? She’s my absolute favorite & my biggest influence. I’d love to be able to pick her brain for an hour over some matzah ball soup and a pastrami sandwich.

Are you on social media? How can our readers follow you online?

Yes, please. @NeilRubenstein

NeilRubenstein.com for all the other things. Shirts, Vinyl, additional links.

This was so informative, thank you so much! We wish you continued success!