Allan Sidley of Sidley Standup: Five Things I Wish Someone Told Me When I First Became A…

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Allan Sidley of Sidley Standup: Five Things I Wish Someone Told Me When I First Became A Professional Comedian

Being the funniest in the room doesn’t equate success. There’s so much marketing, networking, and luck involved. I really thought if I was undeniably good at my craft, better gigs would appear in my lap. It helps, but I sometimes regret not doing some heavier networking early on.

As a part of our series called “Five Things I Wish Someone Told Me When I First Became A Professional Comedian”, I had the distinct pleasure of interviewing Allan Sidley

A Baltimore based comedian, author, actor, hip hop improviser, and producer, Allan is a little all over the place, literally. He has performed in festivals, clubs, theaters, and colleges across the country, most notably opening for Keegan-Michael Key in Detroit. (It was a lot like Baltimore.) Even though Allan lost his dad when he was 10 months old, he mastered the “dad joke” and wrote an entire book of them. Featuring 187 pages of original jokes, Daddy Issues: A Fatherless Comedian’s Original Jokes was a #1 new release on Amazon. After not being on stage at all during the pandemic, Allan lost his mind and recorded an hour-long comedy special on Father’s Day 2021. He was seen on Fox 5 DC talking about his book, comedy, and special taping. Daddy Issues: The Stand-up Special is on YouTube.

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 grew up in an affluent area without the affluence. Raised by a single mom, she enrolled me in sports at a young age where I learned I was athletic and that I hated losing. In my household I felt a combination of love, insecurity, and anger- everybody I knew had two parents and more money. The persistent chip on my shoulder which helped me push myself to be better and compete at a higher level. Although my achy joints signal that those days are behind me, the underlying drive to be great and make an impact remains.

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

I’ve always loved comedy! Mel Brooks and Monty Python movies, Seinfeld, lots of standup, the Chapelle show, and South Park. I loved the different styles of humor and thought I could do something like that someday. I was a generally reserved kid, but I had the laughs from my various zingers to prove it. Stand-up felt like something I was going to do eventually. Fast forward to first job out of college, a few months in and I’m like, “this is it?” I was miserable! I needed a creative outlet, so I found myself taking a few improv classes and never looked back.

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

I once wrote a letter of recommendation for a local comedian applying to film school. I didn’t think we were that close, but I really got into it. She was a hard worker, funny comedian, and had the opportunity to fill a unique void with her point of view. She got in.

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 consider myself a very traditional comedian in the sense I’m a set-up, punchline comic. However, I saw an opportunity for performance art and got excited at trying something different. I was hosting a Halloween comedy show and dressed up as Pikachu, the main character from Pokémon. Now in Pokémon, Pikachu can only talk in “Pikaspeak.” For 10 minutes I pretended I was talking about real issues but uttering “Pika, Pika Pikachu pika, pee, etc.” with varying levels of intensity. I did crowd work with it, one time I looked at my notes and acted like I had some great revelation, then kept speaking gibberish. The audience was packed with people recording me with their phones but not laughter. In retrospect I should’ve splurged on the $200+ costume that would have covered my entire body and face. Although I was committed to the bit, I was still a bearded guy wearing a Pikachu hat with a yellow shirt and pants.

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?

My wife is always honest with me, even if she’s not always 100% right on how an audience is going to react to a joke! She was my editor for “Daddy Issues: A Fatherless Comedian’s Original Jokes.” She did an excellent job helping me refine that project to a quality that we’re both proud of. I bug her all the time about comedy, and she puts up with it, that makes her a saint.

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?

I credit my friends with getting my start. They encouraged me to try stand-up, and one of my best friends enrolled into an improv class with me. Without that little kick I’m not sure if I would have ever gotten started so let this be your kick. My advice is to rip off the bandaid. Then you can learn if it’s something you want to do more. Starting out is fun because you have no expectations, and everything is new. I wish I could retrain my brain to think I’m new, I’m stuck with all these annoying expectations after doing it for 10+ years.

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?

I’m currently working on my next stand-up special: New Dad, Dead Dad. Eye catching, right? In my last special I covered so many topics, in this one I’m going to be laser-focused on the biggest life events that shaped me, losing my dad at 10 months old, and having a new baby girl. I really think if I do it right, it could turn some heads.

I’m a local impact leader for the Maryland branch of the American Heart Association. In addition to raising money for a cause that’s important to me I’m hosting a comedy benefit series of five shows in Maryland and DC!

I’m always putting out silly sketches/stand-up clips on TikTok, some of which have gone viral.

The hope is at some point in the future somebody will look at my portfolio of publishing a book, having hours of material and stand-up clips online, and realize with a little bit of help I could go so far.

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

My mind is always wandering either reflecting on life or what’s going on around me. Whether it’s family, religion, work, dating, a lot of my jokes come to me that way. Anything to put me in a better headspace- coffee, exercise, hanging with friends that make me feel funny.

That being said, for this new special I’ve had a more “traditional” approach as I’ve spent some serious time revisiting some of the challenging parts of my childhood, even mining my mom for some material. Since it’s for comedy I’ve been focusing on some of my harder experiences, but the resulting jokes come from a place of brutal honesty, and I like 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?

  1. Comedy isn’t for the faint of heart, you need some thick skin. Whether it’s a bad night, you get heckled, or a comic says something nasty to you, you can’t let it affect you. I was so sensitive when I first started that if I didn’t get a laugh on every single joke, I thought I bombed, which was crazy since everything was so new. It’s still a journey for me but I try to focus on the feedback from audience as a piece of information and not an overall assessment. A particular joke works or it doesn’t, as opposed to I’m the best comedian or the worst one.
  2. Be confident in yourself regardless of what’s going on in the room. Sometimes I’ll be performing at a spot and a comedian drastically different from me will be doing surprisingly well. You almost feel that pull of “maybe I should be more like them, or at the very least talk about similar topics tonight.” When those thoughts come I’ve learned to quiet them and remember, just because they like X doesn’t mean they won’t like Y. So, I should do what I came to do. Looking back on it, I had some great jokes in my earlier days that I just wasn’t confident enough to execute properly. Funny how that works.
  3. Never do anything for free with the hope of getting paid work later. Either accept it as getting experience or get paid your worth. (This applies to corporate comedy mostly because if someone asked me to open Madison Square Garden for Chris Rock, but only for free I would still do it.) Back In 2013 I quit my job to pursue comedy full-time. Making a living as not-famous stand-up comedian living in Northern Virginia was a challenge. One of the ways I generated income is by hosting corporate shows and workshops. A previous employer of mine caught wind and reached out. They wanted me to do one pro bono with the possibility of doing something paid months later. The session was great, I combined fun improv exercises in a way to help build rapport, morale, and get people thinking more creatively. The session was a hit, but when I followed up months later for a paid opportunity, they acted confused. And I thought it was bad enough I got underpaid when I worked there!
  4. Being the funniest in the room doesn’t equate success. There’s so much marketing, networking, and luck involved. I really thought if I was undeniably good at my craft, better gigs would appear in my lap. It helps, but I sometimes regret not doing some heavier networking early on.
  5. Take breaks! It’s easy to get stuck in the grind. Just because you have peers performing 5/6/7 nights a week making themselves miserable doesn’t mean you have to. It’s easy to get stuck in the “I’m a miserable comedian” lifestyle, but it’s a choice. Enjoy your life!

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

Back when I was playing peewee football Chumbawumbas’s hit song “Tubthumper” came out and rocked the nation. Although not an appropriate song for children, the lyrics, “I get knocked down, but I get up again, you’re never going to keep me down!” was both our football team anthem and something I always go back to when I face a disappointment in my career. Whether it’s a social media post not getting attention, bookers and clubs ignoring me, or an audience not responding how I think they should. You’re never going to keep me down. The only way I lose is if I stop.

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?

Support local artists! Besides that, I’m really committed to my cause for the American Heart Association, if you’re able to donate or help, great! If not, please make sure you learn CPR and go see a doctor to check in on your health on a regular basis. We can easily save so many lives!

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!

I’ll give you three hilarious minds! Larry David, Anthony Jeselnik, and Mel Brooks.

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

@SidleyStandup on IG

@AllanSidley on TikTok

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

Allan Sidley of Sidley Standup: Five Things I Wish Someone Told Me When I First Became A… was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.