Rising Star Leonard Robinson of HBO’s ‘Insecure’ on the Five Things You Need To Shine In The Entertainment Industry
It’s really okay to do your own thing: The entertainment industry rewards authenticity but oddly seems to encourage everyone to conform to certain standards. For example, “You have to be on Twitter if you’re a standup or want to write. People get jobs that way.” That may be true for a few people, but more people got jobs from being funny and great writers than being good at social media. Just do what rings true for you and know that it will be okay.
As a part of our series about pop culture’s rising stars, I had the distinct pleasure of interviewing Leonard Robinson.
Leonard Robinson currently recurs on HBO’s Insecure and has also appeared in numerous films and television projects such as Life of Crime with Jennifer Aniston and John Hawkes, NCIS, NCIS: LA, Adam Ruins Everything, Young Sheldon and Alexa & Katie on Netflix. Additionally, Leonard has appeared in theaters nationwide including “The Exonerated” at The Culture Project (Off-Broadway), Williamstown Theatre Festival, New York Fringe Festival, and Studio Theatre in Washington, DC. After graduating from Howard University, Leonard studied and performed improv/sketch at Upright Citizens Brigade, IO West as well as in the CBS Diversity Sketch Comedy Showcase. Leonard is currently a Main Company member of The Groundlings Theatre in Los Angeles. As a stand-up comedian, Leonard has performed all across the U.S. and the UK.
Thank you so much for doing this with us! Can you tell us the story of how you grew up?
I was born in Ohio but grew up mostly in Danbury, CT with a short stint in Tokyo for about 3.5 years. A lot of people talk about being raised in front of the television, but I think I was more obsessed with TV and movies.
Can you share a story with us about what brought you to this specific career path?
One of my earliest memories is watching TV and wanting to be on it. I’m not sure how I knew that what I was seeing was not real, but I remember seeing a kid on Sesame Street and thinking that should be me. I think everything thing I’ve done in my career to this point is just setting up to guest star on Sesame Street.
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?
The funniest mistake is actually what led me to my first agent when I was living in New York. A friend told me in an audition that you need an agent if you want to get the “real auditions.” The “real auditions” were not the ones posted in the back of Backstage Magazine. So, I found a directory of agents and went to the first one listed that did not specifically state “visits by appointment only.” I was not aware that you can’t simply pop up at an agent’s office in the middle of the day and ask to be represented. At the time, I thought a talent agent worked like a temp agency or something. They were so blown away by my ignorance of the process and industry that they decided to represent me. They were my agent for three years in New York.
What are some of the most interesting or exciting projects you are working on now?
I am very excited about filming the upcoming and final season of Insecure on HBO. It has been such a wonderful journey recurring on that show and I can’t wait to see how it all ends and what that means for my character Taurean. The Groundlings also wrapped on the first live sketch show we produced via Zoom. That was my first directing experience and it really lit a fire in me. I hope to direct again very soon.
We are very interested in diversity in the entertainment industry. Can you share three reasons with our readers about why you think it’s important to have diversity represented in film and television? How can that potentially affect our culture?
I’m not an expert in the field of diversity and inclusion. However, I can tell you how it feels to see people of all colors represented in television and film. It feels great. It feels like I’m seen. It feels like I matter. I think it also humanizes people of color when you see them play roles they have not been traditionally assigned. I don’t think it’s impossible to suggest that increased diversity in television and film can stop the seeds of racism and oppression from ever taking place, especially when you are seeing more complex and fully developed characters.
What are your “5 things I wish someone told me when I first started” and why. Please share a story or example for each.
- Enjoy the ride: Don’t feel so much pressure to keep working all the time. Give yourself boundaries and take time for yourself. Celebrate your wins! Any and all wins. Big or small — you celebrate.
- Comparison is the thief of joy: When someone told me this, I immediately wrote it down. Especially in today’s social media-dominant world, it’s easy to compare yourself and think you’re not doing enough. Don’t be fooled by all the hype. Keep your head down and just do the work.
- Make a plan for yourself and stick to it: You need a game plan or direction in this business or you’ll just float around in the wind, so make the best plan for your career based on your goals, needs and talents. Once you put that together, get to work on it! Every so often you might get some new information that might better inform your plan. However, that doesn’t mean you drop everything and just start doing something new. Don’t forget about your original plan!
- Keep your day job or survival just a little bit longer than you want to: I think there is a self-imposed stigma with having a day job, survival job, side hustle or whatever you call it. However, there is a real stigma with being broke. So, if you have to, keep working until you get to a point where you can live comfortably doing what you want to do. Bonus points if your side hustle is working within the industry.
- It’s really okay to do your own thing: The entertainment industry rewards authenticity but oddly seems to encourage everyone to conform to certain standards. For example, “You have to be on Twitter if you’re a standup or want to write. People get jobs that way.” That may be true for a few people, but more people got jobs from being funny and great writers than being good at social media. Just do what rings true for you and know that it will be okay.
Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?
I think rest is a very misunderstood and underrated tool. There is much push and influence out there to always be doing something that you can really be hard on yourself when you have nothing to do. Of course, you can always be working on creating something yourself, but I don’t think there’s anything wrong with taking a break to recharge. Your break can be a few days or a few months. The problem with social media is that it is a tool for comparison and judgment. You see your peers creating or working and now you feel bad that you’re not. This makes it harder for you to relax and recharge when you’ve just finished a project. I believe that is the cycle that leads to burnout.
You are a person of enormous 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? You never know what your idea can trigger. :-)
Wow, these are some DEEP questions. I think the movement would be about encouraging people to truly pursue their passions and what brings them joy in life as opposed to what they think will make them rich.
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?
I have had so many. Early on, I recognized that finding mentors would really help bridge the education and experience gap I had entering the industry. However, I was never able to find a dedicated mentor. So, I made a practice of taking moments with people when I had the opportunity to work with them. I got great standup comedy lessons and advice from comedian Lewis Black. He more or less started my standup career. I learned a lot working with John Turturro on a mini-series and he was very helpful sensing it was my first time on a project of that scale. Finally, I took Joe Morton to lunch one day when I was in a play with him in New York. His career advice still drives how I make decisions to this day.
Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?
I auditioned for Insecure about 7 or more times for at least 3 different characters starting from the pilot, before I booked the role of Taurean in season 3. For me, this falls into the “stay positive and never give up” bucket of life quotes. So often we hear that in this industry, but it’s easy to get negative and want to give up or makeup stories on why something is never going to work out. I’ve found, in this business, if you just keep doing the work, and learn to love the process, things will work out.
Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might just see this, especially if we tag them. :-)
It would probably be Jordan Peele. I am such a fan. I’ve loved watching his growth and evolution and how he’s really made his own way.
How can our readers follow you online?
Follow me on Instagram @iamleonardrobinson
This was very meaningful, thank you so much! We wish you continued success!
About The Interviewer: Growing up in Canada, Edward Sylvan was an unlikely candidate to make a mark on the high-powered film industry based in Hollywood. But as CEO of Sycamore Entertainment Group Inc, (SEGI) Sylvan is among a select group of less than ten Black executives who have founded, own and control a publicly traded company. Now, deeply involved in the movie business, he is providing opportunities for people of color.
In 2020, he was appointed president of the Monaco International Film Festival, and was encouraged to take the festival in a new digital direction.
Raised in Toronto, he attended York University where he studied Economics and Political Science, then went to work in finance on Bay Street, (the city’s equivalent of Wall Street). After years of handling equities trading, film tax credits, options trading and mergers and acquisitions for the film, mining and technology industries, in 2008 he decided to reorient his career fully towards the entertainment business.
With the aim of helping Los Angeles filmmakers of color who were struggling to understand how to raise capital, Sylvan wanted to provide them with ways to finance their creative endeavors.
At Sycamore Entertainment he specializes in print and advertising financing, marketing, acquisition and worldwide distribution of quality feature-length motion pictures, and is concerned with acquiring, producing and promoting films about equality, diversity and other thought provoking subject matter which will also include nonviolent storytelling.
Also in 2020, Sylvan launched SEGI TV, a free OTT streaming network built on the pillars of equality, sustainability and community which is scheduled to reach 100 million U.S household televisions and 200 million mobile devices across Roku, Amazon Fire TV, Apple TV, Samsung Smart TV and others.
As Executive Producer he currently has several projects in production including The Trials of Eroy Brown, a story about the prison system and how it operated in Texas, based on the best-selling book, as well as a documentary called The Making of Roll Bounce, about the 2005 coming of age film which starred rapper Bow Wow and portrays roller skating culture in 1970’s Chicago.
He sits on the Board of Directors of Uplay Canada, (United Public Leadership Academy for Youth), which prepares youth to be citizen leaders and provides opportunities for Canadian high school basketball players to advance to Division 1 schools as well as the NBA.
A former competitive go kart racer with Checkered Flag Racing Ltd, he also enjoys traveling to exotic locales. Sylvan resides in Vancouver and has two adult daughters.
Sylvan has been featured in Forbes, the Wall Street Journal, the New York Times and has been seen on Fox Business News, CBS and NBC. Sycamore Entertainment Group Inc is headquartered in Seattle, with offices in Los Angeles and Vancouver.
