Isabella Charlton: Five Things I Wish Someone Told Me When I First Became A Professional Comedian

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Always be ready to get on stage at the drop of a hat. You never know what can happen. If another comic doesn’t show up, you might be in the right place at the right time to be put up. You always have to be ready to get on stage. Great training for this is the Kill Tony Podcast, because open mic comics put their name in a bucket, and it gets drawn live on air and they have to run up to the stage and perform.

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 Isabella Charlton.

Isabella Charlton is a London born, US & Hong Kong based, stand-up comic, screenwriter, actress, and performer. Currently she has developed a one-woman show that will be showcased at the Hollywood Fringe Festival in LA at the end of June 2024, and she will then move across the pond to perform her show at the Edinburgh Fringe Festival in Scotland in August 2024. Her show tells of a dark steamy affair between her father and the family’s nanny. From London to Hong Kong, this twist-turning and ironic show takes us through the highs and lows of adolescence and adult love life, unveiling family secrets, power plays and salacious surprises.

Isabella has had success performing all over the world and she was selected to be a part of famed Hollywood Laugh Factory’s Fresh Faces for 2018 & 2019. She has also performed in LA at The Comedy Store, The Hollywood Improv, Westside Comedy Theatre, and The Ice House (in Pasadena). In NYC she has performed at The Stand, Caroline’s, and New York Comedy Club. Internationally she has performed stand-up comedy, in fluent Chinese, Hong Kong, China, and NYC even performing cross talk in Chinese which is a type of Chinese comedy from the Qing Dynasty. Isabella has taken part in The Comedy Store’s ‘Roast Battle,’ which can be heard on the Roast Battle podcast, and she can be seen multiple times on the Kill Tony Podcast live from the Comedy Store. She has also performed at multiple festivals including Trial by Laughter in Indianapolis, She-Devil Festival in NY, Big Sky Comedy Festival in Montana, Seattle International Comedy Festival, Boston Women in Comedy Festival, Laughing Skull Festival in Atlanta, Perth Fringe and the New Zealand Fringe Festivals, and performs regularly on Redband’s Secret Show in Austin.

Isabella currently splits her time between the US and Hong Kong where she speaks fluent Mandarin Chinese. Born in London but raised in Hong Kong, she is also a New Zealand resident as well as an Indian overseas citizen because her father is mixed race Indian and UK and was born in India. Her parents are both lawyers and Isabella also has an undergraduate law degree from Oxford and a Masters of Law from London School of Economics. In addition to working as a barrister in London, she was also an on-air reporter for TVB News in Hong Kong and a bilingual actress in Chinese language movies, television, and theatre in Beijing.

Inspired by comics such as Wanda Sykes, Zach Galifianakis, Maria Bamford, and Tig Notaro, Isabella hopes to have her own television series based on her one-woman show and to continue to write films and books. She is involved in two charities set up by her mother: Asia Education Foundation Limited & Asia Environmental Foundation Limited.

You can follow Isabella here:

Instagram: @isabellacomedy

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 was born in London, but I grew up in Hong Kong. Not the typical expat kid, because despite being British, my mum sent us to a Chinese international school, where we studied Mandarin Chinese from the age of four. My siblings and I would wake up at the crack of dawn to study with a tutor for the weekly dictations of characters at school. And we spent many weekends over the border in Shenzhen horse riding, lighting fireworks and practicing our language skills. Or at the Aberdeen Marina Club, a kind of country club in Hong Kong, bowling, sliding down water slides or setting off on a junk trip. A junk is a Hong Kong style boat, but typically refers to most boats in Hong Kong now. I grew up in the shadow and aftermath of the handover of Hong Kong from the UK back to China. I thought it was very exciting as a kid because for us there were massive competing firework displays. And heck, I already spoke the language. At the age of eleven, I was sent to boarding school in the UK, and dealt with culture shock and cold wet dark winters, I had never expected. Manners were different, and the rules I’d learnt to operate in polite Hong Kong society were confusingly often no longer relevant. You’re not meant to turn down every refreshment offered to you, like in Hong Kong, and expect to still be presented with it. And the tea tasted much worse! Short terms and long holidays in Hong Kong meant I enjoyed the best of both worlds.

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

I moved to Beijing in my mid 20s, after working as a lawyer in London, and decided to try my hand at acting in TV and movies. I landed roles immediately due to my mandarin language skills,; however, I soon stumbled across a type of live performance in China called Crosstalk, an ancient form of comedy from the Ching Dynasty. There were a few foreigners trying it out, under the tutelage of a famous old crosstalk master. I immediately wanted to try it out. It’s semi-scripted and performed with two people on stage, who are always talking at cross purposes, and that is where most of the comedy is derived. One character thinks they are smart and the other is dumb, but the other is never really dumb. I realized quickly though that a foreigner performing this was never going to be much more than an oddity in China, so I decided, after testing out to a few jokes at expat open mic in English, to travel to Chicago and try Stand up comedy/ From there I went to San Francisco and then settled in LA.

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

The truth is the most interesting story has been all the people I’ve met doing stand up, especially at the beginning of my career during the open mic stage. The most interesting and diverse people, I might never have met in my narrow world, are drawn to try stand up. They often have something to say but haven’t quite found the medium to say it in yet; perhaps they’ll stay in stand up or it might just be something they are trying out. People who have experienced trauma are often drawn to stand up and art in general. I’ve known two comics who grew up in cults. People from all levels of society try stand up; it’s not uncommon for a few comedians on the scene to be living out of their cars. People from all different countries try stand up; in LA, I’ve worked with comedians from Bosnia, Yemen, Russia and China. Stand up is the great leveler because everyone is completely equal to each other in front of the audience; the only thing that can distinguish one another is getting the greater laugh.

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?

When I first started comedy, I fancied myself an alternative comedian. I spent four weeks studying at a clown school in Paris. This is a common trope for “would be” alternative comedians. If you’ve seen the TV show, Baskets, it was exactly like that. I’d also done a handful of stand up open mics, so I considered myself a fully fledged comedian, despite being unbelievably green. I persuaded a friend to get me some stage time at the prestigious Edinburgh Fringe Festival, which he dutifully did. I then showcased my alternative comedy act for the world, which consisted of handing out chocolate to the audience, doing a five minute stand up set, and then asking the astonished audience to give me my chocolate back. Most of the chocolate had already been eaten. And the audience sat there awkwardly as I restlessly pleaded with them and angrily demanded the chocolate back. I thought it was hilarious. No one else in the room did. I could see things souring, when I noticed my friend who had recommended me for the show, was watching horrified with his hands covering his face and only his eyes peeking out. I realized my mistake that day and I became more interested in capturing a mainstream audience than I thought.

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?

Making it in stand up is rarely about one big break with one person being solely responsible for helping you to get it — it’s lots of little breaks with many people helping you along the way. There are countless individuals that helped me out, gave me the next step up or just made me think I was on the right path. From the organizer of the Big Sky Festival in Montana, who saw me perform once in LA, and decided to give me a chance despite being the least experienced comic at the festival; to a top comedian, who was the guest when I performed on the Kill Tony podcast, and decided to recommend me to the New York comedy clubs; to a recent SNL star, who told me I was very funny when I went on before her at a club in LA. I’m grateful for the help from all of these people (and countless others!).

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 genuinely believe anyone can be funny, and it’s about putting in endless hours and being sensitive to your audience. It is a very fun job for someone that never wants to fully grow up. But often you get paid in make believe money for the first few years, so you have to be very self-motivated. It’s helpful to be more process than outcome driven. My advice would be to decide if you really love comedy and are willing to sacrifice everything for a chance at doing it. If you can find the most washed up comic who’s put their whole life into it and never made real money but still gets a kick out of being on stage, and look at them, and still think, “I’d love to have that,” then this is the career for you!

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 one woman Fringe Festival Show, called, My Dad F*cked the Nanny’. It’s a risqué title, but I can assure you, it’s a comedy. I’ve performed some version of it all over the world, at the Fringe festivals in Australia and New Zealand, and most recently at the Hollywood Fringe. And I’m taking it to the Edinburgh Fringe Festival for a full run this August, playing at the Gilded Balloon. The show is the true story of when my dad ran off with the nanny in London, and my mum packed her bags and how I ended up living in Hong Kong. But it’s also my story and about how my parents’ reactions to these events influenced me and how I ended up playing out my own version of their lives in adulthood.

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

I think I get a lot of jokes from day dreaming and letting my thoughts run wild, especially when I go for walks on my own. I also like trying to make my friends laugh and writing while on stage by riffing. There is a process to try to refine the joke, so anything unnecessary to the joke is cut out.

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. You will never be happy with where you are. As soon as you’ve achieved your goal in stand up, the next seemingly unachievable goal will suddenly loom before you and you’ll want that next thing. It will start off small, wanting to be booked on a show, you’ll get booked and entitlement will slowly creep in, and you’ll want to be booked on a bigger (and better!) show or festival. In 2019, I was lucky enough to do three festivals: Seattle Comedy Festival, Big Sky Comedy Festival and Laughing Skull Festival. My dream. But as soon as these festivals were over, the hunger for the next “big thing” returned… An unquenchable appetite, which will leave you, never truly satisfied.

2. Stay in touch with people and be active on social media. Either by posting or direct messaging, you need to be able to reach out to people. Your contact list is your guest list for shows. Your value as a live performance comedian commercially is how many seats you can fill. Kevin Hart was the original master of this, collecting emails when emails had just become a thing. You can bypass some of this by becoming a viral social media star and building fans. In order to build an in-person fan base, people need to see you perform, and to see you perform they need to have heard about your show. This may be tough for many comedians. Being a funny comedian doesn’t always go hand in hand with being able to market yourself. But just do it. This goes for comedians just starting out too, when you might even need to bring people to your shows to get stage time.

3. Make friends with other comedians. Be likeable. This is a hard one, because a good number of comedians have a misanthropic style to their comedy that bleeds into their life. They like who they like, and it’s not everyone. But if you’re going to treat comedy like a profession, you have to be aware that like every office there are politics. Comedians can often get booked, not based solely on how funny they are, but how likeable they are. This goes particularly for comedians on the road, they want to book an opener that they like sitting next to in the car or on the plane. Someone who can match their vibe and is chill, whatever their version of chill is. I know a comedian who buys all the other comedians drinks all the time; you might think this is a waste of money, but she gets booked a lot. Don’t become an alcoholic but be nice and friendly to everyone, it might pay off.

4. Always be ready to get on stage at the drop of a hat. You never know what can happen. If another comic doesn’t show up, you might be in the right place at the right time to be put up. You always have to be ready to get on stage. Great training for this is the Kill Tony Podcast, because open mic comics put their name in a bucket, and it gets drawn live on air and they have to run up to the stage and perform.

5. Find a partner who loves stand up. Don’t be with someone who loves you and just tolerates what you’re doing. That will wear very thin very quickly. An ideal partner is someone who would secretly love to do what you’re doing but doesn’t have the courage for performing or the stomach for the artistic lifestyle. But in some way, they get it. And they admire you for doing it. It’s not easy to find this person but they are out there. I’ve noticed the partners of successful comedians often fall into a few categories; chefs seem to be one. Both Amy Schumer and Iliza Shlesinger married chefs, who probably have an understanding about working unsociable hours. Other comedians is another. There are a few notable comedian couples. Natasha Leggero and Moshe Kasher. Elenor Kerrigan and Andrew Dice Clay. Rosebud Baker and Andy Haynes. They probably all get each other. And there are a lot of miserable single comedians. Just wait for someone to come along that gets it.

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

Sure, as she surreptitiously googles life lesson quotes… I think my mum actually gave me two quotes that helped. They’re both about not hiding in a box when you feel humiliated, and not giving up. When I’d tell her a group of people actively disliked me and were talking about me she’d always say, ‘it’s better to be talked about, than not talked about’. And if I ever felt like I really didn’t want to go to something she’d quote a comedian who said, ‘showing up is 80% of success’.

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?

I would pick animals and make everyone worship dogs and cats as sacred deities, but the question refers specially to helping people. I’d probably try to encourage people to stop trying to skip out on jury duty. It literally might be the difference between you going to prison falsely accused, if no one intelligent has showed up for jury service or is listening, and being acquitted. But that might be the ex-lawyer in me.

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!

David Letterman would be fun! In Hong Kong, I regularly watched his show as a kid at midnight and would be so shocked when he did crazy things like throw TVs off buildings.

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

You can find me on Instagram at @isabellaiscomedy

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


Isabella Charlton: Five Things I Wish Someone Told Me When I First Became A Professional Comedian was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.