TIP 043 | The Daily Show

TIP 043 | The Daily Show

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Entertainment is a harrowing industry full of ups and downs, but how does someone go from Law to being on one of the most respected shows in comedy. Hear the incredible story of The Daily Show’s Ronnie Chieng.


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How comedian Ronnie Chieng worked his way to one of the most respected jobs in comedy.

From The Comedy Cellar to The Daily Show

Many of you may have figured out we have with us the legendary Ronny Chieng. Ronny, thanks so much for coming on the show.

Thanks for having me.

For the people who don’t know who you are, why don’t you tell us about yourself?

I’m a stand-up comic actor, writer, correspondent on The Daily Show. I’m Malaysian, ethnically Chinese. I grew up in Singapore and I went to law school in Australia. I’ve been in America for the last two years working on The Daily Show.

Americans probably weren’t that familiar with your work. All of a sudden you’re one of the most prominent comedians on television where on about a weekly basis, you’re on The Daily Show doing stories and original pieces. That’s incredible. What happened there?

I was doing okay in Australia, comedy-wise. I was building my fan base in Australia and I got invited to perform at the Just for Laughs Comedy Festival in Montreal for stand-up comics. It’s a huge deal for us. It’s like the Comedy Olympics, being asked to come and perform there. It’s legendary for the American comics who have been chosen to perform there in years past. I got invited to perform there. I did Eddie Izzard Gala. Trevor Noah happened to be on that show. I did about ten minutes. It went really well. Trevor saw my set and he said very complimentary things about it. We talked for about 30 seconds and that was it. We never exchanged numbers. We didn’t speak again for two years. I was very surprised when he took over the show, I got an email asking me to audition for The Daily Show.

I suspected it was him because the email didn’t come from him. It came from the production company. How else would they have known about me? I auditioned for it and over the course of a couple months, I got hired to be on the show. It was a real dream come true. I was intending to move to America to try to do comedy here and I had no idea how I was going to do it. I was just going to come in and wing it with no illusions. In America it’s very hard to transfer laterally in show business. I can’t speak to business or anything else, but show business, America doesn’t really care about what you did outside of America, even if you’re talk about The Office. The Office was remade in America, for example. It’s very hard to transfer laterally in show business from whatever profile you had in your home country to America unless you’ve done something in America.

There are celebrities in Indian culture that are so massive.

Shah Rukh Khan, literally the most famous actor in the world. He can’t get through customs, can’t get through immigration, gets held up at immigration for questioning.“Who are you? What are you doing here?”Yet he still tries to come to America.

Priyanka Chopra might be the only Indian actress that really made the jump. I can’t imagine how difficult it is. It’s pretty incredible because The Daily Show is this mantle where so many great comedians have come through and really defined their career.

It’s a huge honor to be asked to be a correspondent. I’m a big history fan and I’m also a big comedy nerd. The comedy history of The Daily Show is incredible.

In your time there, are there any stories that you just absolutely loved filing?

I’ve been pretty lucky. Everything I’ve done there, I’ve been really happy with.

Did you do a story about gay marriage?

It’s about how this elderly male gay couple back in the day they couldn’t get legally married, so instead one of them adopted the other.

It was so that they could have inheritance. If somebody died, then the other person would get their procured property. It was because all the complaints where, “If we allow gay marriage, then what’s to stop a father and son from getting married?” and you literally tracked down the only example of that ever happening.

No one made a big deal about it. They’ve already adopted each other. It was a legal loophole to, as you said, for inheritance purposes. I tracked them down and was just ironically disgusted of a father marrying his son. The thing was that the Supreme Court in America allows gay marriage now. Every city in America essentially, for practical purposes, allows gay marriage. They were trying to undo the adoption and marry each other, but they couldn’t marry each other because the father can’t legally marry his son. Now they have a bigger problem. They couldn’t get married because one was a father and one was the son legally. They’re trying to undo the adoption. They were very elderly, very sweet couple in Pennsylvania. They have been together a long time. It was exactly an elderly couple. I love that you know that one. That’s a bit of a deep cut.

It was so clever that you were able to track down this one obscure case that completely disproved what people were concerned about.

It was a team effort so everyone at the show produced that.

It takes thousands of man hours to produce. I’ve been watching The Marvelous Mrs. Maisel, and I am struck by how brutal it is to be a comedian.

TIP 043 | The Daily Show

The Daily Show: Public speaking is number one fear over heights or whatever it is. People would rather die than talk in public.

I just did something with some wrestlers, American Professional Wrestling, and they were hinting like, “I don’t know how you go on stage and do jokes.” I’m like, “You are literally bleeding from the mouth right now because I will kick you in the face, and you are telling me about telling jokes onstage.”Public speaking is number one fear over heights or whatever it is. People would rather die than talk in public. My point is everything is tough. Everyone’s job is tough. Stand-up is alchemy. You’re trying to make gold out of nothing, literally nothing. You’re just trying to make people laugh. You’re trying to make a room full of people expecting to laugh. That’s one of the hardest things to do. I won’t put you on a pedestal. I don’t think it’s the most dangerous thing. You keep asking me about bombing and not doing well. It sucks but if you do enough, if you bombed enough, if you do stand-up comedy enough, what happens is you can start to recognize the energy signatures of that emotion and it becomes a familiar feeling. You can deal with it better in the sense of you know what the joke is supposed to feel like when it’s going well. You know what it feels like when it’s not going well. You felt you’re not going well enough where you’re like, “This sucks, but I know this feeling” and so it’s less bewildering because it’s almost like a familiar, “I know how this feeling goes,” and then hopefully you can move past it.

When I started out, it was tough. It was brutal. You would really beat up on yourself if a joke didn’t work. After awhile, you get enough experience. You get more wins than losses. You know that you know that you don’t suck, you know that you can make people laugh if you need to, but you’re bombing because you’re trying new stuff, which is important. That’s how you get better jokes. That’s how you have new material. It becomes a professional thing like, “I bombed here, but that was a professional bomb.”

I’ve met a lot of funny people over the course of my life, but I wouldn’t recommend that most of them become comedians. How do you know? I can crack a joke and make people laugh.

That’s a very astute observation. There is a difference between street jokes, making your friends laugh, and doing stand-up comedy. I’m not saying this to put stand-up comedy on a pedestal. It’s one of the most accessible art forms. You can just jump on an open mic and do it. You don’t even need to hopefully bring any equipment. You can just bring yourself. It’s very accessible in terms of barriers to entry. Unlike ice hockey, you have to buy all this gear and all that. Stand-up doesn’t, for example. Not to put stand up on a pedestal, but there is definitely a difference between funny guy amongst your friends and doing stand-up. You don’t have to take my word for it, you can just go up on stage and try it. That’s not a threat. I’m not saying you personally. Anyone who believes they’re the funny guy in a room, go on stage and try it. Who knows? You might be able to actually tailor your talents to the stage and maybe you won’t. You will definitely find that it’s a different context, a different medium. They’re almost only tangentially related in terms of making conversations.

One of the interesting things about comedy is whereas in a lot of other performing arts, you can’t phone it in. If you’re a magician, you could be a really crappy magician and still do a trick. You can’t be a crappy comedian, like a really bad one, because people either laugh or they don’t. You’re either funny or you’re not.

I don’t think you can be crappy in any performing art.

You could be a really bad magician and people will still be impressed because the trick is a technical thing.

Maybe there’s something to that, but I would say just like anything, you can’t be bad at what you do. Just like anything, in stand up there’s nowhere to hide. Unless you play a musical instrument, you can play that. There’s no partner on stage unless you’re doing a double act. It’s all on you and there are no other distractions on stage. You’re very exposed. It takes a while to get the hang of it.

Do you have an affinity to brick walls?

Yeah. They knew the aesthetic. I actually talk about it sometimes when I’m in front of a brick wall. I used to watch Seinfeld. When I was a kid, I’d be like, “Maybe someday I can do that.” I remember telling my mom, “Maybe someday I can go on stage and tell jokes.” She was like, “Whatever.” I didn’t do it for twenty years. In New York, when I go on stage at The Cellar, which is the premier brick wall of comedy, I remember I got on stage and I’m like, “I made it to the brick wall. I used to watch Seinfeld. I used to see that brick wall and be like, ‘Maybe someday I can do comedy in front of the brick wall and I made it to the brick wall.’”It’s an iconic New York stand-up brick wall. For better or for worse, all over the world, stand-up comics put New York on a pedestal for stand-up comedy. Moving here, I can confirm that it’s definitely one of the makers of stand-up because there are so many gigs you can do a night. You can do three or four gigs a night every single night if you wanted to. I don’t know any other city where you can do that. London, you can’t do that. That’s like the second comedy capital of the Western world. LA, you can’t do that, and there’s Hollywood. There’s no other city where you can do this many gigs and have this kind of audience. The amount of comics here pushes everyone a little bit to be a bit better. You can’t rest on your laurels because there’s so many comics that you have to be constantly working on what you do. There is something here, the energy of the city that lends itself very well to stand-up and that brick wall.

What’s something completely unexpected about reaching this level of success?

TIP 043 | The Daily Show

The Daily Show: Nothing is ever the end. You don’t reach this thing and then you go, ” I’m done.”

I hesitate to talk about that because I don’t feel like I’ve reached any dizzying heights of success. I’ve had some thoughts about how nothing is ever the end. You don’t reach this thing and then you go, ” I’m done.”Whatever your goal was, for example, “I want to sell a theater.” You sold it and everything’s just a step forward. What I’m saying is like you can’t have the attitude of “once I do this, once I achieved this, everyone knows who I am and I’ve made it and everyone owes me anything I want now” because that’s just not true. I guess it’s “don’t believe your own PR” is really the message there, which I’ve always suspected since I started out. First of all, we don’t live in monoculture. We have all these different niche cultures. I keep saying don’t put stand-up on a pedestal and what I mean is that I understand that it’s a sub-group of main cultures. I don’t expect everyone to know every single stand-up or even the famous working stand-ups.

If you’re doing this for fame and money, you’re going to be very disappointed. You’ll never have enough money and you’ll never have enough fame. I know that’s easy for me to say because I’m making some money doing what I love. It’s easy for me to say, “If you’re doing this for money, that’s not going to fulfill you,” because you’re talking to someone who’s starting out and struggling and who’s like, “All I want to do is make somebody from comedy.” My broader point is that if you’re just doing stand-up to get famous and to make money, you will never be famous enough. We don’t live in this monoculture where we have the same cultural heroes. Everyone finds their niche of subculture to view things in. You might now have crossed over. You might be the most famous stand-up but that doesn’t mean people who watch television know who you are. It doesn’t mean people who watch movies know who you are. It doesn’t mean people who listen to music know who you are. It’s very unfulfilling. If you’re doing it because you’re actually genuinely love going on stage and making people laugh, if you could hold on to that, you will be able to find happiness doing it. It’s tough to do it. It’s tough to motivate yourself to go out every night and jump on stage sometimes, especially if you have a day job. I’m working at The Daily Show in the day and then at night I go to stand-up. Stand-up will be actually the easiest thing to stop doing. The only reason I still do it is because I love doing it and I’m in New York City. It’s always been a dream of mine to do that, and the shows here are good. If you don’t love doing stand-up itself then it’s going to be tough to keep doing it.

That’s great advice because the fact is that there’s always more to be gotten and people are always going to want more no matter what level they’re at. Research shows that what’s probably more important is being engaged in what you do and feeling like you’re an active participant that’s creating your experience of life.

I love how you took something that took me a couple years to suspect. You’ve quantified it in a very scientific, clinical psychology way. I agree with you. We just said the same thing. I’ll remember how you phrased it.

I had the pleasure of hosting Roy Wood, Jr., one of your colleagues. He’s the greatest. He shared a story that was complete insanity about how he got the start to his radio career. He essentially shared that he went to some comedy club telling them that he was the new radio host for the radio station. He told the radio station that he just booked a big stand-up gig opening for some act at the comedy club and that they should come and check him out for that, and if they liked him, they should hire him for the show. He had to keep the radio station people away from the managers of the comedy club that night so that he could do his set and not get in trouble, and then he got hired for the radio show.

He is honestly the best. That’s just an example of him trying to hustle and make opportunities for himself. When I first moved to America, he joined the show as well. We were both correspondents at the same time. He’s the most genuine generous guy you’ll meet in stand up. He’s very generous with his time. He never has a chip on his shoulder, answers you very sincerely, and will try to help you out in any of your problems. He was my guide to America and black America. He’ll give me the low down on everything in American comedy because he’s seen and met almost everyone. He really worked super hard. He’s been to every single state. He does comedy. He would drive five hours to do ten minutes when he started out. He’s a crazy man.

As far as your career, do you have any crazy stunts or bets that you took that really paid off or maybe even failed miserably?

I never had a story like that. I definitely have my breaks like the last thing that I told you about. Honestly my approach to stand-up, which I think for better or for worse there’s upsides and downsides to this, was I always try to let my act speak for itself. I wasn’t heavy on the self-promotion. That’s how I built it in Australia. My philosophy was to have word of mouth but also to decrease supply. The only way you could see me was to come watch my show. Buy a ticket and come watch my live show. I wasn’t on TV, not that I had a choice. It’s not like they were knocking down the doors to try to get me on television. On social media, I’m very choosy of what I post on social media and that approach has gotten me so far. I’m starting to wonder if I need to tweak that algorithm a bit and put myself out there a little bit more. I feel like in America, you have to constantly be pitching yourself, selling yourself. Whereas in Australia, my philosophy was I didn’t want to tell people that they should come watch me. I never wanted to sell people on it. I always just was like, “I’m doing a show here. I’m lucky that there’s a lot of buzz about me. Come see what it is. If you don’t want to come, that’s fine too.”That’s how I built it, almost reverse psychology. I never had any stories of begging people to come watch me.

You’d suggested that if people are curious about comedy, they can just get on an open mic night. Is there any other advice that you have for young comics or people who are thinking about it?


There’s no substitute for stage time. You got to spend some time prepping your first set or every set you do every time you write a new material. The hesitation doesn’t really add anything. You’ll learn way more by just going on stage and even bombing. You’ll learn way more from that than just trying to figure out the theory before going on stage. Also, self-awareness is very important in comedy. It’s very hard for people, even your closest friends, to tell you this didn’t work or why this didn’t work. You need to be aware yourself that something isn’t working and then change it. You need to be aware. Self-awareness is crucial. The other insight, which goes to my trying not to put stand-up on a pedestal here, there’s also other ways to do comedy.

TIP 043 | The Daily Show

The Daily Show: If you’re doing this for fame and money, you’re going to be very disappointed. You’ll never have enough money and you’ll never have enough fame.

Stand-up is one form. You could do improv, you could do funny videos, you could do funny sketches, you could write movies or funny screenplays. There’s different ways to express yourself comedically. Stand-up is very challenging. You can learn so much from doing it that can help you in these other areas as well. It’s one of the purest forms of it because you have to go on stage and make people laugh. If you can do that, you can do anything. That being said, I also know plenty of very funny people who don’t do stand-up. Improv is a very difficult thing to do as well. If you become a great improviser, that’s very useful as well. That’s something I didn’t know until I moved to America. I saw these improv guys do it at a very high level. In fact, most of the writers at The Daily Show come from improv. They’re so quick to come up with jokes and their improv muscle is so strong.

Jordan Klepper is a legend at improv. He’s this Midwestern guy, down to earth and very generous with his time and his advice and very friendly. You don’t know that this guy, Jordan Klepper, everyone in improv has either been taught by him or has performed in a show with him. He is the Kevin Bacon of improv and for good reason, he is unbelievable on improv. That’s another way you can express yourself. Just to give you some warning, for some reason, improv and stand-up is like vampires and werewolves. For some reason, they never cross. I don’t know what it is. It’s like if you practice that muscle, you can’t do that muscle. Very few people have that ability to crossover.

One is all about the immediacy and the other is about the refinement.

It’s weird that you would expect there to be more crossover between the skill sets. There is some, but for some reason, they go into different worlds, they have different political hierarchies, and all that.

Do you have a story or something you’d love to share from work?

I was doing this Jesse Watters piece on the racism in Chinatown. I remember going down to Chinatown to film people’s reactions to this piece that was broadcasted on Fox News, making fun of Chinese people. I expected apathy because back home in Malaysia and Singapore people can be very apathetic when it comes to talking to television cameras and about politics. I didn’t know if we could get enough people to give their opinions on what happened on this TV segment, which I’m not even sure the people in Chinatown watched even though it was going viral globally, but that’s the internet. I went down to Chinatown and I was surprised. As soon as I got out of the car, people lining up, they were like, “Are you here to talk about that thing that happened yesterday? Okay. Come over here.” People lined up around the block to shit on this piece. I was really heartened by the passion that people had speaking for their community. It wasn’t just Asian people talking to me. There were white people and the white people were like, “We live here in Chinatown and this makes us look bad, this whole piece.”

Just to give the listeners some background, what was the story?

It was a Fox News segment where they sent this correspondent down to Chinatown to ask Chinese people about their views on the election. Essentially, it was just making fun of old Chinese people who couldn’t speak English and asking them political questions in English and then trying to get their answers, and obviously they don’t know what was going on. Our counterargument was that Chinese people, Asian-Americans have sophisticated political opinions as well in English if you ask the right people, but also even in Chinese. I went down to China town to ask them political questions in English and in Chinese, and get their thoughts on that. That was the angle we took.

TIP 043 | The Daily Show

The Daily Show: You have to go on stage and make people laugh. If you can do that, it feels like you can do anything.

One of the things that I respect is that because of the nature of The Daily Show, the fact that it’s satirical, you can get away with making statements and saying things that the traditional media just can’t attack. You guys have done a really great job of honoring the mantle that has been created over the years. I have to applaud you.

Thank you so much.

Ronny, thank you so much for coming on the show. I really appreciate it. I’m a huge fan of the work that you do and I respect it a ton. Listeners, if you want to find Ronny, you can obviously see him at The Comedy Cellar quite often. Where else can they find out more about you?

Just go to my website. I put my shows there, RonnyChieng.com.

We have another anonymous interview and if you can figure out who it is, you can win an invitation to me here, The Salon by Influencers. Good luck.

About Ronny Chieng

TIP 043 | The Daily ShowStand up comic, Correspondent on The Daily Show, Actor on Crazy Rich Asians the Movie, Co-creator and star of TV comedy series Ronny Chieng: International Student

Anonymous Guest Interview

For the anonymous interview, we have an actual legend with us. Dean, thank you so much for joining us.

Thank you. It’s my pleasure.

Dean, let’s give the listeners some background on you so that they can try and figure out who you are. Where’d you grow up?

I grew up in Dallas, Texas.

Was there a certain teacher or incident that inspired you to go into the career you went?

I actually was planning to be a photographer. I worked my way through school as a photographer. I found photography to be magical. I had my own dark room when I was eight or nine years old. When I was twelve, I went to work for the best portrait photographer in Dallas. I worked as an apprenticeship with him for three years and then I opened up my own portrait studio then later studied with some of the great photographers. It was a completely different style of photography with Garry Winogrand. I spent two years with him as my mentor. I remember there was a photographer who did over a hundred magazine covers for Life Magazine. He came to Dallas when I was in high school. I said, “I want to be like you.” It seems like such a glamorous life. He took all these pictures of Marilyn Monroe and all these. It sounded like what a wonderful life. I told him I wanted to be a photographer, and he said, “Don’t be a photographer, be a doctor.” I said, “Why?” He said, “If you’re a photographer, you’re always on the road, you’re compromising your vision, you’re always trying to please your editor.” He said, “Be a doctor then you could take all the pictures you want and you don’t have to worry about pleasing anybody else.” I thought, “Okay.” I did and it really made a difference in my life.

TIP 043 | The Daily Show

Don’t be a photographer, be a doctor. You could take all the pictures you want and you don’t have to worry about pleasing anybody else.

Did you ever contact that person again after?

No, I didn’t. It was a real turning point for me and it made a real difference. I probably have the most well-photographed kids of anybody alive.

Was there a certain accomplishment in your career that you’re most proud of?

Being a good dad and husband is one of my most proud accomplishments. From a work standpoint, the fact that we were able to prove that we could reverse many chronic diseases for the first time by changing diet and lifestyle was a big one, and then getting Medicare to cover our program. The guy that I met with was a guy named Philippe Halsman. He did over a hundred magazine covers for Life Magazine. He probably doesn’t even realize what a turning point that made in my life.

To give the listeners a sense of what you look like, who would play you in a movie?

I always get mixed up with Brad Pitt and George Clooney, I hate that. I’m just kidding. It’s hard to say. Maybe Adam Sandler. Maybe Gene Wilder in his younger days.

Was there a moment or experience that made you feel like you had arrived to some degree? Not that any of us ever truly arrived, but that you were on the inner circle or in the in crowd in the medical world?

Presenting our work at the American Heart Association’s annual meeting 30 years ago, and they highlighted the study showing that we could reverse a major heart disease by changing your lifestyle. They selected that as one of the 30,000 studies that were presented there and held a press conference to announce it. It was really a validation. The most important and significant event was when after sixteen years, Medicare agreed to cover my program. If it’s reimbursable then it’s sustainable, and if you change medical reimbursement, you change medical practice and even medical education. Those were, from a professional standpoint, two of the most meaningful things. Also giving a Medical Grand Rounds as a medical student and I was the first and still the only medical student to actually give Grand Rounds at the Mass General. That was an important and significant event in my life.

For those people who aren’t from the medical world and don’t know what Grand Rounds is.

Grand Rounds is a major weekly conference at a medical school or medical center. Mass General is Harvard’s main teaching hospital. I took a year off after I finished medical school to do a study proving that we could reverse heart disease from changing diet and lifestyle. I invited Dr. Alexander Leaf who was the Chief of Medicine at Harvard Mass General at the time to come see what we were doing. He later confided in me that he thought that was like the most presumptuous thing that anyone had ever done. In Harvard, it’s very hierarchal and you speak when you’re spoken to. If you ever saw the movie The Paper Chase with John Houseman, which was Harvard Law School, he was that same crusty Boston Brahmin character. He said he was so intrigued because he thought it was so presumptions. He actually flew down and saw what we did and invited me to give Grand Rounds there, which is how I ended up there. I didn’t realize then that was a big deal. It was usually for full professors of medicine and so on. As far as I know, this is the first and still the only time that a lowly medical student had given that conference.

Dean, I absolutely love it. That is such a perfect example of your trail blazing style. It sums it up very well.

It’s more “fools rush in” for something to be said for not knowing any better. The same goes to doing my research. If I’d waited until I finished my medical training, I would have been indoctrinated with the idea that these things are impossible, so why bother. There’s something about beginner’s mind that when you go into something, you say, “Let’s find out.” If people say, “It’s a crazy idea. It’s not going to work, but you’ll learn something.” It turns out that it actually did work. There’s something to be said for naiveté.

What hint or riddle would you give people to figure out who you are?

I would imagine most people would have figured out by now.

We’ve given them a ton, but is there any last item that you think we can add?

Nothing I can think of. I’m married to the most amazing woman on the planet, but there are probably a lot of guys who would feel that way. I’m not sure that would necessarily be a deciding factor.

Dean, thank you so much. You have between now and the next episode to figure out who Dean is. If you do, you can win the invitation to me here, The Salon by Influencers. Good luck.