From courtroom to comedy: the unique career of Chicago Comedy Film Festival’s Ray Chao

doritos 2 croppedYou know Ray Chao. You may know him from growing up in Morton Grove or from high school at Niles West or from the Game of Thrones trailer that preceded Jurassic World in theaters nationwide last summer. He currently appears in commercials for Ford Motor Co., HP and in a Doritos commercial he created, hopefully slated for the Super Bowl. The comic actor also has many film credits, including Hell Fire, Cut and a Funny or Die short with John Goodman, to name a few. He is also a writer, director and producer.

He has had a long, successful, unusual career. Years before he appeared on stage and screen, he appeared in Cook County courtrooms as an attorney protecting Chicago’s most vulnerable kids. Now in Hollywood, he continues to mentor. Little Buddies, which Ray wrote and directed, provided one of David Chandler’s earliest roles (now he’s “Derrick” in The Middle).

You’ll have more opportunities to get to know Ray next weekend when he hosts the Fifth Annual Chicago Comedy Film Festival, one of the only comedy film festivals in the country. The Festival takes place from November 6 through November 7 at The New 400 Theater in Rogers Park (details below).

Several films will have their Chicago premiere: Killing Poe is a students-versus-teacher revenge fantasy inspired by Edgar Allen Poe. It was filmed in Chicago’s north suburbs with appearances from Chicago celebs like Dobie Maxwell and Xavier Lamont. Another premiere is Up on the Wooftop starring Dennis Haskins in a stellar-looking Christmas movie about Santa’s wayward dog.

The Festival’s shorts programs have also been beautifully curated. Their themes include “Sex and Modern Love,” “Gender Narrative,”“Fawkward” and “Human Evolution?,” yes, phrased like a doubtful question, one we’ve probably all asked.  Many of the shorts have Chicago roots, such as Pick One for Me by award-winning Chicago comedian Paul Thomas, Gayborhood which takes place in Boystown, and The After Party with Chicago improv icon Dave Pasquesi.  These are only a small sampling of this feast for comedy cinephiles.

Ray will M.C. the films and moderate “Question & Answer” sessions. But you don’t have to wait until then to hear his story. He kindly spoke with me by phone about how he went from courtroom to comedy.


Q: When did you know you wanted a career in comedy?

A: I had a whole separate career in Chicago. I had never performed. I was never a comedian. I was a prosecutor for the Cook County State’s Attorney specializing in crimes against children. That was why I went to law school. I had a very specific goal. And luckily, I achieved it. I really loved being a lawyer. It was fun and challenging and I think I was good at it.

R tue 13 (3)Q: How did you decide on child law?

A: I had been doing graduate work with gangs and wanted to find a way to be even more helpful to the population.  And I thought, I should go to law school. I was working full time, so I wasn’t going to leave Chicago and I needed a part-time program. Then I saw that Loyola had a JD-MSW program and I thought, that’s perfect.

It was the only law school I applied to and luckily, I got in. So I was sitting there the first day of class and they handed out a flyer announcing the child law program starting that fall. What a happy coincidence. Once I learned about that, I still took a handful of social work courses, but eventually, because they were building this child law program from the ground up and it was the first in the country, I concentrated all my efforts on that. Back then it was not a popular area of law.

By chance I had positioned myself in the best way for a lawyer with my career ambitions. I followed their program from its inception and took advantage of all the classes, experts and opportunities. When I graduated three years later, even though I was a newly admitted attorney I actually had an expertise.

That’s how life is. I couldn’t have planned it better.  I’d done coursework. I’d published. I’d kind of created this expertise as the legal field was creating it as well.

Q: How did you go from law to comedy?

A: While I was working I was also teaching law school at Loyola and one of my students said “Hey, I’m performing in a show at Second City. Come watch my show.” So I said, “Okay.”

Even though I was born and raised in Chicago, I’d never gone to Second City and never taken any improv classes. I went to see her show and I thought, “Wow, this looks really fun.” So I started taking classes at Second City and it changed the course of my career.

I started performing and did a little bit of acting, but focused on improv, sketch and stand-up, all the time working as a prosecutor.  Finally, after six, seven years, I thought maybe I should pursue this.

So I moved to New York and I got a position with the city of Manhattan as an attorney and started pursuing acting more vigorously. Got a commercial agent and started putting myself out there.

I did a lot of off off-Broadway, a lot of live theater. I worked with tremendous actors both in comedic and dramatic roles and with some of the best improvisers I’ve ever worked with. I was very lucky and settled in with a couple of groups with improvisers who were actually making livings improvising which is very difficult. But because the New York improvisation market is smaller than Chicago, there’s not a very large demand for live comedy theater.

So I spent four years in New York honing my craft outside of live improv. I focused more on scripted stage, TV and film. And then in 2010, I moved to L.A. and decided I was going to put the lawyering aside and focus on acting full-time. I’ve been here ever since.

Q: What was the turning point? How did you know when it was time to leave Chicago to move to New York?

A: Well, the move from Chicago was the most difficult because I was born and raised in Chicago and it was all I knew. I had not only my roots there, but I was very well established professionally. I was a prosecutor. I was a teacher. I was taking classes at Second City.  I was performing.

People thought I was crazy when I said I was going to move because I seemed to be doing everything I wanted. But a part of me felt that if I wanted to grow as an actor, I needed to go to a larger market.

As an Asian actor, I am limited in a certain way as to how I’m perceived and how I fit into the comedy world or the larger acting world. No matter how you look at it, that’s just the way it is.

I felt I’ve got to go to a larger market because there’s more opportunity. So that was one of the primary reasons. I wasn’t entirely confident it was going to work. It was a big risk. But it worked out well. I really enjoyed New York.

The bigger dilemma was leaving the career behind, leaving that financial security because obviously, lawyers are pretty well compensated. I went from being more financially stable to less financially stable which is interesting because most people don’t do that later in life. You do it earlier in life. But that was the big shift, to say I’m all in and move to L.A.

Q: Was it scary? Exciting? Or all of that?

A: It was a little bit of both. The flip side to leaving a law career is I knew I could go back to it. It was a win-win because I loved being a lawyer and I loved acting. I wasn’t leaving something because I was unhappy. I was looking for something because I wanted to be happier. Once I was okay with that, the scary aspects of it went away.

As I went from Chicago to New York to L.A., the market got bigger and bigger. But there are always connections to Chicago. When people see the training I have from Chicago, they respond really well.

Another aspect is the Chicago community is strong in both New York and L.A., particularly in L.A.  Just last week, I went to a friend’s birthday party. He’s from Chicago and he was saying, “Yeah, Ray was in my first improv show ever in Chicago.” Who would have known back at a Second City beginners’ show that we would be here fifteen years later?

A fight between Kim Jong-un and Obama.
A fight between Kim Jong-un and Obama.

Change is very hard particularly when it’s all encompassing, but because my changes have been from good to good, there’s never ever a downside to any of the changes I’ve made.

Q: Do you find legal skills translate well into comedy and theater?

A: Absolutely! A lot of the skills are the same. When I was in Chicago and teaching at Loyola, once a year I did improv for moot court students. As a teacher I always told law students, law is about communicating. You have two sides advocating on the same issue. Who’s going to be more persuasive? It’s about communication.

That’s why my stand-up is very precise. I’m very descriptive because I like using language as part of the process. I fiddle with words and the way some words are definitely funnier than others. Pacing is also important.

Another aspect of being a good actor is drawing on life experiences and bringing a real life response. That’s what improv is all about, too. It’s not necessarily looking for the funny, but communicating a real reaction. You have to recognize what other people are going through and [seeing so much in court], I had that real life experience.

As a litigator, I was always somewhat theatrical in a certain way even though I didn’t know it. Now that I look back, that’s why I think I was effective in the courtroom, because I was able to convey emotion appropriately. I was able to keep my cool. Personality and presence are also important.

As an actor, I market myself as someone who conveys friendliness and approachability. Those are tools that served me well as a lawyer. You don’t want a lawyer who comes off as cold or uncaring. It’s important for clients, too, and not just in the courtroom. One of the best compliments I received was that clients felt very comfortable talking to me. Sometimes you need to establish that immediately. You meet your client and you’re in the courtroom twenty minutes later.

And so I think that’s my brand in acting, too. I’m the friendly neighbor or the concerned doctor or the empathetic friend. In acting as in law, you need to convey it immediately. It helps that I truly served that role. How scary it is to be in a courtroom if you’re a child or a young person. They might be incarcerated or behind bars and I had to convey not only empathy but a level of knowledge. They had to trust me professionally. I had to convey confidence yet I also had to be approachable. I’ve lived those roles. I think it’s paid off.

Thinking of the parallels, how remarkably similar it is and the rewards, when I worked with a kid who was in foster care or with a kid to get out of juvenile detention, there was only so much I could do. They could take my advice or leave it, but I loved that feeling [of making a difference]. That’s what kept me motivated in court.

Now similarly out in Hollywood, I love working with young actors. I treat them like young adults and I’m very candid. I used to talk with kids about where you’re going to live, why you can’t live with your mom or why dad is an alcoholic. After those conversations, it’s refreshing to have a conversation like, “Maybe your motivation should be, hey, you lost your cat.” It’s all about perspective and these kids are living their dream. How wonderful. The environment is so much easier in the sense that it’s a happier place from the get-go.

The parallels between law and acting are amazing. Having walked in both shoes, I can tell you they help each other so much.

Q: Is there a case that especially stands out from your law career?

A: I remember trials where the victim was a child or very young and really horrifically brutalized. The professionals, the doctors or the nurses or social workers testifying were in tears. These were people who saw these terrible things every day, yet they were showing a side they couldn’t display at work.

Sometimes I draw on that real life history for emotional foundation. It’s very easy if I have to be sad or angry. I think back to those specific instances because they’re very visceral. I remember very much being in the courtroom and questioning these witnesses and hearing these horrific things and introducing the horrific crime scene photos.

Going back to the skill set, when I was in those situations, obviously I had an emotional response, too. I wanted to help those kids and that’s why I was there, but first and foremost as a prosecutor I had to be unaffected to a certain degree.

I was putting on the case and the judges wanted to hear the facts in a more clinical way and although there’s emotion underlying it, I had to do my job despite the emotion brewing underneath. That was a real life acting class. I lived it day in and day out.

Those are all skills that you have to learn. Actors have to keep control of their emotions yet they also have to do a job. They have to remember the lines and they have to know when to show emotion and when not. That’s what I did in the courtroom. These are gruesome cases. We’ve all read about them in the news. But at a trial the facts have got to be presented in a clinical way in order to get the results that you want.

Q: It’s interesting to hear the whole picture, how acting and comedy and law and juvenile law all fit together. I can see the continuity of it.

A: I feel like I’m so lucky because I had no master plan and it all worked out exactly in my favor. I recognize how fortunate I am.

Q: Where and when can we see your commercials?

A: I had a national airing this summer for Game of Thrones. I have a Ford commercial running in the Nevada area right now. I have an HP commercial that is running on the internet.

Something you might not know unless you’re an actor is that often you make content and never see it. With the HP spot, I filmed it and it was only later when I got a check that I thought, “I need to look this up” and looked it up online.

Just the other day, someone said, “I saw your HP spot. It was on Spotify.” Actors don’t know how the content gets distributed. With Game of Thrones I was getting comments like “I saw it on Words With Friends” or “I saw it on Twitter.” Places I didn’t even know had ads.

The Game of Thrones commercial ran before Jurassic World, so people were like “I’m at Jurassic World and we just saw your trailer.” So that was really cool. And yeah, I saw it on TV which means it was playing a lot because it’s so random for me to catch it.  It’s a really fun spot. It was the highlight of my summer.

People assume you’re in something, so why would you not know? I have shows I’ve done that people tell me about or send me screen captures that I’ve never seen. There’s no mechanism to inform the actor. If you call the agency or you call the network, they just don’t have time because they’re on to the next thing. It’s actually kind of a fun surprise because sometimes you’ll look up and you’ll see yourself on TV. It’s a very unusual notoriety.

It’s also fun watching commercials because I’ll know people in them or I’ll see a commercial that I auditioned for and think, “Ah, I could have done that.” Kind of funny.

Q: What is a typical day?

A: My schedule changes every day. I have auditions and production meetings and things like that. It’s a big difference from where I was before. As a lawyer, my time was very structured. Just last week, I had a day where I was totally open, then within 24 hours I had scheduled three auditions and I had a taping. I went from having a day that was completely free to having a day where I was juggling things. So there isn’t a typical day, which is actually exciting.

Just last week, I had a couple of ideas that had been brewing and was running them by some actors and we decided to shoot a couple of videos the next day. We all said, “Yeah, yeah, let’s do it.” It fell into place quite rapidly. One of them is a Halloween theme, so that one is going to come out right away.

Q: How did you get involved with the Chicago Comedy Film Festival?

A: Well, my good friend Jessica Hardy created the Festival five years ago. I performed with her in Chicago and we have always been friends. Even though I moved to L.A., I said I would be glad to help. I serve as the M.C. during the event, so that’s really fun because I get to interact with the filmmakers and actors. I run the “Q & As” and get to interact with the audience as well. Over the years, my role evolved into helping out with the screenings and problem-solving when I can.

Q: How do you all decide which films to accept for the festival?

A: Every festival is different. We’re a small staff. There are only six of us. As submissions come in, the screeners do a first viewing. They either reject the film or advance it. Then it becomes more detailed. There’s a committee that has to review them. It’s not necessarily about the funniest movies because we want to build a program.

For example, with shorts you look for certain themes or trends in comedy. You want a balance between themes repeating themselves and innovation. Programming is a skill in itself. Let’s say you’re cobbling together a program of six shorts. The six shorts have to have some sort of unity. There also has to be a common thread that the audience can relate to.  That’s what comedy is about. We want to relate to people.

Q: Do you seek out films with Chicago connections?

A:  We definitely do and as you can imagine, because we are comedy oriented we get a lot of submissions from Chicago even without seeking them out. But we do encourage Chicago programming to some degree because it is the hometown. It’s so important to have a venue for your work, so we want to support our Chicago actors as much as possible. Obviously, the quality has to be there. Just because you’re from Chicago wouldn’t guarantee acceptance. But then again, we’re cognizant of it.

Jessica is also a very strong advocate of women filmmakers, so we have a specific eye towards women filmmakers because that’s important to our festival.

Every year is a little bit different, but ultimately as programmers we have a responsibility to put out the best work.

Q: It looks like a great line up.

A:  It is. This year’s features are exceptional. The quality of submissions was really great. We had to turn down some really good ones because we don’t have enough screen time.

Q: So why should audiences attend the Chicago Comedy Film Festival?

A: Our audiences enjoy our film festival because it’s a very fun way to gain insight into what’s emerging in comedy. These actors and filmmakers are on the cusp of making it big. The program, especially the shorts program, gives you an opportunity to see a wide variety of filmmakers and different styles. They’re very innovative.

I love going to see studio movies but I have to admit, they’re all kind of similar. I don’t mean that in a bad way, but you know what to expect a lot of the time. But festivals survive on the independent filmmaker mentality. I’m a filmmaker myself. I know what it’s like.  I don’t have money to pay this person or I don’t have money for that location. So what do I do? I have to figure out an inventive way to do it.

The Chicago Comedy Film Festival is wonderful because it’s one of the few film festivals that focuses only on comedy and it’s a great marriage since Chicago is known for comedy. We have features, shorts, web series, but because they’re all comedic it draws like-minded people. It draws the fun, wacky people and when they’re all together it’s unpredictable. Unpredictable, but fun.


The Chicago Comedy Film Festival is on November 6–7 at The New 400 Theater, 6746 N. Sheridan Rd. You’ll find the schedule here and tickets here. Trailers and sneak peeks here.

Send Ray’s Doritos ad to the Super Bowl by clicking here!

You can see more of Ray’s work at


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