Interview: Mike O'Malley on HEELS, his LAW & ORDER episode, his adoration of Arthur Miller and Greg Garcia, and more

In this first part of our sprawling conversation, I do a little gushing about how great HEELS is, after which we dig deep into the early years of his TV career

If you’ve followed my writing through social media over the years, then you probably know that I continue to be completely surprised anytime someone of note turns out to have been a fan of my interviews. Mike O’Malley is one such individual: he started following me on Twitter out of the blue several years back, and when I couldn’t help but ask why he’d suddenly done so, he told me that he was a Random Roles fan, and my mind was blown. We continued to trade the occasional DMs now and then, and we made tentative plans to do an interview at some point, but before that actually came to pass, we ended up having dinner in Pasadena last year when I was in town for the Television Critics Association press tour. In fact, it was through this dinner, oddly enough, that I actually ended up getting what I think was the final interview for Surely You Can’t Be Serious: The True Story of Airplane! But that’s a story for another time…

During the course of that dinner, however, it was agreed that we’d finally get around to doing an interview when season two of Heels made its debut…and we would’ve gotten away with it, too, if it hadn’t been for that meddling writers strike. As a result, Mike wasn’t able to promote anything at the time of season two’s release, and we pushed our conversation off until such time as we felt like it’d be appropriate.

One might argue that it would’ve been appropriate to talk when Extended Family, the series that he created for NBC, made its debut, but at the time, I was exclusive to Q Magazine, and it was a lot easier to get away with doing an interview with one of the show’s stars (Jon Cryer), which is what I did.

When I learned that Heels was coming to Netflix, however, I saw my opportunity to finally make this conversation happen, and Mike was down for it as well, so here we are. It was always destined to be a bit epic, of course, and since he realized belatedly that he had an appointment scheduled for the same day as our interview, he offered to hop back on the call after he’d returned from said appointment, so that’s precisely what we did. As such, this is the first part of the conversation, and the second part will follow as soon as I’ve had a chance to finish transcribing it.

Read on, and enjoy!

How did Heels originate? I know you're not just one of the stars, you're also one of the producers, but you're not the creator.

Mike O'Malley: Heels was a project that was created by a guy named Michael Waldron, who is now the successful showrunner of Loki, and he's got a new show coming out, Chad Powers. But he's the creator and executive producer on Heels, and he sold the script to Paramount Studios, and they then sold the idea for the show to Starz back under the Chris Albrecht regime. They tried to cast it and couldn't find the cast. They couldn't find their Jack Spade. In the meantime, what happened was, Michael Waldron's career as a screenwriter took off. He's written Doctor Strange (In the Multiverse of Madness), he's writing the Han Solo movie, he's writing the new Avengers movie...

[Actually, Waldron has moved off the Avengers movie...and I don't know anything about the Han Solo movie, but this comment definitely has my attention. - WH]

And the people at Starz - Jeff Hirsch - came back and said, "This is a really good project. We should make this." And I had had my experiences with them, which was extremely positively, making Survivor's Remorse for Starz, so Carmi Zlotnik, who was then in charge of all the development, called me up and said, "Would you read these scripts?" And I read the first four scripts, and it blew me away. It really was a bunch of gut-punch moments in the scripts. And he wanted to know if I would come on and sort of show Michael - who had never run a show before - the ropes, so to speak, on show-running this. And then Michael's star kept rising over there at Marvel, so I became the show runner.

So that's what happened: I read the scripts, I loved them, and then we attached some actors, and then the pandemic hit. And I was just trying to get the scripts ready. You know, the first four scripts in particular were in just fantastic shape. And anytime you hear people say, "Oh, the scripts are ready, we're done, they were all written beforehand," once you have production issues... "Where are you gonna shoot?" "Is that actor available?" "Can that actor do the thing that you've written for them in that script?" You're always changing the writing up until the last minute...and sometimes you're changing it after you've shot it! You go back and see that it hasn't worked, so you slide in another scene in a reshoot. So that's how it came to me. I had an experience show-running a show on Starz, it was a great relationship with all of the people over there - I love those people and how they care about television - and then this was a great idea. So that's how it started.

I grew up only slightly caring about wrestling - when I was a paperboy, I remember going with some fellow paper carriers to see Ricky Steamboat - but I really didn't pay that much attention to wrestling until, if you can believe this, I was reading Bob Mould's memoir, and he talked about the period of time he spent writing for the WCW. 

Wait, the guy from Husker Du?

Yeah!

Wow. 

Yeah, so between reading about his experiences with the WCW, watching G.L.O.W. on Netflix, and then movies like The Wrestler and The Iron Claw, and now Heels, it's captured my attention considerably more. And when I was telling my wife about the show, I said, "You don't even have to like wrestling, because at its heart, it's a family drama...and then once you've been sucked in by the family drama, you can really appreciate the choreography of the fight scenes, because it's incredible.

Well, thanks, Will. I think that's one of the challenges of marketing a show about anything that people aren't initially interested in. My wife is not a fan of combat sports, so if you show her a show where two people are standing in a ring and that's the one-sheet, she's, like, "Not for me." And it's the same as if somebody saw a one-sheet with a bunch of ballerina shoes, they'd be, like, "Not my deal. I'm not watching a show about ballerinas." But then you find out what goes into it. So the challenge of a show about wrestling is that most adults have formed their opinion about wrestling: they watch it and enjoy it, they used to watch it as a kid and no longer watch it, or they don't watch it, never watched it, and they're, like, "Why would I be interested in that thing?"

And like anything that people are interested in... I mean, my father sings barbershop music. He just had his 50th year in the Barbershop Preservation Society. Every year he goes to a convention and they have a competition, and barbershop music is sung in choruses and quartets all around the world, but especially in North America. Other people are, like, "I'm not interested in hearing four-part acapella harmony! I'm not interested in that!" So imagine setting a show there. Now, granted, wrestling... 25 million or however many people watch it, and Netflix just spent a lot of money investing in wrestling. What we hope this show does is explains to people who love it and don't love it what goes into it. That's what we love about this show.

That season two premiere... I don't think it would've worked as the first episode of the series, because you need to set the stage for the present day first, but having done that, it was fantastic the way it stepped back in time to offer kind of a belated origin story, and an extremely impactful one at that.

Well, thank you. We spent a lot of time thinking about that, because everyone wants to know, "Where did this thing start?" And once you get to know the characters, you want to know, "Why are the stakes so high for them?" Now, everyone can understand how, if you're an actor and you're doing Death of a Salesman in some small town, and Friday night is opening night, and there's a hundred people who're gonna come... You've gotta learn your lines. You want to be great. Or there's people who are playing on the baseball team or the basketball team at their local high school, and they care about that as if they have a championship match. And that's another thing that we wanted to show in Heels: their lives are what is happening to them right now. They think that they're gonna be happier when they get success or money or fame...and why wouldn't they? Because everyone's struggling, and everyone wants to be seen, and everyone wants to work a job where they feel as if their heart is attached to what it is that they're doing, so it doesn't feel utilitarian. 

So really looking at what goes into a wrestler's pursuit, the discipline that they have to have with their weight training, with their stunt training, with being a good actor or performer on the mike, crowd relations... You know, you're just trying to get people to love you...or hate you! And I think what also this show is about... You know, America's great because you can pursue whatever you want. That pursuit has emotional costs. And sometimes people pick the wrong dream. And what do you do when they do that? What do you do when someone picks the wrong dream and they don't know? It's all around us, examples of people who lost their lives, lost their happiness, because they thought they could do something that they can't do. And why is that? Because you've put in your hands... I mean, it's just like us! We make the show, and you talk to people who make television shows and movies all the time. If what you're attaching yourself to is how what you've made is received, then you're in trouble. Now, that doesn't mean that you shouldn't think, "Well, does the audience understand this story? Is this something that's gonna draw people in, or is it gonna offend them? Is this something that's lazy storytelling or too idiosyncratic in the storytelling?" But if I attach all of the meaning of how I do what I do is reviewed or how it rates, then I'm not living my life. 

It's interesting about Heels. For a time, it had vanished off the Starz platform, and it almost felt like when you told people about it, because there was no place for them to really watch it, it was like saying, "Well, if you'd only seen this one-act play I did in upstate Vermont, it was amazing. If you could only have seen it!" And it just lived in your memory. And what I think is so awesome now is that because it's on Netflix, we can actually go and tell people to watch it, and they're having an experience all anew watching it. 

Unfortunately, I can relate to that, because I did those nine months at Q Magazine, and then within a week or two of shutting down publication, they'd also shut down the website and wiped it from the 'net. Except for the Internet Archive, of course, but the principle's still the same.

And it's so hard, right? I mean, listen, I've had that situation where I'm, like, "God, I had this great article about this thing I did," or I did a great interview, and I go to link to it...and the hyperlink's dead! We did a lot of stuff in preparation of getting ready for season two, but we couldn't promote it during the strike. So I'm realizing now that I never even posted all of these great articles that were written about it. So now that it's on Netflix, I'm finally getting a chance to do that.

Well, I want to ask about stuff in your back catalog because, y'know, that's what I do. First and foremost, how did you find your way onto an episode of Law & Order way before you ever had your own series?

Okay, well, what happened was, I was an actor in New York, and you go to acting school, and back then there were a lot of different places where you could just go study acting, and the big thing was when you were gonna be in their showcase, where the people at the school - teachers and whatnot - would invite agents and casting agents to come see you. And I went to a place that's no longer there now, but it was called the Gately / Poole Acting Studio. I had a great acting teacher, Laura Henry, and I was in the showcase. And I did a couple of things, and I got a person interested. I didn't sign with them, but they were interested, and they submitted me for Law & Order. And I don't think I got it the first time, but then I got offered one line. And it's funny, because my line was, "Sarge, we got a fresh one here!" [Laughs.] 

Of course, I forgot my glasses, and I'm getting cued by the A.D. about 200 yards away, and it was this massive scene at a Mafia burial ground. So they had to reset the whole scene because I didn't have my glasses on, and I didn't wear contacts at that point - very stupid - and so the A.D. is jumping up and down for me to say, "Sarge, we got a fresh one here!" And we had to pull this guy out of a grave, and this extra, who had to have been in his late sixties, was tasked with helping me. And he was not helpful. And the guy who was playing dead... He was playing dead, so he was dead weight! So I've got a bad shoulder, I've torn my rotator cuff, I've got this other guy, and I'm trying to yank him up, and I'm, like, "Can the dead guy at least push with his legs a little bit? He's out of frame! Can't he help us out?" I'll never forget it. "Sarge, we got a fresh one here!" 

What I'm really proud about is that it was first season Law & Order. Not a lot of people can say, "I was on Law & Order in the first season." Since then, I've been asked to come back and do some episodes, and the schedule hasn't really worked out, but...that was, what, 1991? I'd just gotten out of school, and I was going home for Christmas, and I remember Chris Noth and George Dzundza and Michael Moriarity, they were all great. Also, we were shooting at, like, 2 a.m. on a Friday, and you could just see these guys, they're getting their coverage... But it was awesome, because that was back in the days when there were just so few networks, so if you could get on a show that was actually on a network, it was a real credit, even one line. So I think we had a party at my house. It was awesome. [Hesitates.] Dude, this is gonna be, like, a two-hour conversation. I'm gonna have to call you back after this appointment. 

I'm resigned to that. You probably should be, too. But I promise I won't hit everything.

Hit everything, man! I'm happy to talk about it!

Well, in that case, let's talk about Life with Roger, since that was your first gig as a series regular.

Right, so what happened was, after [Law & Order], I then went and hosted a couple of shows on Nickelodeon. I was explaining to somebody about that this past weekend, because it's hard for people to think about this now who are younger than us, but...no adults watched it. There was no animation, really. They had that show from Canada, You Can't Do That on Television, where they would slime people, but there was no programming for any adults, so no one watched it. So they said, "Do you want to go do this game show?" And I think I was paid like $250 an episode.

But I'd just been reading Charles Grodin's memoir, It Would Be So Nice If You Werenj't Here, about being an actor in New York and starting out, and I think it's one of the best memoirs about being an actor, because he's just, like, "Work with people who are doing stuff. Obviously, don't work on something that you think goes against your values, but if you're working with people, the odds are that those people who are working and making something are also trying to make great things." Famously, Laurence Fishburne met John Singleton making Pee-Wee's Playhouse, and Laurence Fishburne had already been in Apocalypse Now, but you work because you want to work. 

Anyway, as a result of the Nickelodeon stuff... They were very supportive of me, and I wanted to write plays, so I'd put on a couple of different plays. Just my friends and I, in New York, just 99-seat theaters. And what's interesting is that when you're young and you're in your twenties and you're just trying to make stuff happen... Back then, there weren't many video movies. Certainly not what there are now. Putting on a play and having people come see you led to starting to get auditions. Also, there were so many more pilots being made. So what would happen would be, after awhile all the good parts were taken, and they're still trying to cast these pilots, and they're making 30-40 pilots a year, and you could just be somebody who gets cast in something, and then that pilot gets picked up and takes off!

So for me, I'd done a CBS pilot called Emmett and Earl, which was a Worldwide Pants / David Letterman thing, and that didn't go, but it actually ended up turning into a series called The High Life. Adam Resnick wrote it, and...I did not go forward with that project. [Laughs.] But anytime you get cast in something, it helps you get cast in something else, because people are, like, "Well, wait a minute, who's this guy?" And it gives your agent something to talk about. So Life with Roger was an NBC pilot at the height of Must-See TV time, and it was a last-minute late flyer. Here's an interesting story: I went out to L.A. to test for this pilot, and I had to ride around in a car with one other guy, and it was gonna be me or him. And it was Paul Giamatti. So everything's turned out fine for Paul.

He's made it work.

But he couldn't have been a nicer guy. And I had seen Paul in some theater in New York, and I was just blown away by him. So anyway, I get that part, NBC passes on it, but that was when the WB had just started, so the WB - since it was a Warner Brothers pilot - picked up Life with Roger, and we made 20 episodes. 

I've at least seen the pilot on YouTube.

Yeah, it's fun.

It is. You and Maurice Godin had great chemistry.

I love Maurice. Maurice is a great actor. I love that guy. You know, John Wells and I made a pilot called Prodigy Bully a few years later, and I cast Maurice in it. He was great. 

Just as a sidebar, I know you're subscribed to my Substack newsletter, but I don't know how deeply you've delved into it. I do a regular feature called Pilot Error, where I write about pilots that never went to series.

Oh, I have to go back and read them! That's a great idea. I'll have to go back and dive into them. 

That's the book I want to do: either brief oral histories about pilots or even just short pieces that examine pilots that were notable for some reason or other.

Yeah! And as I know you know, these pilots are where people end up meeting people that they then want to cast in other things. It really is an interesting story to be told about how many people make shows - whether it's one season or just a pilot - and it doesn't really happen, but then they meet people in the process. The rate of failure in television is just so... [Sighs.] I mean, it's just an insane business. But you learn. One of the things about the multi-cam world is that there were so many multi-cam pilots being made when I was coming up that you could really get experience doing it. Almost like the minor leagues. So by the time I had done Yes, Dear, I had already done 20 episodes of Life with Roger, a pilot that I did with Sam Simon, another pilot that I did with David Letterman... Y'know, that's a lot of hours before you finally get something that goes. And it's not an easy genre to just succeed at. You've got to learn your shit.

Not to mention the fact that you literally had a show with your name in the title before Yes, Dear took off. 

Yes! I mean, that was a limited series. If there was a limited-series comedy Emmy, maybe I would've gotten it back then. [Laughs.] Because it was very, very limited. That was in 1999, so that was at the height of Must-See TV, and that show was on after Will & Grace. Because what a better pairing than my audience and a guy from Boston in a baseball cap?

An absolutely spot-on pairing.

Spot-on. I mean, it feeds right into it. [Laughs.] 

And that was with Will Arnett, which had to be pretty early in his career. At the very least, it's three or four years before Arrested Development.

Yeah, Will... I'm gonna be 58, Will's a few years younger than me, so I was 33 at that point, and I think he's four or five years younger than me. So Will and I were friends in New York and just hung out, loved each other, great guy, and...it was like a dream come true. I mean, that show had Will Arnett, Kate Walsh, my sister Kerry, who's an extremely accomplished actress, Mark Rosenthal, who... Mark Rosenthal and Missy Yeager had starred in Ken Lonergan's play This Is Our Youth, that was in New York. Missy was a great friend, Kate was a friend, so it really was like a dream come true, because these guys all had to go through the process of testing and getting picked. But the show... What's interesting is that I made the deal with Warren Littlefield, and...here are the executives on that team: Warren Littlefield, David Nevins, and John Landgraf. Those three guys left...and not much later after that, the show was canceled.

I'm shocked - shocked! - to hear that. There's certainly no history in Hollywood of shows failing after the team behind them leaves.

Oh, yeah. [Laughs.] But they were all awesome guys. And I've worked with John and David since then. Not with Warren, though. I almost worked with Warren. They were all great, though. But then a new team came in, and...I dunno, they didn't like the show.

John Landgraf is one of my favorite network exec to just sit and listen to when he's delivering a TCA presentation. 

He's really smart. He's really smart about television, he's really smart about story, and he's really smart about what the audience wants. And he's always been that way. If you were to meet John today, he was like that 30 years ago. Just smart. And a thoughtful person. Intentional in his listening, intentional in what he says. 

You can always tell when he's responding to critics that he's never giving a throwaway answer. He clearly considers his responses.

Oh, yeah, 100%.

Once you did land on Yes, Dear on a long-running hit, or at least a long-running commercially-successful series... I honestly have no idea how popular it actually was!

Well, listen, man, we did 122 episodes. Look, here's the way I feel about that: I came on that show six months after I'd had this very public failure. Nowadays shows completely go away and people have never even heard of 'em. I just worked on a show with Jon Cryer and Donald Faison, and people were, like, "What? I didn't even know that that was on!" Back then... Again, it's harder for people who are younger to realize this, but there was nowhere to hide. If they picked your show up, they canceled a bunch of other shows, and then there's all this new development that wanted your show to not succeed so they can get their new show on. That was something that I didn't really pay attention to until I got farther along in my career, and then I realized, "Oh, gosh, yes, of course: this is a competition. Every night you're competing. Your show is trying to beat the other people." So our show fit very well into what CBS was doing on Monday nights, and we made 122 episodes. And trust me, there were people trying to take our timeslot and beat us, and they didn't. 

I watched it with some regularity and enjoyed it. I mean, you and Anthony Clark were great together, and the same with you and Liza Snyder.

Yeah, I love Anthony, and I love Liza. Look, man, I'd still be doing that show. I remember when we were doing that show, Ray Romano and Phil Rosenthal would be, like, "I don't know if we can come up with another season," which was probably just a negotiation tactic on their part. But I was, like, "I'll come up with another season!" [Laughs.] "We'll be fine!" Alan Kirschenbaum, who was the co-creator of that show, he and I used to joke, "Yeah, man, we'll make this show 'til they kick us off the lot!"

It wasn't until years later that I realized that Greg Garcia was the other co-creator of the show. Although I guess that's because he wasn't Greg Garcia yet.

But here's the thing: anybody who ever met Greg Garcia, from high school to college until he was working on Family Matters to Yes, Dear, knew that he was one of the funniest people on the planet and a really, really good guy. So before Greg Garcia made Raising Hope and My Name is Earl, anyone who was working with him knew how funny and great he was. So it wasn't a surprise to us that he went on to great success. 

And clearly there are a lot of people who still have dedication to him, given the repeat performers he's had in his series.

Oh, yeah. They don't make 'em like him. He's just a really, really great guy who is funny, loves his friends, loves his family, thoughtful... I just can't say enough great things about this guy. That guy... They should just let him make whatever he wants. I mean, he has three shows that've gone into syndication. The guy is big time.

How did you enjoy getting to work with Jerry Van Dyke on Yes, Dear?

Oh, my God. I mean, listen, Jerry couldn't remember his lines so well. But he was funny. We would joke, because he would stutter a bit. It wasn't a natural stutter. It was reaching for the line and what it was. But he was just fun. I mean, think about it...we did an episode where, because he owes money to Johnny Bench, Frank Robinson, and Ernie Banks, we get into a fist fight with these guys. So suddenly I'm in a fist fight with Ernie Banks, Frank Robinson, and Johnny Bench! I mean, this is the thing: that's what it was when you were on a show back in those days. The guest cast that we had on that was fantastic. Tim Conway! Jerry Van Dyke! Vicki Lawrence! Dan Hedaya! It was just a great group of people.

To this day, no one has thrown me off my game more quickly in an interview than Tim Conway.

How so?

He was supposed to call me, so I picked up the phone and said, "Hello?" And he said, "Will Harris's office." 

[Cackles.] He was a great. What a great guy Tim was! I mean, just an old-school, thoughtful guy. He'd write notes and tip out all the people who worked on the show or the production assistants. He really knew how to do it right, that guy. What a good guy. 

Speaking of stars, who would you say was the first person you met where you had to keep from going full fanboy?

Well, definitely Arthur Miller. 

Wow.

Yeah, look, y'know, every actor who wants to be an actor... There's not many playwrights that everyone has to read in high school, but you're reading The Crucible and Death of a Salesman, and you see the power of their storytelling and their craft. And then you go to study acting, and...I like to do comedy, but I also was very drawn towards how dramatic plays and films made me feel. So when I was in my late teens and early twenties, everybody wanted to be Sean Penn, Meryl Streep, Jack Nicholson. And Arthur Miller was somebody who...I read his memoir, and then I read most of his plays, if not all of them, and then I started to write more or want to write more. And he wrote some incredible books and essays on dramatic writing. So I just thought he was this titanic figure.

So I flew across the country to meet him at a book signing...and I tried to take a picture like I was at a fan convention. [Laughs.] I was, like, "Can I get a picture with you?" And he wasn't taking a lot of pictures. This is, like, a New York Times book thing. And he just goes... [Groans slightly.] "Uh... I've got a lot of books to sign..." And my wife is, like, "Just get over there! Just go!" So I'm, like, crouching down next to him. I look like a college cheerleader who's off on the side, half bent next to him. I'm trying to think if we had kids at that point. Maybe we didn't. But, yeah, we flew across the country to do that. So that was a big one. 

Letterman, obviously, was another one, because I was testing for that pilot. You know, it's interesting: you meet people who can have an impact on whatever you're gonna do and the opportunities you're gonna get. Look, I'll be quite honest with you, I've worked with a lot of people, and when I was doing Sully, I'm in my fifties, and the next thing I know, I'm acting next to Tom Hanks with Clint Eastwood directing. Now that's a reason to know your lines. Because you're very aware of who you're sitting there with, and you've got to forget it. Tom Hanks is there, and you're asking him a question. "How many drinks did you have, Sully?" [Laughs.] By the way, I like to joke with people who say, "You're so mean to Sully!" I say, "All I did was say, 'Did you have any drinks?' If Sully had said, 'Yeah, I had a six-pack,' case would've been closed, okay?" 

That's the interesting thing that happens when you meet someone that you've watched. Suddenly they're in front of you, and it's almost like you've stepped through the looking glass...and you've got to forget that. But, y'know, I've worked with a lot of big stars, and I'll say that Eddie Murphy, George Clooney, Tom Hanks, Sandra Bullock, Julia Roberts... The best ones are big, big stars because of how approachable they are. And all of those people are great and were great to work with. 

You don't have to name any names, but have there ever been any disappointments?

[Long pause.] Nope. I've not had disappointments. I mean, I'm really thinking, but...no. I've been very lucky in that way.

Okay, I know you've got to get to your appointment, so we'll regroup afterwards, but as a closer, a buddy of mine on Bluesky wanted me to ask if you're going to the Buffalo Tom event later this year.

[Excitedly.] I am! 

And I swear to you, immediately after reading that, I popped over to Facebook to check out the post where I'd said I was going to be interviewing you, and who should have just "liked" it but Bill Janovitz. 

Do you know Bill?

Only virtually. We've been Facebook friends for, like, a dozen years. I think we've traded a couple of DMs. But I've never actually talked to him or anything. But he said of you, "He's one of the great ones."

Buffalo Tom wrote the theme song to The Mike O'Malley Show.

That I didn't know. Although I did know that you'd used one of their songs as the theme to Extended Family.

Yeah! Buffalo Tom played at the rehearsal dinner for my wedding. They are my favorite band.