Inside the Boom and Bust Cycle of Standup Comedy with Jordan Brady

Jordan Brady’s love of comedy has carried him through two great comedy “booms” and “busts” over the past 30 years. Although he was a highly active comic during the late ‘80s and early ‘90s, Brady’s interests turned towards directing and producing. His experience in comedy and love for the art of stand-up led him to make I Am Comic in 2010, which presents deeply personal and insightful interviews with comedians such as Louis C.K., Phyllis Diller, Jim Gaffigan, Janeane Garofalo, Sarah Silverman, and Dave Attell.

More recently, in 2014, Brady released I Am Road Comic, which focuses more specifically on the unique issues that face comedians who take their act on the road, often to diverse and unpredictable venues around the country. This time around, Brady gathered interviews with comics like T.J. Miller, Maria Bamford, Pete Holmes, Marc Maron, Doug Benson, Jim Norton, Judah Friedlander, Alonzo Bodden, Jen Kirkman, W. Kamau Bell, Nikki Glaser, and Kyle Kinane to recount their experience of “the road” as comics come to know it. He presents road comedy for what it usually is: a march into a small, unfamiliar town, in a strange bar, where nobody who knows who you are.

I recently had the opportunity to chat with Brady over the phone about his experiences on the scene through the bang and bust of the ‘80s and late ‘90s, where he thinks the scene is now, and what really makes for a great comic.

So what are up to when you’re not filming standup specials for Maria Bamford and Ari Shaffir?

You know, it’s funny: I thought that would lead to more specials, but I think it was the beginning of the end of the big-budgets. Like, Ari and Maria, their first specials were both for this now-defunct website called “” They didn’t know what they wanted to be, and they had a good splash with Ari, and they had Maria’s, and they got the New York Times review and the LA Times came out, it was a big splash. But then after Maria and Ari, I don’t know what they did. They just did, like, five comics for a $10,000 shoot. I think they shot themselves in the foot.

Since you have real, tangible experience with directing and producing for actual companies, do you find that the glut of self-produced DIY documentaries, specials, and the like make it more difficult for you to work independently, or does that not affect you at all?

Well, the filmmaking tools being more accessible to more people, I think, has collectively lowered the bar of the quality of The Special. Right? Because more people are doing a special before they’re ready. But of course, that one gem, that one “diamond in the rough” now has more of a possibility of reaching the masses. But just like the word processor didn’t make a bunch of better screenwriters, the filmmaking tools do not make a bunch of better filmmakers.

I think it definitely made it harder to make a profit from documentaries, because now there’s a glut of them. If a comedy fan were to compare I Am Comic to I Am Road Comic, visually there’s no comparison. With I Am Comic, I had cinematographers helping me with interviews of the comedians, and then I used a Prosumer camcorder to follow some people around.

But  with I Am Road Comic, I just used my high-end camcorder for the very reason that you’re talking about. But it’s going to be the content that’s makes I Am Road Comic stand out. It’s not that I used a great camera, it’s that I had TJ Miller on the street, it’s that I had Marc Maron in his garage, and Pete Holmes at NerdMelt.

Right, and I think I Am Road Comic felt more straightforward. You showed this very straightforward portrayal that is road comedy: a show at a kind of scary venue, in some small town, where – and even more to the point, which I really liked – the audience isn’t people the comics drew, they’re just people who are at that venue.

Well, that’s a good observation, because one could do I Am Road Comic and follow Todd Barry or Brian Regan or Jim Gaffigan, and they’re doing these theaters and mid-size venues where the audience comes out to see them. But this way – you’re absolutely right, the venue was the draw, and that to me is a road comic that – I mean, let’s face it, anybody could go on stage and say, “Oh, I was on this show or that show.” I could go on stage and say, “I was on Comedy Central.” It happened to be 1990, but whatever. That credit doesn’t mean anything anymore. Premium Blend, people don’t even know it’s off the air. “You’ve seen him on Premium Blend!” That doesn’t mean shit anymore. The Tonight Show doesn’t even mean anything.

Right. Yeah, you can’t get famous at standup as a standup, I think that’s the other thing in that. But, yeah.

Wow, I can’t believe you said that. “You can’t get famous in standup as a standup.” That was one of the questions I would ask a lot of the comedians. Brian Regan is probably the one exception … not Louis C.K., not even Jerry Seinfeld, because it took Jerry Seinfeld playing Jerry Seinfeld in a TV show called Seinfeld. It took Louie to make Louis C.K. Now he happens to have great standup and he’s prolific, but I would say people know him as the guy from TV. Brian Regan is the only guy I can think of…

And that just speaks more to the point that road comedy, especially as you caught it in your documentary, its reality. If someone is saying, “I want to do standup and I only want to do standup,” then that is the reality of just doing standup.

It’s true, and it’s not glamorous, and I think circus folk may be on the same rung of the showbiz ladder as what we did in I Am Road Comic. What’s great is that there’s a freedom to it. Doug Benson loves going on the road and has found a way to manipulate life around the standup, whether he’s going to roller coasters or doing his podcast. He’s made the road his bitch.

I was at a party last night and talking to someone, and she’s like, “Oh, I love WTF [With Marc Maron]. Actually, after I listened to the podcast, I went to see Marc Maron’s show.” She didn’t know him as a comedian. I mean, she knew he was a comedian, but she was introduced to him from the podcast.

There’s another level that I think would be a different documentary, and it’s sort of that “DIY” show, where you’re still not the draw, and the venue’s not the draw, it’s the one night of comedy that the comedian has promoted becoming the draw. Phil, you produce your comedy shows, right?

That to me is an interesting subject, because with enough social media prowess, you could probably leave New York and go to Duluth, Minnesota and just be like, “I’m coming to town!” and enough people would be curious and you’d come out, and then if you went back six months later, you’d have those same people come back if you did well.

You know who really perfected the road? Country stars, country music acts, as early as the ‘40s and ‘50s, because they would do honky tonks.

I did this mock documentary about country music. Dana Gould’s in it, and Wayne Federman, and David Koechner, Kathy Griffin… it’s pretty funny. But it’s old, it’s like fifteen years old. We interviewed Willie Nelson… to this day, Willie Nelson doesn’t really understand that he’s in the movie, because we had to wait until three in the morning for him to come out of his trailer, billowing with “Cheech and Chong” smoke, outside of a music festival.

He told us in the interview, “You know, man, listen: you do a show, and then during your break, you go around and say hello to people, and maybe have a beer with them. And then when you come back, there’s going to be a connection. Now, they don’t expect that you’re going to remember their name, because they know you’re meeting a lot of people, but you’ll remember that face, and you’ll give them a smile and they’ll smile. That’s a connection, they’ll be fans for life, and that’s part of the joy, is knowing that you got these friends out there.” He was so sincere about it.

People think it’s about going from one place and then just skipping to another, but you should connect with the community as well.

Right, because that’s the ego. The meet-and-greet, you can still have ego. Without the ego, no one would want to meet you. But you show humility and appreciation for fans. I mean, this is turning into a deeper conversation, but comedy, it’s bouts of ego and humility that will give you a long-lasting career. Are you in Manhattan, Brooklyn? Where are you?

I’m in Manhattan.

In Manhattan it’s probably harder. Like, “Yeah, like I want to shake your fucking hand.”

Yeah. You only really get that kind of friendliness from out-of-towners, basically.

Right, they’re enamored with what you’re doing. Let me ask you this: do you have a mailing list?

No, but I’ve heard it’s the way to go.

Any “content creator” should have a mailing list.

Before there was e-mail, there was a guy in the south… I don’t know if he’s still alive, James Gregory. He billed himself as “the funniest man in America.” He was never on TV, but he would kill all throughout the south, from Myrtle Beach to Fort Worth. And he toured out of his car, he used to be a salesman. This is in the ‘80s when the comedy boom was starting.

I would go to the south as a cynical young man, I’d play these clubs, and I’d middle, and it was that dream of partying, and being the middle act was really easy. And you would always hear about how James Gregory was there the week before and he sold out the show and they had to add a second show. I’m like, “What the fuck is this guy’s secret?” Because he was telling old jokes. People would have bumper stickers that he sold after the show, and t-shirts.

His secret was a mailing list, like a pre-stamped postcard that he would hand out at the clubs, and they would be on every table in the comedy club. He would send that postcard back with a stamped date of the club and the time.

The ultimate DIY comedian.

Yes! It was the ultimate DIY, and he used the clubs as his venue, and then the clubs wanted him. But people would come back to see him just like Willie Nelson, because he was selling shit after the show, he got their address, he would inform them a month before he was coming back, like, “Save the date, on the 16th, I’m going to be at The Yahoo. Laugh it up!”

So you were a working comedian throughout the ‘80s and into the early ‘90s. You witnessed the comedy boom from both ends: its explosion and its implosion.

I was understanding of the fact that I was a benefactor of the boom, because there were clubs popping up that needed someone willing to drive the headliner. I had a ‘68 Volkswagen that I would have to put oil in every day – I had to put in more oil than gas – and pick up a headliner at the Washington, DC airport, and I would drive him around for three weeks, and valuable stage time.

So I worked my way up through that, and I think I was ahead of the curve. I remember Dana Gould… we’re the same age, we started around the same time, and we would run into each other, like, at the Atlanta Punchline. There were shows Tuesday through Sunday at a lot of those places. Comedy was so huge.

Then in the late ‘80s, when you’re doing your fourth Evening At The Improv set, and your third VH1 spotlight, you’re realizing, “Oh, who’s going to go out to a club when it’s on TV every night?” All the clubs closed. Then in the late ‘90s, Comedy Central kept putting standup on, but the clubs were all closed… People were like, “Oh, standup’s cool again!” That was like the second boom. People wanted to go out to clubs and then the clubs were a little hipper. You know?

Yeah, and you got that wave of alt comedy, and that took on a life of its own.

Alt comedy became mainstream. When alt comedy is a choice, then it’s not alt anymore.

I think there was a second implosion, really, around… I don’t know, 2005? 2007? There were just so many albums, everybody had an hour special, everybody had a half-hour on TV. And now I see people defining their own “comedy brand” and becoming huge.

Was it that that shrinking of comedy in the early ‘90s that pushed you into directing more?

When I was your age – wow, I just said that – I was doing more non-standup television and standup on the road. I did a show on MTV and I did a kid’s show on NBC. I started directing this kid’s show because it was efficient, and I really had an affinity for it. So it was less the implosion of comedy and more, like, “Oh, I stepped off the boat before it crashed into the beach.” By coincidence. I wish I could say I was so smart that I saw the thing coming to an end.

I mean, I saw the writing on the wall. I used to do colleges. One year I did fifteen colleges and the booking agent said, “I wish you’d stop going on television.” I go, “What do you mean?” Because I did two or three dozen of those crap cable shows. He goes, “Well, because you’re ruining all the material.”

Cable was definitely part of the curse and the blessing for standup. Everybody had seen it, they knew the bit, you had to come up with a new bit. They love seeing the one bit, they love seeing Gaffigan, but he can never get away from doing “Hot Pockets.”

Do you think it’s as simple as an explosion then an implosion and then another explosion? Do you think that we could be in another implosion, or would you say that technology has kind of “muddled the crystal ball,” so to speak?

Wow, that is a great question. I’m going to say, for sure technology has muddled it, but I think that’s going to cause an implosion. We’ve already seen the $5 special implode. The $5 thing exploded. God bless the king, Louis C.K., for not just making it available to the masses, but he pioneered the technology, and more importantly, he created a culture that respected the five dollars when he said, “Hey, I made this myself. Please don’t steal it, just pay the five bucks.” I think he changed people’s perception about stealing an artist’s work.

The worst thing he did was put it at five dollars. I mean come on, Louie, seven would have been a little better … because no one else had the fan base to follow it except for the funniest man in America. So when Maria came out with a five-dollar thing, she actually did really good. I think Todd Barry did one, then Aziz tried one… But then, now everybody’s doing it, so it’s like, “Oh, comedy is just a five-dollar thing.”

It kind of mirrors the way that comedy was so overexposed on TV in the early ‘90s. What do you think pulled comedy out of that slump last time, and do you think it would be a similar scenario this time?

I think the answer is always going to be the same: what’s going to pull comedy out of the downturn, or the valley, and go back up to the peak, is going to be a funny comedian that makes a connection with the audience. Literally, it sounds corny, but it’s always in the hands of the comedians. Who will save us?

When someone new comes onto the scene… like, go back to Sam Kinison. There was never a comedian like Sam Kinison. I’m not even the biggest fan, but he would slay me. He was just so balls-out in your face. That ran its course, and I don’t know what that did for comedy overall, I think he was sort of the perfect storm of comedy boom and a crazy, funny madman. Louis C.K. definitely pulled us out of something and then took it to another level. What’s next? I have no idea.

It feels like comedy’s becoming so much about niches now, too. If you want a type of comedy that’s really dorky, you can go for Mike Lawrence or Myq Kaplan. If you want someone who’s angry and tells unadorned truth, you’ve got Bill Burr, you know?

Right, now it is more made-to-order. And that’s good news, that now the audiences can enjoy the niche marketing of a comedian, or that the kind of comedy they like is more accessible, and I think that’s totally due to technology.

But that does also mean that you don’t need to be in one of the main “comedy hubs” so much anymore. Do you think that we’re going to eventually see the death of the “comedy meccas,” i.e. LA and New York?

Never, never, because people will always pay money to be in a room with a funny comedian. Goes for famous people, too. I think if we agree that it takes more than comedy, more than standup to make a standup famous, then these funny people are going to rise to the top in a city that’s either New York or LA.

I moved to San Francisco as a young comedian and stayed there less than a year, because there were some of the greatest comedians in the world, and so funny, they could riff all night, and were just so unique, and no one’s ever heard of them. And for years, no one ever heard of them. And I don’t think that the internet’s going to change that.

You had the general I Am Comic, and then you had I Am Road Comic, I don’t know what your plans are, but I think the fact that you narrowed it down to a specific segment of comedy, to make another documentary, speaks to niches as well. Niches, not just for audiences, but for comedians themselves.

Yeah, the third one will be either, like, I Am Boat Comic, because there’s old dudes that are still doing Louis Armstrong bits on the cruise ship for the old folks, and then there’s… like, Doug Benson’s going to do a rock-and-roll/weed cruise. And then I think there’s a chain out of Vegas that’s booking some cruise ships. So it’s going to be more like a comedy boom on the boat. Maybe that’s the name of it, Boom On The Boat.

In your experience both from I Am Comic and I Am Road Comic, what is the single greatest thing you learned while you were doing those?

No, I’ve been asked this before in just casual conversation, and it’s a hard question. But I think what I’ve learned is: it’s the singer, not the song. What’s better to have: a great performer or a great writer? You need both.

Jordan Brady also has a weekly podcast, “Respect The Process,” for those interested in directing and producing.

Phil Stamato lives and writes in New York, where he may also be seen standing up and telling jokes.

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