When the last episode of Conan airs on TBS tonight, it’ll be a pause that feels a lot like a stop. The truth is, no one knows what Conan O’Brien will do with his announced new HBO Max series (which is set to debut in 2022). We have no idea about budgets, scale, ambition, or connection to past things like “Conan Without Borders.” And with that uncertainty, we have to accept that whatever comes next may not include Andy Richter, Conan’s longtime sidekick and comedy consigliere. We have to accept it because it sounds like Richter has.
To be honest, I went into our Monday conversation unclear about how much Richter would or could say about the future knowing that nothing had been announced officially. But right at the start, he mentioned the word unemployed and spoke about how he’s going on auditions, attached to a game show concept, developing ideas, and potentially looking to get back into directing commercials, which he’s dabbled in previously. Officially, he’s in wait-and-see mode as it pertains to another ride beside O’Brien. It really does seem to depend on what the idea is, which sounds like the healthiest thing in the world if you divorce yourself from how much you love the two of them together and want to see more.
While Richter seems to be in a good place about his future (“I’ve had my moments of like, ‘Holy shit, this show is ending!’ But it’s mostly just having faith in things working out okay, and looking forward to new opportunities”), he doesn’t quite know how to deal with all the kind words people are saying about the show, the legacy, and what he and O’Brien have done on TBS and on NBC before it. Which is a shame, because we talked about that a fair bit and, more specifically, how the show managed to stay flexible, fresh, and relevant to various age groups.
So you’re not continuing on with the new show in any capacity, or is that still up in the air?
It’s up in the air because they can’t settle on what the new show is. That’s the source of the… I don’t know, the lack of information. It’s just that there isn’t any information. It’s nothing… And nobody’s attempting to deceive anybody, and there’s not anything really interesting [laughs]… besides just a difference in what the next show should be and what will work.
Are you interested in continuing on or you’re just going to wait and see what it is?
Wait and see. I mean, that’s just how I do things, that’s how I’ve always done things. I don’t know if it’s my improv background, but I just wait and see what happens and then make the decision when it’s time to make the decision and try not to sweat it too much until that time.
Is your 3 Questions podcast still something that’s going to continue on?
Yes. In fact, we’re coming up on our hundredth episode. We’re probably going to do some kind of clip show, and they’ve been asking me like, “What are your favorite clips?” I’m like, “I don’t know.” It’s like, I talk to people for probably 150 hours, somebody else tell me which ones were the best.
How have things changed for you with your relationship to the podcast during the pandemic?
Well, it’s yet another thing to do at home on the computer. [Laughs] There’s more of a connection when you’re in the studio with somebody talking about this stuff. Over the computer, it’s nice, it’s convenient, people do feel safe and you can’t… I mean, it’s not like my podcast is attempting to get people to spill their guts about stuff they don’t want to spill their guts about, but it is a podcast that begs a little bit of introspection from its guests. Being at home can kind of help that, but it can also, with the computer, be yet another line of defense to keep things on a surface level. I mean the point of the podcast isn’t just… Like I say, it’s introspection and self-reflection. I like it best when somebody says, “Oh gosh, I never really considered that that thing happening to me is possibly why I’m like this.” That’s just a very magical little process there that I enjoy in my own life, and I enjoy when I’m there when people do it.
I mean, it’s a needed thing. Think there’s so much access to everyone who creates anything, celebrities on social media and everything, but it’s always surface.
Yeah.
So getting to actually dig in a little bit deeper into things… Which is something I’ve enjoyed about the format change on Conan, as well. It’s not a five-minute anecdote and let’s go play flip cup. It’s a much more informative vibe if you’re looking to get to know the whole story behind certain things.
There is a similarity, the longer interviews on Conan do allow people… And by people, I mean, all the people involved, because when Conan had to break everything up into four to six-minute chunks, he was always looking for a laugh line because he knows that he’s got to throw to commercial. So it made it difficult for him to be inside a conversation. Whereas now we can go as long as we want, it gets edited and it does allow people to take more time, for him to take more time, for him to follow tangents and for the conversation to take on a life of its own. And the people having the conversation stop thinking about having the conversation and just start having the conversation.
It feels like Conan specifically had been aching for that kind of experience for a while with Serious Jibber Jabber and now his podcast (Conan O’Brien Needs A Friend). Is it possible that we wouldn’t be seeing this kind of format change if not for those podcasts (and web series) because it gives him an outlet for that kind of conversation?
Probably. I mean, that’d be a question for Conan, but I would say, yeah. I mean if I were a detective, I would say that’s a pretty strong connection there. The things all happened concurrently, so I think, yeah, that’s probably a pretty good bet. But there’s also just a natural evolution of things in that having done the same kind of show for so long, and it always being… I mean, we desire short, punchy things. I mean, television has evolved to be this very short, punchy thing. But then outside television, in terms of interview things, there are all kinds of long, meandering, organic things happening. I know Conan was tired of having six-minute conversations and having to chop things off in the middle. And he likes to talk to people. It’s one of his favorite things, so he’s getting to do it in, as I said, a more authentic way now.
What have these last few weeks been like with the official rundown of the show?
I think there was so much stuff to do. A lot of great old friends have come by to visit. And it was only last night because we’re taping the shows the night before, so we taped tonight’s show last night, and a couple of the talent executives were like, “How sad are we? What level are we? Like 1 to 10, how sad are we?” We all know it’s coming. We all know that the melancholy is coming because we’ve never had… I guess between The Tonight Show and the TBS show, there was not knowing what was going to happen, but we knew pretty much that Conan would get a talk show on another network. Whereas now going into the HBO Max thing and talking about different kinds of formats that might happen, it’s all so nebulous, that there’s a lot of people there that have worked there for going on 30 years. I mean, people like our stage manager started as a PA. He started out just running errands and now he’s our stage manager, and he’s been there the entire time.
People throw, “We’re like a family,” around and it’s usually bullshit, but there are people on that show that I feel are like a cousin or something, like really, seriously. They’ve been in my life for so long and a bunch of us play golf together and hang out together, and we’ve done different social things together. It’s certainly more than a coworker with a lot of people there. So yeah, it’s weird. A lot of the people there too, they worked for Conan and they were in New York. And when Conan came out to do The Tonight Show, they moved to LA so they’re in LA because of Conan. And by Conan, I mean the show more so than the person. But so, yeah, it’s dozens of people who are having a chapter change in their life.
How much do you look back on the actual on-air product that you guys have done and the bits, not just the camaraderie and the things that nobody sees?
Well, I mean, in an instance like this time, it matters a lot. Bill Hader was on the show and we taped it, and he mentioned finding us in high school. Like going over to a friend’s house and his friend was taping the show on VHS, and they would watch it in the afternoons. And Bill was like, “It was my first show that was mine,” and he said, “The first show that my parents didn’t understand,” and that’s really something. That’s like if you’re a baseball player, that’s like young baseball players telling you, “I looked up to you and the team that you were on, and that’s the kind of baseball I wanted to play.”
That’s what this is. It’s like, people like me, who had the same sort of professional or artistic aspirations, seeing this thing that I’m a part of, and it imprinting on them, the way that they wanted to then lead their professional, artistic life. That’s pretty significant. In terms of just having your work appreciated, that’s pretty great. Because I mean, I know money’s generated by it and stuff, but it’s all pretty silly. We’re not curing cancer. We are doing something important and making people laugh, and that is about as direct an expression of happiness as you get to, but it is still kinda silliness.
It’s amazing. I remember during the pandemic I did a thing on this one-off episode of the CBS 12:30 show that Adam Pally and Ben Schwartz did. And there was like a 10-minute section of the conversation with them where we started just talking about you guys and how much we worshiped you guys, both of you guys. Again, it was like kids talking about their favorite baseball player. It’s amazing the impact that you guys have had.
Yeah, and it’s weird. I mean, I don’t live inside my career and inside showbiz. I live in my house with my dog and my kids, and phone calls from my sister about my mom, and I just live in my life. So all of this stuff, it’s slightly overwhelming. Like, I don’t quite know what to do with it all. Except to feel proud and everything. It’s like some of the best people in comedy right now are spending some time saying how influential that our show, and then by proxy, me, has been. And like I say, I just have to think, “Gosh, that’s nice,” and then I don’t know what else to do with it [Laughs]. So I put it aside and maybe I’ll think about it in 20 years or something.
It must feel like you’re at your own wake to a certain extent.
Yeah, it is like that. The first time when I left the Conan show in 2000 to come out here and try my hand at sitcoms, there was a big sendoff for me, and it made me so nervous to the point of having to take anti-anxiety pills because I felt enraged just by the attention. Because it’s not my thing. I’m the sidekick for a reason. You know? [Laughs] I’m not the host because that’s just not the way I’m built, and I don’t want that. And so it was just a really weird thing when I felt like I was the bride at the wedding and the wedding just kept going on, and on, and on. It was too much for me. It’s not my thing. I just feel like, go look at somebody else for a little while, leave me alone. It’s much lessened now, and it’s not just about me. Yeah, but it is like these periods of being the topic of the conversation, especially in a meta way. Like, “Let’s look at what you mean not just right now, but in the scope of things.” It’s like, “Oh, why do we have to?”
This show still means something to people that are younger. I’m in my 30s, it means something to me and to people that are in their 20s. It means something to people that are teenagers. I’ll give you my five-cent wisdom: I think the reason for that is the versatility of the show and the ability to morph and be different things for different eras. What’s the secret sauce of the show’s enduring appeal?
Well, I think it’s because we never… I mean, there might have been some sort of overarching philosophy at different points, but to me, it always just felt like “let’s fill those [guest and comedy] slots with the funniest things that we can find.” It was always just in the pursuit of the well-built component of the show, then making a well-built show. And that’s all just based on sense of humor and taste. And that is something where, one of my biggest contributions to the show is that I am kind of the consigliere during rehearsal, and people who come to rehearsal can see this. Sometimes the writers don’t like me very much because I can be not exactly political. I mean, not rude, but if there’s a bit that I don’t think works…
Direct, you can be direct.
Yeah, I’m direct because I’ve been through it. I’ve been rejected and it’s like, if somebody doesn’t like a bit you wrote, it doesn’t mean you’re a bad person. You’ve just got to be like, “Alright, it’s not going to work.” And it’s all subjective anyway, there’s somebody in charge or a couple of people in charge, and you have to live by their rules because otherwise, you’re going to spend all day arguing about, “No, this is funny.” You just need somebody in charge to go, “Yes, no, yes, no.”
Conan and I are the yes, no, at this point. And our head writer, Matt O’Brien too, but it’s really Conan and I that are the last step of the quality control process before it goes out the door. And a lot of times he’ll just say to me, “What do you think?” And I’ll go, “Eh,” and he’ll go, “Yeah, eh.” And that’s just, in that little process right there, and this is where I will toot my own horn, which is a very non-Midwestern thing to do. That process right there is why our show is still funny. Because I think Conan and I still are excellent producers of television comedy, and we still can sort through the ideas and make it good.
There’s a version of this show in an alternate universe or whatever, that is still doing the masturbating bear and everything. And that’s the era that I grew up with, and I love that era. But it’s very interesting how you get from George Wendt and John Goodman leg wrestling in the first episode to where Conan’s going to Haiti or you guys are doing longer form interviews. How has that happened? Because there are a lot of people that don’t evolve in terms of what they find funny and you guys have.
I don’t know, I guess we did it right. [Laughs] You know what I mean? For me personally, my sense of humor… I have been on Twitter for whatever, 10 or 12 years, and aside from an ability to talk about current events and talk about serious things now and then, Twitter is a joke writers’ club that I go hang out at, and I have a bunch of joke writer friends. So I am in some kind of mainstream of weirdo joke writing.
It’s also kind of learning the evolution of the zeitgeist of comedy, where it’s “that’s not funny anymore.” And simple things that old people bitch about all the time, but like, “no, you can’t use that word anymore.” I get it, you used to use the word and you used it thoughtlessly. And I mean, you pick the word, I don’t even mean necessarily the most evil words. I mean, just lots of words. And you just learn like, “Oh, that’s hurting somebody. Oh, okay, I can use another word.” Or “making this kind of joke is hurtful to people and I’ve made them before, but okay, well, I can make other kinds of jokes.” I just think that he and I never stopped thinking like, “Well, I can compete in the marketplace of funny ideas, and I want to stay in touch with it and I want to stay current with it.” There are a lot of people that I think, don’t. But I also think a lot of those people are scared that they’re going to run out of ideas, and that’s never been anything that has plagued us. It’s always like, “Well, we’ll always have something… We’re wise asses that always have something funny to say about something.”
And we’re funny people to be around. There are a lot of comedians that aren’t that funny to be around. They’re funny on stage and they think of really great stuff, but they’re just not that interested in being funny, whereas Conan and I are trying to entertain people all the time. Not all the time, but pretty much all the time. If you come hang out at our show, and people will say this, interns and stuff, it’s a fun place. We’re trying to have fun and make each other laugh, and I don’t know, that’s just something that we’ve held onto. And I do know that that’s something that some people stopped doing. They don’t enjoy it anymore, and it’s just kind of… We still want to crack up and giggle in church, just still want to be the ones that are whispering jokes to each other in the corner and making each other laugh.
I think there are people that get precious about, “No, this is who I am. The funny comes to me, I don’t go to the funny,” I think you guys go to the funny, is that maybe accurate?
Absolutely, absolutely. And also too, there is a very destructive phenomenon that occurs and it is not being told no for years and years and years. You get to a certain level of fame and money and achievement, and people just start to cater to you, and you don’t really get a lot of pushback on things. We never really… It starts with Conan, you’ve seen the things with Conan and his assistant. He has surrounded himself with people that take the piss out of him. If he ever gets too puffed up, he is surrounded by people that he has given pins to, who will pop his balloon. It’s an incredibly healthy way to live and an incredibly healthy way to exist, especially in this fucking weird world of showbiz, but especially talk shows where if you are a talk show host, you have agreed to basically hand over your personality to become a product, that is then packaged up in 16 different ways and sent out every day. It can make you weird and it can make you crazy, and I think there are lots of examples that anyone could easily come up with without thinking too hard. He has never done that. He’s had me to make fun of him. He’s had Sona to make fun of him. He’s had writers to make fun of him. And he gets his licks in too.
(@rrrubenciito) 
