Welcome to our column Sketch Anatomy, where we ask some of our favorite television writers to choose any sketch — one they personally wrote or one from history they find particularly hilarious, notable, or underappreciated — to learn from a writer's perspective what separates a successful sketch from the rest.
Every longtime Conan O'Brien fan knows the work of Brian Stack, who joined the Late Night writing staff in 1997 and helped define Conan as the unpredictable oddball of the late night talk show circuit for the last 20 years. Stack has shown up on 30 Rock, The Office, Parks and Recreation, and elsewhere, but he's best known for playing a host of bit characters opposite O'Brien, from The Interrupter to Artie Kendall the Ghost Crooner to part of the three-man act The Slipnutz alongside writers Jon Glaser and Andy Blitz. For this week's installment of Sketch Anatomy, we spoke with Stack about the origin of his character Hannigan, the persistent old-timey traveling salesman he played on Late Night with Conan O'Brien, as well as how he broke into television writing, how the Traveling Salesman bits evolved, and his thoughts on late night's evolution over the last two decades.
How did you first get involved with Late Night?
I kind of fell into comedy writing through improv and sketch comedy first in Madison, Wisconsin at the ARK Theatre and then in Chicago with ImprovOlympic and Jazz Freddy. Then later, my first professional job in comedy was working at Second City in Chicago — I was in the touring company for two years and then in the E.T.C. resident company for a couple years before getting the job at Late Night, which came up in kind of a strange way, actually. One of the Conan writers Tommy Blacha — who is one of the funniest people I've ever met in my life — broke his leg really badly and couldn't even come into work, so they wanted to bring someone to fill in for a few months, and I was recommended to Conan and the then-head writer Jonathan Groff by some other writers at the show who knew me, including Tommy and Brian McCann and Andy [Richter] and Greg Cohen. I sent in a packet of ideas not thinking I'd get the job, but luckily they liked it enough to bring me on. Then, luckily, they liked the stuff I was doing and decided to hang onto me even after Tommy came back. So it was supposed to be a 13-week job and it turned into…I've been there for over 17 years now. [laughs] It's really strange.
What was your first experience performing on camera on Late Night?
I think one of the writers asked me to play a doctor who came in at one point. I don't even think I said anything. I think one of the first characters I did on the show was a very silly character called Bathtime Bob the Hygiene Cowboy who came in to sing about bath time, but like many of my characters he had a very dark, tragic underbelly to his upbeat nature. [laughs] That actually had been a character I had done a little bit at Second City, but it never ended up in one of the shows — it was just a character we goofed around with. I did the occasional "Clutch Cargo" voice where they'd show the lips. Robert Smigel did about 90% of those, but they'd have me and McCann do them occasionally and Louis C.K. did some — even when he wasn't writing at the show anymore they'd bring him in to do Mike Tyson once in a while. It's funny, I remember Louis coming around when he was making his little short films, and I remember him stepping into my office and saying "Can I borrow this lamp?" [laughs] I think he was kind of working with what he had, but he was always one of my favorite comedians, even long before he got really famous.
What's the origin story of Hannigan, your traveling salesman character?
I think it was Andrew Weinberg who suggested that I play an old-timey salesman, and then I wrote the sketches with Andrew and Michael Koman, who both went on to create Eagleheart with Chris Elliott, which I love. It started off with me trying to sell Conan vacuums and actual appliances and things like that, and then I would veer into selling terrible jokes that no one would ever want. But as we wrote the sketches it evolved — I think by the second time we did it — into me selling all kinds of products that no one would want and veering from not just jokes but into sketches, like occasionally I'd pitch a horrible sketch idea to Conan. Like a lot of my characters, it evolved into having a darker and darker… [laughs] background and a very troubled personal life. So it evolved into what it became pretty quickly, but originally I know it was Andrew who was like "How about if Stack plays an old-timey joke salesman who sells terrible jokes?" In the back of my head I always had that old-timey voice like from those William Powell Thin Man movies, I think that's where the voice came from. But yeah, Andrew, Michael and I wrote those sketches together but I think it was originally Andrew's idea.
The way it evolved reminds me of SNL's "Celebrity Jeopardy," where a sketch starts as one idea then becomes something you couldn't have first planned. It seems like a lot of great sketches have that "accidental" element to them.
Absolutely. A lot of my favorite ideas and things that developed particularly at Late Night were often very accidental, like we kind of stumble onto something like Oh! I like that angle! A lot of our favorite bits on Late Night, like the Bulletproof Legs Guy and the Slipnutz, were almost all complete accidents from being there too late and being sleep deprived. [laughs] But sometimes something would just take a turn, even in rehearsal, and we'd be like Hey, I like the way that's going even though that was an accident — let's go more in that direction. That just happened with WikiBear on our new show. Originally WikiBear was going to be providing inaccurate facts with enthusiasm and confidence, but then during rehearsal we took this dark turn into talking about the Manson Family and Conan was just like "Hey, I think that's where this should go."
There's a lot of old-timeyness between the Traveling Salesman and the Ghost Crooner. You mentioned William Powell — were there other influences you had growing up that helped shape those characters?
Yeah, my love of old movies like the Thin Man movies or My Man Godfrey — all those old screwball comedies from the '30s. I think the Crooner developed when I realized one day that wow, Rockefeller Center's been here since the 1930s, so there were old-time crooners here like Bing Crosby with those old fashioned microphones in this same studio. On the radio Bing Crosby sort of had a dark side, and I remember being very intrigued by that because you saw no trace of it in his friendly onscreen persona. So it started to fascinate me how if someone sang like that with this really inappropriate racist or misogynist thing underneath all that. And also I had seen this technique used in another sketch where you could fade something out by using a locked off camera shot to make it look like it was half there, like a ghostly image. I didn't know it was that easy to do, so once I saw it done for some other bit I realized I could stand there and look like a ghost who was kind of halfway there. So that's how that developed — just from thinking about the old crooners who sang in 30 Rock.
A lot of your characters — the Traveling Salesman, the Ghost Crooner, and obviously The Interrupter — were known for showing up unannounced, which is something that made Late Night so unique. And you had to make those characters fully formed in just a few minutes, whereas on a sketch show you'd have more time to flesh them out.
Yeah, we oftentimes had to fill time — we used to call them Act IIIs because there was some kind of sketch or silly thing that would happen in between the first two guests, and I always enjoyed Act IIIs the most because you could fill them in with something kind of conceptual or weird or like you said, something that interrupts the show. The Interrupter actually developed because Conan was often joking with the writers about "Okay, how are you guys gonna interrupt me today? What kind of characters are going to interrupt me?" [laughs] And so Michael Koman said "Why don't we just have a character called The Interrupter where that's his sole purpose?" Michael and I wrote those sketches together, and again, the backstory of the character evolved as we wrote the bits. It was originally kind of a comment on the fact that we would interrupt Conan so much with silliness. And you're right about having a limited amount of time. It had to be something relatively short, usually three or four minutes tops in between guests, because we only had a certain amount of time to do anything in the middle of the show like that. So they were usually quick slices of silliness.
How did you write the Traveling Salesman bits?
We'd usually just start off with okay, he's gonna sell two or three horrible things no one would want, and then we would brainstorm on those, and then usually by the third or fourth thing he would get into the jokes or sketches. Like he'd be selling products that no one would ever buy. So we'd have a lot of fun brainstorming on those, like Doc Self-Destructy's Tranquility Tablets which would basically be poison you'd use to kill yourself. It was always Doc-something, or the companies always had "-co" at the end so it'd be like "From Racistco!" or something, so he'd have a barrage of companies that were just horrible.
And he always offered the more upscale joke from Jokeco followed by a joke from a more affordable "pedestrian" line.
[laughs] Yeah exactly, so even the terrible jokes had a hierarchy. I always really enjoyed punching the card away at the end and saying things like "Cash or credit?" as if it was just a given he was going to buy them because they were such great jokes, but they were obviously horrible. It was always really fun. You know, as a comedy writer you spend so much time agonizing over trying to make stuff funny, so it's really fun to write deliberately bad material… [laughs] …where you can just relax and go okay, let's make this stuff as bad as humanly possible.
How long did it typically take you, Weinberg, and Koman to write each Traveling Salesman bit?
Usually we'd write them the night before, because as with shows like SNL, you kind of have the one night to write everything. We would sometimes make changes during rehearsal, and Conan, being a brilliant writer, would have a suggestion for a way to improve a joke or maybe take something out to improve the pacing. Sometimes he would leave things exactly as written, and other times he'd have really great ideas for trims we could do or additional things we could throw in there. The majority of our sketches at Late Night, Tonight Show, and our current show tend to be written the night before and the day of, so you work on it the night before and you might come in in the morning and do a little bit of a rewrite. Sometimes we'd write everything the day of because the idea would come up in the morning and you'd say "I got an idea for something maybe we could try today." A lot of that reminded me of working at Second City, where you could have an idea on the way over and throw it up that night in front of people, which is a wonderful way to work because there's not a lot of wardrobe and sets to build — you can just kind of throw something out there and see how it goes.
Do you have any favorite jokes in particular from the Salesman bits, whether it's a company or product or even hint of his backstory?
One of my favorite jokes — I have to give Michael and Andrew most of the credit for this one — but he said "I can get you the Stones!" and Conan said "The Rolling Stones?" and he said "No, Morty and Isaac Stone — two grizzled old railroad attendants I met in a Catskills VA hospital. Morty claims to play the saw, and Isaac screams when he sees a flat surface." I don't know why that made me laugh so hard. I always loved the other joke, I think it might have been Michael's, but one time the Salesman looked up to the sky and said "Hooked another fish, Pops. Watch me reel 'em in." And Conan said "Who are you talking to?" and he said "My late salesman father. Killed in his sleep by a shifty Creole prostitute. But back to the jokes!" Just the idea that he's talking to his late father who had just as pathetic as a life as he does.
I love the way he introduced the jokes he was selling: "Hop on the Giggle Trolley, we're off to Laughs Francisco!"
One I remember was "Put on your turban, we're off to Laughganistan!" It's just ridiculous and offensive. Or "Grab a Sherpa, we're climbing Mount St. Funny!" They were always just terrible. There's something about the persistence and enthusiasm he had for these things that nobody had any right to be enthusiastic about. [laughs] Because we've all had salesmen come up pitching their stuff with great enthusiasm that you know would just be a disaster if you bought it, but that's their job and they're damn well gonna get out there and tell you it's gonna make your life better.
When I interviewed Jeff Loveness from Jimmy Kimmel Live, he said you had "such a sadness to each character, but they would not acknowledge their sadness." Is that a fair assessment?
Yeah, that's very true. But I only noticed that after looking back at a lot of them. [laughs]
So you weren't conscious of that at the time as a specific approach?
I don't think I was conscious of it, but it makes sense in the way that Stephen King said he would write books that scared himself. Maybe these characters were a way for me to — without even realizing it — deal with the kind of insecurity and self-loathing that most comedians experience, but dealing with it in the comedic abstract way where you find a way to laugh at those things that most comedians experience, even if some of them are better at hiding it than others.
Do you think that kind of sadness/honesty helps make a sketch or bit more timeless? It seems like tragically funny characters keep their staying power better than those without that sad underbelly.
I think so. A lot of the comedy that has really stayed with me over the years, whether it's Cheers or Party Down or Freaks and Geeks or movies like Billy Wilder's The Apartment, there's often an undercurrent of sadness beneath the comedy. I remember the episode of Taxi when Alex's dog was dying, and as a dog lover that episode always stayed with me because they didn't play it for laughs. It was a very funny episode, but they let that moment of him just being genuinely heartbroken about losing his dog — they just let that play very real. Or you watch The Office and Steve Carell's character was often so heartbreaking, you know? And he played it with such humanity — he was obviously doing his best to push through, and being a genius actor he was able to show in his eyes often that he was just devastated by something but trying to remain the smiling boss. The movie Grosse Pointe Blank has a mixture of funny and sad, and I think those are oftentimes the movies and shows I go back to. They seem to capture that contradiction in life.
Considering you've been a writer for Conan for almost 20 years, what do you think of how the late night world has evolved and where it's headed?
To be honest, over the years I thought there'd be a little more diversity in it by now. There still tends to be a lot of funny white guys hosting the shows, and a lot of them are really great, but… [laughs] I think also that you do tend to see different kinds of shows with cable now with stuff like IFC and Comedy Central. You see more different kinds of late night shows, and some of them obviously reflect social media really strongly, like @midnight with Chris Hardwick is something I couldn't ever imagine happening 18 years ago. So it's evolving as social media and things like that evolve. I think the bottom line of having celebrities coming by to promote whatever they're promoting and trying to intersperse that with comedy seems to be a constant that I don't see going away — anytime soon, anyway.
My favorite kind of comedy on late night has always been the non-topical silly stuff where it's not really at anybody's expense. My least favorite kind of joke is a celebrity joke, because it tends to be very familiar or sometimes very mean, and if it's not mean it doesn't even work, usually. [laughs] But that's just part of the landscape, and some people definitely have it coming. But my favorite kind of comedy on late night is at no one's expense but the character that's involved in the sketch where you're not really going after anybody. There may be less emphasis on silly character bits than there used to be in general, but we still do it occasionally, and you'll see some wonderful silliness on Colbert or Seth Meyers's show that tells me it'll never really go away completely; there's still an appetite among comedy writers and fans to see some of that. And I'm very grateful for that, because that's always been my favorite.