Every week, host Adam Sockel interviews a popular member of the literary world about their passions beyond what they're known for. These longform, relaxed conversations show listeners a new side of some of their favorite content creators as well as provide insight into the things that inspire their work.
Sidney Karger is an award-winning screenwriter for film and television with credits including Billy on the Street, Comedy Central, and Saturday Night Live. Growing up near Chicago, he was raised on a steady diet of improv and sketch comedy from some of the greats of Second City and Upright Citizens Brigade. It's a shared love Adam also adores. They also get into his incredible new romantic comedy Best Men!
You’re listening to Passions & Prologues, a literary podcast where each week, I interview an author about a thing they love and how it inspires their work.
I'm your host Adam Sockel, and today's guest is Sydney Karger, who is the author of the new romantic comedy, Best Men. It is honestly a perfect summer read, I am actually just finishing it up right now. I’m really, really loving it.
It is a classic boy meets boy where one of the boys is the man of honor in a wedding, and the other one is the best man. And they have an awkward encounter before they officially become part of this wedding party.
And they have to work together to make things happen in the wedding itself, while also having their own enemies to lovers/friends. It's just so well-written and the reason it is so well-written is that Sidney, today's guest is a screenwriter and a comedy writer by trade.
And in this discussion, we talk about his origins in comedy, and we take a nerdy little sketch comedy, improv comedy, deep dive into his background. And this is something that I actually happen to be passionate about as well.
And it comes through, I'm sure in the conversation where we discuss different things like the Upright Citizens Brigade and Second City and Saturday Night Live, and just a whole host of these little pockets of comedy where some of the biggest names you know in comedy all come from before they become the biggest names in comedy.
Just a lovely conversation, I think you're truly going to adore it and I think you're going to love his book Best Men as well. Again, it's a perfect summer romantic comedy.
And if you're looking for another book recommendation along those same lines, it is June, it is pride month. I'm going to be offering up as many pride-related book recommendations as I can throughout the month and beyond, of course.
And another one that I just read recently is, Is It Hot In Here? by Zach Zimmerman and this ties together because Zach is also a comedy writer and comedian. And this is a book that is a collection of essays and lists and musings, all about his New York-based comedy life.
It's really, really funny. It talks about different things like his experiences with his very, very meat-eating Southern family and how it was like coming out to them, and all of these different things about religion and Tinder dates gone horribly wrong, and all sorts of just really funny quick memoir essays. If you're a fan of like David Sedaris, I think you will really, really love, Is It Hot In Here? by Zach Zimmerman.
And as always, you can reach out to me at [email protected]. I say this every week, but I love hearing your passions, the things that you guys are crazy interested in. I was just reading a couple of those emails over the weekend, and as always, I at the beginning of every month, send a random bookshop.org gift card to one of the people who sends me one of those emails.
And I haven't asked in a few weeks, but if you have a moment, if you could leave me a five-star review or a rating wherever you listen to your podcast, it helps people find me just a little bit more easily. And last things last, you can find me on TikTok and Instagram, Passions & Prologues. That's where I'm doing book recommendations and just bookish thoughts all over the place.
So, that is all the housekeeping, I'm not going to keep you here anymore. I am so excited for you all to hear this conversation with Sidney Karger, author of the now available, Best Men on Passions & Prologues.
Sidney, what is something you are super passionate about that we’re going to be discussing today?
So, I am super passionate about oral surgery.
Oh, this might be the most …
I was like, I guess we'll go with it.
I wish, no I'm going to say comedy.
Okay, we can play in that space a little bit more easily, I think.
That's the real answer.
So, for people who may not know, you are in addition to being an author, and we'll get to your book in just a little bit – but you're also a screenwriter, so let's do lots of comedy podcasts and start from the beginning.
What was your first introduction to the world of comedy and what route was it? Was it standup? Was it sketch? Was it TV shows? Where did you discover this?
So, I feel like it's a passion of mine just because it's sort of permeated every aspect of every point of my life. And it's something I love and it's something I seek out, and it's something I'm constantly doing in my work and outside of my work.
So, I guess it comes from — I grew up in the suburbs of Chicago and I was in the northern suburbs, and my parents would take us to the city every once in a while, for an urban outing because we were in this city. And so, every once in a while, I would have our special Sunday in the city, and we would always end up in a neighborhood called Old Town.
And Old Town is in the shadow of Second City, and we would always walk by Second City and my parents would talk about it. And by the way, my parents were also super funny, and my dad was always telling elaborate jokes that he could never remember and the butcher.
And my mom was doing impressions which I didn't realize at the time, like she's sort of an impressionist. But as I grew up and was able to find out, I'm like she's an imprint, she imitates people. And I'm the baby of four older siblings. And so, I was kind of grown up with adult humor and my next sibling is almost 10 years older than me. So, it was all very sort of adult, and I was trying to — and they all have great sense of humor and so I kind of learned from the best.
But then just growing up in the shadow of Second City, I eventually — when I became older and I think it was in high school, my parents finally took me there and it was this magical wonderland. And live theater was the same way for me too, just being in … I think I saw like The Wiz when I was a kid. I was like the first musical theater as a kid.
And I remember being in Second City and one of the people — it was partly improv, but it was also scripted, like the night of scripted. And then they were doing improv and they held on my mom at one point and they said she looked like Olympia Dukakis. And we died laughing and it was like this is just a great way to connect with my parents and my family.
And so, I would then beg them to take me there all the time when I couldn't drive. And then when I went to college, we would go there with my friends. Just hang out at Second City and I was obsessed growing up with all things comedy.
I love this so much, so I'm also a very big comedy nerd. I love listening to podcasts and interviews with people who either came from Second City or obviously, like older Saturday Night Live. You know, writers and actors are all arranged now, there's a bunch of different shows, like Fly on the Wall with David Spade and Dana Carvey.
There's all these different very popular shows these people who are talking about these things. But I have always found myself being so deeply blown away by improv comedy, especially any version of comedy I think is incredible. Like you were talking about, I think it's a very unique skill that can be learned, but a lot of it is innate in making other people laugh.
But when I watch people like Ben Schwartz I think is the fastest person I've ever heard. Every conversation he has, he seems to just ... it's like he knows what is coming and it's not, it's improv. So, that for me, I love standup, I love sketch, but improv is the thing that if it's done well, to me, is always the most impressive.
And so, what was it for you about going to Second City and experiencing these shows that had you catch the bug, I suppose?
I think it was sort of the — it's weird because I'm not a team player, I'm not into team sports. I like tennis and skiing, and swimming, those are my solo sports. So, I can't say it's like the group thing, but I guess I was the same way.
I was drawn to improv and sketch, and I loved standup comedy, but I guess I was always sort of like a wannabe performer in a way. And I felt like when you're in an improv group, which I eventually did, you can kind of get lost and hide behind your fellow people and you can kind of come out and land a joke and kill.
But I would watch standup comedy and I would worship any kind of standup on TV, and back then it felt like there were more Friday night standup comedy shows. Just seeing them on stage, I could never do that because you're alone and it's super personal and you're talking about your demons and making it funny, where like sketch and improv, you can hide behind characters and impressions and make up worlds.
And I started doing improv in Chicago like training. There still is a theater called the Annoyance Theater, and it was like an offshoot of Second City. And I think I just graduated college and it was the cool version of Second City and I'm like, “I'm going to do the underground version.” And it was people from Second City who started it, like Mick Napier and all these greats.
And I did it for a while, but it was again, sort of like I was more of a writer than a … I wanted to perform, but I was such a shy kid and so reserved that every time I had to go on stage, it would eat me up.
And I have so much anxiety and I couldn't get through it. But it was fun because when I could actually finally get on stage and do something funny and then hear the laughter, that was the thing that kept me going. But the stage fright eventually was my downfall.
Yeah, it won over eventually. So, how did this joy of comedy and passion for it, like you said, this love of taking these classes and being a part of it, how did it go from an interest to a career for you?
So, I mean, I guess well also, I was obsessed growing up like a lot of kids with Saturday Night Live, and weirdly, my grandmother lived in the Upper Peninsula of Michigan or whatever, I guess it was closer to Canada and we were able to see SCTV, which is like Eugene Levy and Camembert.
I remember sitting in front of a glowing television in the dark at 10 o'clock at night when I was a kid watching this stuff and soaking it up, and I soaked up Saturday Night Live and it was always sort of a dream to get there.
And also, in the suburbs where I'm from, I was obsessed with movies and John Hughes was shooting all of his headshot, all of his movies where I'm from and Breakfast Club, 16 Candles. And it was like, “Oh, my friends,” that was where the party scene that this girl I went to high school with was shot, like watching them, you're like, “Oh, that's where the Porsche dealership is or whatever it is.”
And so, I was obsessed with those, and I knew from an early age that I wanted to be, because I could not stand on stage and be exposed to people. I think I'm like, “Get me behind the scenes, I'll be a writer.” And so, I knew I wanted to write in some capacity from an early age. And I ended up — I was trying to emulate John Hughes's trajectory when he started out as an advertising copywriter.
And he worked at, I think Leo Burnett in Chicago, and then he became a filmmaker, and I was like, “Okay, I'll follow that.” Even though there was film schools and stuff like that, it just didn't seem like you could go to film school and then become a filmmaker. It just felt like if you go to homeschool and I don't know anyone who did that. So, I couldn’t figure that out.
So, I ended up going into advertising as a major in college, weirdly knowing what I wanted to do, like advertising is a steppingstone to Hollywood. And then when I graduated, I got jobs working as a copywriter in Chicago, and I was doing the improv thing and writing screenplays. And then I moved to New York with a job as a copywriter.
And then it was right around the time when Upright Citizens Brigade Theater had started and Amy Poehler with the other three guys started this theater. So, I started doing that and so that was kind of fulfilling my comedy need while I was an advertising copywriter.
And then I was writing short films and directing them, and I took all my experience and there was sort of like two goals living in New York. One was Comedy Central and Saturday Night Live, and like Comedy Central at the time had like John Stewart Daily Show and South Park.
And so, it was like the pinnacle of comedy to me, and it had the word “comedy” in it, so I'm like, that's where I need to go. And I eventually, took my experience and was able to get a job. I'm making it seem way easier than it was.
No, but I love what you're saying. First off, I feel like you have hit like my pantheon of the things like my comedy, like you mentioned SCTV, Upright Citizens Brigade, like literally the people that I adore, like John Candy, Rick Moranis, like Matt Walsh.
You've named like literally all these different … Amy Poehler, like Nick Offerman, all these different places where all of my comedy heroes have come from, you have now named every single one of them. But I'm wondering if you can … because you were just jokingly saying like you're making it sound like it's easy and obviously, it's not.
But something that I have always found interesting about comedy and writing in general, really as an aspiring author myself, like I think the thing that I love about writing, whether it's comedy or literary fiction or romance or whatever it is, is like there's no one stopping you from putting pen to paper, I guess, fingers to keyboard at this point and trying to create something.
And so, you mentioned it wasn't easy, but I'm curious, so like from an inside baseball standpoint, because I’m, like I said, a comedy nerd, I'm a writing nerd. What was the process like for you to go from having a copywriting job to, was it like submitting packets? I guess what was the process like for you to get in front of, like you said, Saturday Night Live and Comedy Central and these titans of comedy?
Yeah, I mean, it's funny you mentioned the greats because I didn't realize, like in those high school and college years, we were seeing the greats perform. And it dawned on me years later, I was like, “Oh my God, that was Chris Farley who took off his pants.”
Not to cut you off when you mentioned, I was like, okay, I could fall down a rabbit hole where I just spent 20 minutes asking Sidney which Second City people he saw. But please, if you want to do a list, I would love that. But please, if you want to do a list, I would love that.
Well, I mean, it was Chris Farley, which I couldn't believe. I think I caught the tail end of … or he was like a special guest or something. And then when Tina Fey got on Saturday Night Live Weekend Update, I was like, “Oh my God, that's the woman …” I would see her because I recognized her face.
And then Rachel Dratch was like star of every show we went to. She would just kill every show at every show. And it was just like … but you kind of don't know who they are until later. And then Amy Poehler, of course, when she started UCB, I remember when she got the Saturday Night Live job and everybody was sort of like, “Oh, she's moving on.” And it was like sort of a pivot.
I kind of, again, I remember going to lunch with a couple guys who became sort of semi-famous. And like we were getting a bagel. And I was like, “You guys want to be writers, right?” And they're like, “No, we want to be on Saturday Night Live and performing.” And I was like, “I think I'm in the wrong track.” Because I was the only one at the time …
I think after I left it became this sort of breeding ground for writer-performer multi hyphenates who did everything. But it didn't have that track when I was there. It formed later with like the Bobby Moynihans and Kristen Schaals and things like that.
But so, for me, so I was still sort of figuring it out at the time where I was like I need to figure out how to submit to the Colbert rapport. And then I found out because I stopped doing improv, I wasn't in the pool of people who knew everybody and was sort of like auditioning and doing writing packs.
So, I never really knew when those were coming down the pike, and I was in my Comedy Central bubble. And of course, at the same time I was equally passionate about screenwriting, and I was writing scripts and I ended up … I was writing spec scripts of movies that were original ideas.
And I ended up getting a film manager based on a screenplay. And that got me an agent and the script ended up on the Black List, which is like Hollywood's most liked screenplays of the year kind of thing.
And so, then I kind of got a little more into the bloodstream of things because I'd stopped doing the improv and I was getting sort of stuff sent to me through my agents that I would review. But I found out that there was this — it used to be called like the Fax List on the Saturday Night Live, where you're submitting jokes every week for a weekend update. And it became with email, like I guess the email list, I don't know.
It could have been just me or a hundred people who were doing this. Because I was offsite and while I was at Comedy Central, you had to audition to get the Weekend Update joke writing freelance and I was able to do that. And then I did that for three seasons while I was at Comedy Central, while I was writing my own screenplays on the side. So, I kind of had a taste of what I wanted when I was a kid, which was great.
And then the screenwriting kind of took off in a way that I couldn't avoid and kind of wanted to get my attention to. Again, it was the comedy of like had that had been sort of with me in my DNA from the early ages, like followed me into screenwriting too.
Yeah, yeah. So, I want to like nerdly deep dive into comedy with you the whole time, but I want to be also respectful of your time. So, like how does that transition from … like you said, screenwriting is a very different process from writing a novel.
And writing a novel is obviously much different from submitting like one-liners for weekend update and things like that. So, what was that transition like for you going from a screenwriter and focusing on that style of writing and then transitioning into what made you want to write a novel with your new book as we're recording this after the book came out, Best Men?
How did that transition come up to you? How did you decide I think I want to take a look at this avenue of writing now?
Yeah, I mean if you look at it on a graph, it makes complete sense. Because while I was at Comedy Central, I was writing and directing for other shows. So, like Amy Schumer and Sarah Silverman and Broad City, I'd write. All the writers there would write promos, which are these giant productions people sometimes don't realize. They would do like huge productions to promote the show with the talent.
So, I was always constantly writing in the voice of like a Sarah Silverman, which I felt like I could confidently do, just take your sort of impersonation skills, and put them into whatever talent you're writing for.
And along the way, I was developing my own voice and that's when the first screenplay kind of was getting a little bit of traction, I was able to like okay, I think this is my voice. It's not like broad, super broad comedy, but it's a little more maybe dramedy. And I kind of went back.
And also, being at Comedy Central for three years, I stopped watching comedy because I had to watch it for work. You just don't have the brain power to watch even more … and I would want to watch like the darkest, most disturbing documentaries, like the complete opposite while I was at Comedy Central. But I was also trying to channel it into my own work.
So, I kind of tried to find my voice in the screenwriting world and I was able to become a working screenwriter and left Comedy Central and was able to sort of sell screenplays and option them. And there're multiple things in development now, but I've taken a pause because of the writer strike.
But then during that time, I didn't really … I haven't mentioned this. But when I was a kid, I'd always wanted to write a book and I wrote like a choose your own adventure book when I was 12. It was terrible and it was like fan fiction.
And so, that was another thing, just any kind of writing I've wanted to do my whole life. So, I never really expressed it, and I was always like I'll probably have to be 75 by the time I get to writing a book because I'm so focused on screenwriting.
And out of nowhere, my film manager asked if I wanted to write a book, even though I hadn't really expressed that to him. And that's why having reps is great because they kind of pull these things out of you and they see you for whatever potential you might have.
And I was like, “Yes, of course, I want to write a book.” And so, I was introduced to my now book agent, and I had through the years ideas that I kind of pitched and formulated and put together, and then I was able to pitch and sell Best Men, which is the book that just came out.
Yeah. So, can you introduce my listeners to Best Men, and kind of where the idea came from and all that good stuff?
Sure. So, it's a romantic comedy and so, there is a comedy in it, which again, I wanted to do. And it's about a guy named Max Moody and he's a gay guy living in New York, and he's about to turn 35 and he is kind of like a hopeless romantic but doesn't want to admit it. And he kind of covets that little paragraph from the New York Times that announces you're getting married.
And so, he is thrown for a loop when his best friend announces she's getting married before him and wants him to be the man of honor in her wedding party. And so, he's kind of quietly spins out of control because he thought he'd get married first.
And then he meets the best man of the groom whose name is Chase. And Max and Chase are kind of polar opposites. And like Max is introverted and midwestern, and Chase is New England-y, very social, outgoing, and they can't stand each other at first and then they kind of like try to tolerate each other for the sake of the wedding.
And then it's sort of a will they or won't they get together romantic comedy. And yeah, it came out like a month ago.
So, how did it feel … like you said, you knew you guys wanted do this and your representatives sort of like you said, almost saw it. I love that you were saying like they kind of saw it in you before you saw it in you. Like, “Hey, you should do this.”
What was the experience like though writing in this style where like for people who might not be aware, like screenwriting is very different from the layout of a book in the things that you say versus show and then all these things. How did that process feel for you getting to like stretch out these characters and kind of build these relationships in a different way?
It was amazing because whenever I had sort of sat down through the years to kind of “work” on my book, like whatever that was, I would start typing and I'd be like, “Oh, this is going to take years.” Like I don't have time between Comedy Central and screenwriting and like I just never would make that block of time to write.
And screenwriting is very sort of economical compared to writing a novel. You have to make sure you're hitting the right beats structurally in a screenplay on certain pages, sort of. And you kind of know where you're going within 110 pages and usually, unless you're having a voiceover, it's sort of the on-mission voiceover that's very cold and like, “Andy walked down the street and kept walking down the street.” Whatever it is. So, it's very different.
When I started writing the novel, I just was like completely liberated and felt like my hands were just going typing without my brain. And it was a totally different muscle because you have so much more room for your canvas for the characters and the story. And I luckily have the sort of screenwriting structure foundation built into what I was doing.
So, I knew, again, the goalposts I needed to hit. But within that, I was able to have much more fun with character development and description and being inside the character's head too is a joy.
Yeah. Is this something that you plan on continuing moving forward or are you like … I know you mentioned the writer strikes. I'm sure you might have a little bit of time to work on your own stuff now, but who knows and how long that's going to last. But is novel writing something that you plan on pursuing moving forward as well?
Yeah, I love it. I am actually in the middle of edits on my second book which will come out next year. And I paused the screenwriting stuff because of this strike. But I have all these things sort of in development that I'm kind of, hopefully, the strike will end soon, and I can back too. So, I'd love to juggle both screenwriting and novels.
One last question about the writing process. Like for you, is that juggling … obviously writing is a very unique skill, but do you find yourself like needing to dedicate like large blocks of time for like novel writing versus screenwriting? Or are you able to kind of, I don't want to say multitask, but basically, are you able to kind of multitask different projects like that?
Yeah, you kind of have to be able to do that because I'm working with producers on the screenwriting side and then my editor and the publishing house on the book side. So, it's sort of lucky thing when you have a bunch of projects. If you're lucky to have them then, and you're also lucky then to have them be in certain different stages of development, then you can kind of.
So, it's not like you're writing the block of the screenplay and the block of the book. Hopefully, it matches up. So, it's sort of like you're revising the screenplay and then you're starting the book. Or you're starting the screenplay or you’re revising the book.
So, it's sort of, once I always kind of say that like when I finished the first book, I immediately wanted the sort of like cleansing of writing a screenplay. And then when I finished a new screenplay, I'm like, “I want to get back to a book.” It’s kind of fun to juggle those different parts of your brain that you're using and it's hard.
I think the blocks of time … I used to be able to sort of like, “Oh, I'm going to write in a cafe and it's going to be romantic and cool.” And like I can't. I need dead silence, nobody around. I'll walk the dog. I'm like I just need that sort of like space and time … for both of them, I need the space and time, yeah.
Yeah, that makes perfect sense. Okay, last question for you. I always end every conversation by having the authors who come on, give a recommendation. It can be of any kind, it can be a book, it could be a movie.
I've had people say like “Go for a walk,” I've had people recommend certain like recipes for pies. So, what is just something you want to recommend that you think more people should know about?
I got to get those pie recipes.
I will stick with the comedy theme and people were talking about it when it came out a TV show called Jury Duty and I feel like everybody talked about it immediately, and then we binged it, and now no one's talking about it. So, I'm going to push that out into the world again.
And it's on Freevee, it's sort of a mockumentary hybrid. It's scripted, but I don't want to give it away, but it's not scripted. And it has James Marsden as the star of it. And then the comedy writers who created are all like amazing and have done a lot of great things. It’s high-high. I binged it and couldn't stop.
It's incredible. I watched the first episode last night, weirdly, it's so good. And it's also, if you are a comedy nerd, it is a who's who of like character actors that you'll be like, “Oh my God, that person's from Parks and Rec.” You'll love it. Yeah. Oh man. Perfect.
It's hard to talk about without spoiling it, but it's a must-see.
Yeah. I highly, highly agree. This was so much fun, Sidney. The book is so wonderful, and I loved this conversation.
Thank you for joining me today.
Thank you so much. That was super fun.
Passions & Prologues is proud to be an Evergreen podcast, and was created by Adam Sockel. It was produced by Adam Sockel and Sean Rule-Hoffman. And if you are interested in this podcast and any other Evergreen podcast, you can go to evergreenpodcasts.com to discover all the different stories we have to tell.