All the Misery of Being in Your 20s, But with Jokes

Erin Somers's "Stay Up with Hugo Best" takes on millennial malaise and predatory men, but without sacrificing humor

A deflated inflatable swan that is 100% just getting through the day however it can
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June Bloom is 29 years old, working as an assistant on the late night show Stay Up with Hugo Best when the show says good night for the last time and Hugo Best retires. Hugo is, on the face of it, the everyman Late Night host. He’s what you might expect of a man who has spent years getting away with whatever the hell he wanted to do in the name of funny business. June has read the unofficial and official biographies of the life of Hugo Best, she’s a zealot for his early comedy. And she also knows he’s had problematic relationships with younger women when she says yes to his invitation to spend a summer holiday weekend at his vacation home in Connecticut. June is everything you might expect of a millennial woman in her late twenties living in Brooklyn and dealing with being laid off before she got where she was supposed to want to go. Don’t we know where this is going? Maybe, maybe not. 

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Sure, this is a #MeToo novel. But of course, it’s more than that. What makes the novel Stay Up with Hugo Best so uniquely smart and entertaining is the way Erin Somers handles the questions no one else has figured out how to confront in the entertainment industry. What do we do with the grey-area relationships between two consenting adults with huge power imbalances? Does it always lead to sex? What does it mean to be in your twenties as a millennial woman? Can people change? And, most importantly, what is funny now? What can funny do? Somers tackles the questions (and summons up new ones) by using the very same comedic muscles that have withered in our current political climate. In Stay Up, Somers employs humor to show us that real comedy creates an opportunity to deal with the truth, rather than obscure it. 

Erin Somers and I talked about what it means to write a “timely” book, the history of late night, and where the funny can fit into the dumpster fire of today’s news cycle. 

Erin Bartnett: This book is extremely “timely” right now. (A phrase I’m sure you’re hearing a lot). But obviously, its life is much longer than the news cycle. Can you talk about the genesis of this book for you?

Erin Somers: I originally wrote this as a short story in 2013, and it had the same basic outline, the same 4-day structure, the same characters. I submitted it to a lot of places and it was pretty widely rejected, so I put it in a drawer, and decided to think about it a little more. I decided the reason it was being rejected was possibly because it was too skeletal. I decided to flesh it out to see if maybe the premise could support a novel. I finished in November of 2017. Harvey Weinstein and the beginning of #MeToo had broken a month earlier in October 2017. So it was in the works for years when all that started, and it’s rare, I think, that a book becomes more timely or relevant rather than less, but that’s the way it worked out. 

EB: What is your hope for the book’s reception or interaction with the #MeToo movement? 

ES: I hope, first of all, that nobody sees it as me exploiting the movement in any way. “I saw what was happening and decided to write a book on it to cash in on it…” kind of thing. It would be a disaster to me if anyone thought that. My hope is that people see this as a nuanced portrayal of these grey area situations that a lot of people encounter with men who they have professional or quasi-professional relationships with, that don’t necessarily fall into the classification of misconduct, but are still kind of nauseating and weird. I hope it’s true to that type of ambiguous experience. 

EB: After writing into this grey-relationship, do you think Hugo (or someone like Hugo) is capable of changing? Of being better? 

We’ve come of age in an era of uncertainty. There’s no clear way forward to be successful as an adult anymore.

ES: I don’t know. I hope so. I want them to be able to. But I don’t really know. I think that’s one thing that interested me and kept me working on the book was whether Hugo could change. Is it possible for him to change? I’m not sure I have the answer. But I do think that we have to find some solution or some way that people are permitted to make amends or some way for people to apologize—depending on how horrific their offense was—because I’m not sure that ostracizing people forever for small errors is the way forward either. Not that Hugo’s mistake is small by any means. 

EB: One of the other grey-area experiences you capture is the grey area of adulthood in your 20s. As you were writing this book, do you think there’s something new about the experience of being in your 20s right now? Or are we living out another iteration of an old, familiar struggle? 

ES: It feels new to me. I can only speak from my experience as a millennial, but it feels like a generational thing. We’ve come of age in an era of uncertainty. There’s no clear way forward, there’s no clear way to be successful as an adult anymore. A lot of the structures have collapsed, a lot of the ways of thinking have collapsed, and I found myself, in my early adulthood, very much just making choices based on nothing. Proceeding almost at random, because I didn’t know exactly what to do. And I think that’s a common experience for people my age, people a little older, and people a little younger. Not knowing how to proceed. 

EB: Not knowing what to do can be terrifying. But what I loved so much about this book is the way you handled that experience with humor. I mean, I too, look into the void of the future and can’t help but laugh to kind of endure it.

What I was so excited to see in your book was that comedy wasn’t a force for flinching away from reality, but actually a way for us to deal with and confront reality. Comedy makes us look at things straight, but also in a way we can…I don’t know…live with? How do you think comedy shapes June’s experiences and why was comedy such an important element in the narrative you were writing? 

ES: It’s an important element firstly because my outlook is fundamentally comic. And it was easy to just make her like me. [Laughs.] As you pointed out, it also makes the book more palatable. This isn’t a #MeToo story in the sense that we encounter a really brutal experience. It manages to be light and satirical despite the subject matter. The comedic elements make it easier to tell the truth and, I hope, make people more willing to read it. 

EB: But I also think there’s an important distinction between the monstrosity of the comedy industry and comedy. Because Hugo’s career as a late night comedian is also buoyed by people who are conditioned to look away. It got me thinking more generally about how comedy is functioning right now. Because while comedy can help us confront a lot of things, we are also reckoning with a lot of problems in the comedy world, itself.  And so where does the funny fit in there? 

Did any of this come up in your research on the late night entertainment industry for the book? 

ES: I’m very interested in that tension, but it didn’t really exist in the same way when I was writing it as it does now. The tension was born of this stuff coming to the surface. When I was working on the book, not much had broken yet in the way of comedy world scandals. The Cosby allegations were happening. That was about it. Louis CK broke in November 2017, when the book was already done. But since all of this has happened, I think about this a lot. None of these disgraced comedians—I’m talking mostly about Louis here—have reckoned with any of it in a way that I find appropriate or funny or especially smart. No one has approached it with an iota of courage. Louis’ strategy is, as far as I can tell, to keep doing the same thing but find a grosser audience.

More generally: the whole world is fucked up! A lot of the comedy that’s trying to take on current events right now is struggling. Particularly in late night. Because how do you write jokes about genuinely terrible things? My whole book is about, somewhat, where the funny fits in and whether the format can continue to evolve to meet the culture.

EB: How does comedy affect your worldview as a writer and also just basically as a human right now? 

ES: In general I think everything could be a lot funnier. Everytime I’m reading a book, the most common thought I have is “This needs more jokes.” I wish someone would buy me a rubber stamp that says “Needs more jokes” and I would be able to stamp whatever I’m reading. Comedy is inseparable from my outlook. I don’t know how else it’s possible to proceed. I don’t see how people without a sense of humor are getting by. 

EB: Are there any contemporary comedians that you follow? 

ES: Off the top of my head: I love Rob Delaney, Chelsea Peretti, John Mulaney and Nick Kroll, Paul Rust, Key & Peele. Everyone in the greater How Did This Get Made? podcast universe—Paul Scheer, June Diane Raphael, Jason Mantzoukas, etc. It’s not so current but I still laugh about certain Tim and Eric sketches every day (“Cinco Phone” and “Cinco Urinal” mostly). Like everyone else, I love the new Tim Robinson show I Think You Should Leave. And of course I love a lot of old stuff referenced in the book: Steve Martin, Richard Pryor, George Carlin, Joan Rivers, Chris Rock, Dave Chapelle. I could go on.

EB: Writing advice. Any adages you stick to or mantras? 

ES: I like the Richard Ford quote, “Don’t take any shit if you can possibly help it.” That’s more career advice than a craft thing. But I can’t say I follow that advice a lot. I take mountains of shit.

EB: Can we talk about The MOVIE? So excited to learn that Stay Up with Hugo Best has been optioned for film, and you’re adapting for the screen. What’s that been like? Anything surprise you about adapting the book for the screen? How does writing lines for the screen differ from writing dialogue in a novel? 

My hope is that people see this as a nuanced portrayal of these grey area encounters with men that isn’t necessarily misconduct, but is still nauseating and weird.

ES: Yeah! I’m writing the movie! I always wanted to be a screenwriter; that was my goal initially. I went to film school as an undergrad. By 25 I’d had some failures and saw how hard it was going to be, and I hatched a crazy plan: “I will simply learn to write literary fiction and become a novelist and then adapt my own work.” Ridiculous. Nine years later, I’m shocked and delighted that it worked. (It shouldn’t have. No one do this. It isn’t a sound plan.) 

But anyway, it’s been fun so far. I love revisiting the characters and writing new conversations for them. The book is dialogue driven, but most of the dialogue doesn’t transfer well because it sounds like dialogue from a novel. Even though I try to write dialogue as naturalistically as possible, it’s still too stilted for film. But I am enjoying that I at least don’t have to describe a freaking plant or any of that stuff. 

EB: Did you have feelings about “the book is always better than the movie?” before this, and have they changed? 

ES: I think the book is mostly better than the movie, yeah. Except for The Godfather. But not to worry, I’ll just make it as good as The Godfather.

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