A Book You Will Definitely Return To: A Q&A with Sean Bair-Flannery

Sean Bair-Flannery’s new book Places I Can’t Return To: An Accidental Memoir is unlike any other book I’ve ever read. How funny is it? As a gauge, think about your favorite humor writers. Add up all the laughs they’ve given you. Multiply that number by infinity. Sean’s book has more laughs, more delicious moments, more delightful turns of phrase, more joy than whatever number you just calculated.

When the Chicago Reader named Sean the best comedian in the city, it made obvious sense. I’ve seen Sean’s standup and one-man show Never Been To Paris many times. Every show I attended was sold out. One time, my husband and I unwisely showed up to NBTP at the old Lincoln Lodge without advance reservations. There wasn’t an empty seat in the house. Sean himself took time out –  within moments of going on stage – to personally find us a space.

That’s the kind of person and comedian that he is. Wherever he’s performing, whether it’s on Comedy Central’s This Is Not Happening, at his critically acclaimed Blackout Diaries, or at a bar in Chicago, the audience rocks with laughter as he recounts all the times he nearly accidentally offed himself along with other true tales of well-intentioned mayhem.  

So when the Chicago Reader subsequently named Sean “the best drunk in the city,” I had questions. True, many of Sean’s stories (but not all!) take place under the influence. And from those stories, it’s clear he is a hilarious, adventurous, fearless, heedless of consequences, completely original drunk.

But he is so much more. The backdrop to all these shenanigans is Sean’s philosophy of life and it’s actually quite sober. A long time ago, Sean committed to living each day like it’s his last. He resolved that life is short, so he would have a good time pursuing only the things he finds most interesting and fun without caring about money or how he’s perceived. What happens when you live life so fiercely? For one, there will be places you can’t return to. Apparently, it’s worth it.

The book is not a retelling of Sean’s standup. If you’ve been to his shows, you’ll recognize some tales, but these pages contain juicy hilarious details, behind-the-scenes dialogue and epic stories that he has never before revealed in public. It is not overstating to say each chapter is legendary. It’s testament to Sean’s economical storytelling that chapters are short and you can read them in any order. The amount of comedy packed into each page is a miraculous gift to readers. I found I could not read the book at night because I was laughing so loudly that I kept waking my husband.

By way of just a few examples, if you’ve heard Sean’s trademark story of flying off a multi-lane highway bridge in Cleveland in a blizzard, you’ll now learn even more about what went on inside the car during that “flight”, where Sean and his passengers were headed and whether they ever arrived. Remember when Sean electrocuted himself during a job interview? There’s more to that story than we knew. Or you think you know the one about the Huey Lewis concert, impersonating “Bob Doppell” and walking off the roof? Well, wait until you read the book.

And did you know that Sean once allowed the state of Illinois to turn him into a woman? Or that he’s attended the wrong wedding – twice? Or that his children and nephews inherited the comic genes? I’ll say only that a situation unfolds atop a McDonald’s jungle gym. It was one of the places where I accidentally woke up my husband. Speaking of family, how did his wife Jessica react when he was named “Best Drunk”? And has his perspective changed now that he’s a father in his forties? Read this book for these answers and so much more. Sean kindly emailed with me about his authoring process and gave me intel on where you can see him next and even score a signed copy of Places I Can’t Return To. Please help make this book the bestseller it deserves to be. You’ll be so happy you did.   



Teme: When did you decide to write Places I Can’t Return To?

Sean: Many years ago I did a one person comedy show called Never Been To Paris about the last ten times I nearly killed myself by accident. Honestly, I wanted to write about a book version of those stories ever since, but I never found the time to make a lot of progress. I had the structure of the book in my head and I wrote out a few of the stories and posted them online, but the book never came together as a cohesive project.

Then, lockdown hit and all my shows were canceled. All the time and energy I was previously devoting to live shows – writing, performing, marketing—was now free and I allotted all that time to writing Places I Can’t Return To.

So, to answer the question, I wrote it last year, over a decade after I had the idea for it, because that was the first opportunity I had to spend the needed time on it. But, in a way, I’m glad I had to wait so long. I think this book – it has a lot of drinking stories in it—reads better when told in my forties with three kids, versus if I had written it back when I was still partying each night.

Young men have too much pride when telling drinking stories, which often ruins the humor of the stories. By writing it later in life, I think I tell the stories more matter-of-factly, with neither shame nor glory, and I think that reads funnier than a guy wanting to prove he’s a good time.

Teme: When did the stories in the book take place?

Sean: The stories about getting fired from jobs all took place from about 1992-2002 and the drinking stories took place from about 1996-2006, so, yeah, the ‘jack ass’ stories all happened in about a 15 year stretch. The family stories obviously took place before then, mostly in the 1980s.

Teme: What is the secret to being as hilarious on the page as on stage? What is the secret to writing the funniest details, descriptions and dialogue?

Sean: This is a balance that was always in my mind while working on the book so I will confess it did not necessarily come around naturally. Most the books I’ve read by standup comics read like a transcription of their live act and that was something I consciously tried to avoid. If you are converting spoken stories to prose (if I can use a word as scholastic as “prose” when talking about getting drunk and walking off roofs), I believe the entire structure of your story should be re-evaluated for the written page as everything from word choice to transitions and character roles is affected by the change in medium. So I was always pushing myself to reexamine if I was writing this story in a certain way only because that’s how I tell it to people on stage and, if so, should I consider changes.

But, and this is why it was a balance, I also wanted the book to read like you knew me, where I was accentuating the same things in the book that I do on stage or in person when telling a story.

To achieve that balance (in so far as I did), I used a few strategies:

1. I posted a lot of preliminary chapters to Facebook which helped to keep the stories simple and brisk. People won’t read boring or rambling things online so its good training for writing straightforward content. Probably the biggest lesson I took from standup and applied to this book was concision of details. In standup, crowds find it easier to follow, and in turn they laugh hardest, at stories where they are not balancing a lot of details. So I tried to never introduce a character’s name or sex unless it was absolutely necessary for understanding the story. I feel that every detail an author (or storyteller) introduces is one more ball the audience (or reader) is contemplating. People have a natural wish to “get” art or stories, and they try very earnestly to follow along, which I think can work against you if you are throwing too many details at them (at least in humor). I wanted the reader to only focus on the most important parts of a story, so I was always focused on eliminating superfluous detail.

Posting rough drafts online really assisted with that.

2.  When writing dialogue, I say the exchange out loud, with the voices I picture (or remember) for the characters, to see what sounds best, then I write that to the page and read it. If the reading of that captures the same energy of saying it out loud, I don’t touch it. Sometimes I need to adjust for the written page – change a word or a concluding though here or there — but the key, for me at least, is to say dialogue out loud before writing it down.

Teme: What was your writing process like?  Did you keep notes or just have a great memory? How did you prepare to write -what snacks, activities, motivation fueled your process?

Sean: I wrote exclusively at night. For the first third of the book, I drank Manhattans while writing. The second third was martinis and the final third was negronis. But, the order I wrote the book in, is not the order of the chapters, so there’s no easy way for the reader to figure out which cocktail generated which chapter.

I always wrote at night, after the kids were in bed. Adam (“The Cane”) Burke, my editor, said on some nights he could read me getting drunk – he could almost see it like bar camera security footage– because the first page would have my normal level of mistakes but, by the fifth cocktail, the pages looked the manifesto of a crazy person, written in their second language.

On remembering the details of the stories: I keep notes, yes. My whole life, even before I started standup, I wrote letters and emails to friends nightly on what happened that day, so I have these semi public diaries to return to and find details. And I additionally contacted all the people in the stories (that I still know or could find contact info on), to see how my diaries and memories compared to theirs and that was really interesting.

There is a kind of hilarious, Rashomon effect to whiskey because every person I contacted remembered the story slightly differently but had this funny consistency where each person fashioned themselves the one sober participant in the story. This is how every exchange went:

TED: “Yes, Sean, I remember that night, because I was sober, but you and Willy were A MESS!”

— then you call, Willy —

WILLY: “Oh yeah, I remember that night. I remember it because I barely drank but you and Ted were drunk and OUT OF CONTROL!!”

To answer the final part, ha, no snack but I probably drank about 1,000 calories worth of whiskey or gin each night so I never wanted for energy.

On Re-Writing (and the process): Another ‘benefit’ of COVID, in terms of how it made the book possible, was that my buddy Adam Burke’s shows were canceled. Adam is an amazing comic, great friend of mine, and a trained editor so, because he had no shows, he was looking for both money and a project and was able to edit my book.

Prior to working with Adam, I had, over the course of five or six years, accumulated about 80 pages of the book. I began working with him and, in less than a year, we completed 600 pages. After reading the 80 pages I had, Adam gave me great writing advice:

“The reason you’re not making as much progress as you want is because you are trying to edit while writing. Editing is now my job. Don’t do any edits. Think of it almost like a brain dump, and we edit later.

No one can do two really hard jobs at the same time and you should not either.”

So I started writing with almost no changes or second-guessing, knowing we would do that part of the process later. It was a huge productivity boost. Which means, yes, I did a TON of re-writing but re-writing is less tedious if you don’t think you’re reaching for the stars on the first draft and, instead, are just getting your best ideas on paper, to be fleshed out later.

Teme: What is your favorite story about writing the book?

Sean: Well, as I said, Adam often said he noticed how I was drinking throughout the night, and I do think he had the patience of Job to edit the book. He had me use Microsoft Word and it has this feature where each correction has an explanation on the right side gutter of the document, but – if you write as imprecisely as me—the volume of explanations can’t fit on the same page as your content, so Word creates all these rays that point to them off screen and I always said, the image of all those lines exploding off the page looked like the diagrams that scientist release after they collide atoms, where an infinite amount of particles expand from a single point.

Additionally, Adam, God love him, would always have more faith in my mistakes than I deserved. I can’t remember the exact situation, but on one page, I misspelled a word so greatly it wasn’t obvious what I was trying to say and Adam, attempting to take it seriously, replies, “the word you have here is technically a word; it’s an Iranian flute that can sometimes be used as a weapon. Is that what you meant?”

I remember laughing for ten solid minutes that “The Cane” thought I knew about archaic Persian weapons and purposefully brought them into a story about drunk swimming in Cleveland.

Teme: What are your favorite stories in the book?

Sean: My favorite chapter is “Cleveland Municipal Stadium.” My favorite story is probably from Ripley’s Believe It Or Not, on how we tried to get fake IDs. My book also has a lot of asides, where I talk about science or history or local celebrities and my favorite news story or aside was the guy who locked himself in a cooler of beer in Wisconsin on purpose.  


Teme: You write, “The entire point of drinking is to forget reality – to mute the forever background panic of your mind- which … not only helps us survive bad injuries, but, I would also argue, life. Life is a harpoon to the chest that just bleeds slower…” (page 197). Does comedy also help people with that constant background panic and life’s slow bleed?

Sean: Yeah, I think comedy is definitely a good and healthy coping mechanism. I’ve always felt that comedy and booze are the best anti-anxiety platforms on Earth and to argue differently is class warfare (have you ever noticed that all the people who knock alcohol as a coping mechanism live in a mansion overlooking a beach and have wrecked 7 corvettes?).

Comedy and laughing is great to get past panic and anxiety because, not only does laughing feel good (many studies have shown the physical health benefits to laughing a lot), but it’s also has a great interlocutor effect where, when you make a joke about a sad situation, the person you are talking to starts laughing and maybe sharing their own experiences, versus just saying “well God has a plan” or some dumb, meaningless platitude.

I’m not proposing that, when you go through trauma, it’s your responsibility to not make people feel awkward, rather, you can use humor to control the dialogue and push people towards discussing the topics you wish to discuss.

Teme: You write, “It’s more important to accumulate good stories than good decisions.” I love that. Do you still feel that way?

Sean: 100%. Some people say, “you can’t take it with you”, when talking about money and the afterlife and how you should spend it now, but I’m more provisional- I don’t think you should even “make it”, if it’s not leading to fun memories. The ‘it’ for me is just memories. I don’t think anything else matters.

I grew up in an enormous Irish Catholic family. I’m the oldest of six. My folks were both one of eight and all their brothers and sisters had a ton of kids. On top of that, my dad worked for The Catholic Diocese, which meant I was attending funerals and wakes all the time. It made a huge impression on me.

At these events, I would talk to old people that knew the deceased and, after the small chat, they would always say the same thing- “well, Sean, have fun while you are young because, believe me, IT GOES BY FAST!”. And I thought about how fast grade school went by for me, then high school went by even faster, and college was a blink, yet these old people are saying the second and third act goes by faster yet even though it all keeps accelerating. And it made an impression on me that, even if I have a lot of time on earth, it ain’t a lot of time.

So I always wanted to build memories more than anything else. And I think you often build the best memories when you say ‘yes’ to everything around you, even if there’s no plan and that ‘yes’ was built on nothing but miscalculations.

Teme: What part of your life philosophy from those early years have you brought to your life now and what has changed?

Sean: It’s weird because on one hand, everything is the same and on the other, it’s all different. I still am mostly focused on trying to have a good time. I still pursue the things that I find most interesting and fun- I don’t worry about money or how I’m perceived. But, when you have three kids, you’re also thinking about if you are providing enough so, in that sense, everything is changed. I don’t do reckless things anymore. I have predictable, safe nights. I don’t get fired from jobs anymore- I’ve been at the same place for almost 20 years now!


Teme: How would you describe yourself as a parent and how do you inspire your kids to have the same kind of resiliency, creativity and independence of thought that you have?

Sean: I try to be a good parent but my approach to parenting has almost nothing to do with my comedic act  or the book. In fact, my kids often joke about how they hear from neighbors or party guests that I’m a comedian or I wrote a funny book, but they don’t see it in me because I’m a mostly strait-laced parent.

I’m very different as a parent than I am as a performer or author, but I love doing art projects with them and encouraging creativity. I also encourage them to be independent thinkers, where they should think about a question before googling the answer and try to work it out themselves.

The only part of my parenting that probably relates directly to my creative career is, I always tell them that they should pursue the careers they are most passionate about and not worry too much about money.

Teme: What will you tell them about the stories in the book?

Sean: Because my parenting is so divorced from my standup and the book, and because they don’t care that much about that aspect of my life, it’s not an issue.

A funny thing about my kids: I’m very good at drawing. When I was a kid I wanted to draw comic books as a career. I quit drawing, probably in high school and got more into writing, but when I had kids we started doing art projects together. The kids will show me something they want a drawing of on the computer and I’m very good at duplication, so I can pretty much draw that exact thing for them to color in.

Every time they hear an adult compliment my comedy, they say, “I don’t know why he tells these jokes for strangers. Were the jokes even funny? Have you seen him draw? He has real talent at drawing. He’s good. The joke stuff?? We don’t know about that. ”


Teme: How did your sense of humor and outlook help you and your family through our recent crazy times?

Sean: We kept our sense of humor no matter how crazy or dark things got. One story that sticks out just because it’s both funny and kind of serendipitous:

In early 2019, my wife signed us up for WHO GIVES A CRAP, which is a service that mails you eco-friendly bamboo toilet paper. Bamboo toilet paper has a smaller carbon footprint and they donate a percentage of their profits to create modern toilets and plumbing in needful countries.

We got the first enormous box from them in February and my wife explained what it is and what they stand for.

“What do you think?”, she asks.

“I think the human body does three or four acts a day that have nothing do with the death of this planet and this is one of them”, I answered, considering it a grift.

But a month after that first box was received, toilet paper sells for more than cocaine online and half the city is waiting overnight at the grocery story, like it’s Black Friday, for the right to buy one roll on shipment day and we get a letter from WHO GIVES A CRAP a week later that essentially says,

“So, as you have prob noticed: things are crazy in the toilet paper world right now. But, no worries! We made a boat load of bamboo toilet paper and we are going to keep shipping all your toilet paper each month, on time and no price changes. After all, we are, WHO GIVES A CRAP!”

Without me realizing it, my wife essentially bought toilet paper futures and we were set for the pandemic. This is a common, funny theme in our relationship where, whenever my wife and I have a financial disagreement, the day after our conversation some event happens that makes national or even world news and it completely proves her side.

Teme: What are you thinking when you get up in the morning and what makes a day worthwhile and well-lived?

Sean: When I wake up, there is one question: “Jessica, do you need to work this morning or not”. She co-owns a daycare so if she says “yes”, that’s terrible for me because it means I have to get the kids ready for school. If she says “no”, I go back to bed and it’s the best day of the week.

To me, it’s a good day if I didn’t get fired from my job and everyone is healthy, which is an upgrade over my father. He used to say it’s a good day because “I didn’t lose the house and no one is dead”. This is second generation, Irish joy-inflation. His bare minimum was being alive and not homeless, but I have graduated – or perhaps some would say softened– to expecting employment and not being sick as a good day.


Teme: You’ve mentioned that your stories often inspire others to tell their stories – what are some of the most surprising or greatest stories that you’ve heard?

Sean: Yes, in fact, Blackout Diaries, came from me performing Never Been To Paris. I did a 2-year run of NBTP at The Comedy Bar (the show was mostly about drinking stories) and, after each show, crowd members would approach me afterwards and tell me their own drinking stories where they nearly died and many of them were funnier than mine.

I created The Blackout Diaries to put people like that – everyday Chicagoans with hilarious drinking stories – on stage. And I’ve heard so many hilarious, crazy, unexpected stories since then.  These are the ones that stick out right now:

* one guy, which I think is the best advice I ever heard at the show, talked about how he keeps a handcuff key on him. It turns out all police forces and security guards order the same handcuffs and this guy and has basically escaped four arrest attempts by keeping a key in his pocket.

* another guy told a story that I think is so Blackout Diaries where it’s equally hilarious, scary, shameful and privy. He approached me, said it was the greatest drinking story he heard, but he was not allowed to tell the story until the person died and they had passed-away recently. His friend was driving drunk in the 1980s and reached a DUI checkout point in Illinois. He was driving a huge black Cadillac and knew he wouldn’t pass the test, so he jumped in the backseat and pretended to fall asleep.

A line of honking cars built up behind him. The officers walked up to his car and banged on the glass, waking him up:

“Where’s Juan??”, he enacted, quizzically.

“WHAT?”, yelled the cops.

“My driver. Juan. Where is he?”

He then explained he had a driver who might have run into the nearby forest, confusing this for an immigration check.

The police officers shutdown the checkpoint and all ran into the forest to tell Juan this was not an immigration sting.

They told the man to just drive home.

“I can’t! I’m drunk God damnit. Juan was my driver!”

Their lieutenant drove him.

“Actually, I’m not going home”, he corrected, “I’m going to the Green Mill”.

He was driven to the next bar by their leader, while they looked for his imaginary driver in the forest.

Sean Flannery Book Photos – 8/12/21 Photo by Chris Ocken Copyright 2021 – https://www.ockenphotography.com/


Teme: Your appearances on Comedy Central’s This Is Not Happening were so excellent! What was the process of getting on the show?

Sean: Thank you! The co-creator and producer of TINH, Eric Abrams, had seen me before at Blackout Diaries and Never Been To Paris (I’d like to think BOD inspired TINH, but that’s prob not true). Eric has always been a big fan and supporter of mine and he sort of fought for me to have an audition, so it was a big honor to audition and then do the show.


Teme: What do you hope people will take away from the book and from your shows?

Sean: I honestly hope that what they take away, from both the books and the shows, is that cars are evil and that you will be most happy in a city that doesn’t require cars, as you can live and drink and smoke however much you want, not having to worry about merging onto a 4-lane highway ten minutes later.

I really believe that’s the point. Burke says, “No, you barely touch on that” and he thinks the point is to trust your instincts about having a good time, knowing it could all end tomorrow, and never look back.

But I say that’s only possible without cars. 

Teme: What question(s) would you like someone to ask you – about the book, comedy or life – and how would you answer?

Sean: I think an ongoing theme in my book is job interviews and the power dynamics of employers insisting on obsequiousness from you, while providing nothing like that on their end. I was borderline reckless with my job interviews. Certainly, fearless and interviewed for jobs I didn’t deserve (why not- employers interview people that are overqualified and then undervalue them all the time, so why shouldn’t I do the reverse and promise to work the job without knowing it?). I lied and conned my way through interviews and, overall, I think it built a skillset where I learned to interview really well at jobs.

I’m sort of surprised no one coaches this- I think people should be fearless, kind of indomitable with job interviews. If you think you are remotely qualified- try it. Every job interview is a skill learned and you help equalize the power dynamic , where you are becoming as comfortable in this situation as them.

A lot of their power comes from the asynchronicity. They have conducted hundreds — maybe thousands of interviews — and you have only done a handful.

But if you are some jackass, lying your way through this semi functional dystopia we call “the service economy”, perhaps you have been on more interviews than they have conducted. Now you have the power!  I routinely answer interview questions like a Supreme Court nominee- “You have to hire me to discover that”. I say, “I won’t answer that until you answer these four questions”, and they never come back.

Take their power away. Come in more confident than them, like you are interviewing them, to see if they know how to interview.


Teme: How has Chicago influenced you as a person, comedian and writer?

Sean: Deeply, at all levels. As a person, I’ve made friends here from wildly different backgrounds and learned from perspectives I would have never encountered if I had not moved here. This has opened up a lot of narratives and experiences that were invisible to me before moving to Chicago.

As a comedian, it’s helped me because the comedy scene here is so vibrant and creative that it pushes you to be funny in original ways. As a writer, I’m not sure it had a direct impact, other than the Chicago comedy scene influencing my sense of humor, but it probably, in some ways, de-mystified writing a book.

I think one of the barriers a lot of people have to being creative – or at least this was true for me when younger—is that you think a project like writing a book, or an occupation like standup comedy is for “other people”- people who grew up in environments that were different than yours or had training different than yours. People that were more “meant” for it. But, living in Chicago and meeting more and more artists, I came to realize- the only thing these people have in common is they just tried it and stuck with it. Their backgrounds are from all over the place.

Since the book came out, a lot of people have told me they always wanted to write a book and I always respond, “do it” and they usually decline with something like, “oh no, it’s just an idea I have in my head, I could never do it”.

I think moving to Chicago and consistently meeting people who tried weird plans- I think that indirectly helped me believe that I could do things I would have not otherwise attempted.

Teme: Will you be writing another book? (Hoping yes.)

Sean: Yes, I have not started it yet because there’s still a lot of work to do on Places I Can’t Return To. I’m still converting some of the files to different formats for sale on different distribution channels, and there’s a lot of marketing work I need to do on this book before I consider the project done, but I’m hoping to start the next book soon. I have the title and general structure in my head and I’m hoping that I enjoy writing it as much as I enjoyed Places I Can’t Return To. I think people will find the next book interesting and I think it will have a much wider appeal than Places I Can’t Return To.


Teme: Please let people know where they can see and hear you! (And can people get signed copies of your book?)

Sean: I’m doing an interactive ‘reading’ of my book at Mrs. Murphy’s And Sons Irish Bistro on Sunday Feb 26th at 7 PM. It’s going to be a fun way to bring the book to the stage, where the audience will pick which chapters I’m going to tell the stories from and, while telling it, I will have photos from the events and we might even get a few other people who were at some of these events to join me and offer their perspectives (or corrections!) to the stories. I will be selling autographed copies of the book at this show and its hosted by my editor Adam Burke. It’s going to be a really interesting experience, I think-

TICKETS: https://www.eventcombo.com/e/Solo-Sunday-Presents-Places-I-Cant-Return-To-by-Sean-Flannery–67410

And, online, I’ve been releasing the audio book as a podcast, also called Places I Can’t Return To, so you can listen to the chapters as they are released wherever you find your podcasts. Additionally, I host a podcast with my buddy CJ Sullivan called The Blackout Diaries where standup comics plus everyday people tell true drinking stories. We release a new episode every Tuesday.


More about Sean and Places I Can’t Return To: An Accidental Memoir at seanbairflannery.com.

Tickets to Sean’s interactive reading at Mrs. Murphy’s and Sons Irish Bistro on Sunday, February 26 at 7 p.m. can be purchased here.

Tickets for The Blackout Diaries at theblackoutdiaries.com.

Follow Sean:

website: seanbairflannery.com

Twitter: twitter.com/sean_m_flannery
Instagram: instagram.com/seanbairflannery
Facebook: facebook.com/seanbairflannery

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