Bar crawl with ‘Dirtbag Massachusetts’ author Isaac Fitzgerald

On the shelf

Dirtbag, Massachusetts: A Confessional

By Isaac Fitzgerald
Bloomsbury: 256 pages, $27

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There was a time when you could walk into Zeitgeist, a notorious San Francisco bar, and be sure to see Isaac Fitzgerald happily drinking there — and sometime later working the door. As he writes in his memoir Dirtbag, Massachusetts, he fell in love with the place; it became home. After a rough childhood, he has gone much further (Myanmar), fancier (porn) and fancier (boarding school) and has always started new families.

Today Fitzgerald is best known for appearing on The Today Show and recommending books. Not long ago he co-hosted the Twitter talk show AM2DM with Saeed Jones and was a books editor at Buzzfeed. His substack newsletter, Walk It Off, features lengthy itinerant conversations with writers he’s befriended over the years. Combining those efforts is a sunny public persona, a dramatic contrast to the poverty, neglect, and violence that characterized part of his childhood.

"Dirtbag, Massachusetts: A Confessional" by Isaac Fitzgerald

I spoke to Fitzgerald in New York City about his book. We started with a ride on the Staten Island Ferry – he likes boats as much as he likes bars – on a stunningly perfect day. The ferry passed so close to the Statue of Liberty that I could see its golden flare glowing in the sun: a million dollar view. “It’s free!” exclaimed Fitzgerald, and exclaimed again because it is amazing and true and because his exuberance is genuine.

My plan was to interview him over drinks in Staten Island. The result would be a beer-by-beer diary of our (edited) conversation. Unsurprisingly, as bar tales always do, the plan took some unexpected turns.

beer 1

Location: Steiny’s Pub

Several people sit on bar stools in a dimly lit bar.

Steiny’s Pub on Staten Island, NY, site of several beers with Isaac Fitzgerald.

(Carolyn Kellogg)

Isaac Fitzgerald: Let the record show I had a Johny Bootlegger Fruit Punch on the Staten Island Ferry. I’ll start with a Budweiser, but for the sake of candor and honesty, I also had a beer before arriving at the Staten Island Ferry. So technically that’s drink three, beer two.

Carolyn Kellogg: And I almost had a Miller Light Tallboy. You took some atypical paths before becoming a books missionary at Buzzfeed and now The Today Show. What did you like so much about books that you decided to make them your career?

IF: I came into this life a bit different than average. I had a very interesting, unique childhood, but I would be a liar if I didn’t say that my parents instilled in me a love and respect for books, and therefore education, from an early age. Books were an escape hatch, portals to another universe.

I see it as a calling. Because I still believe! I still don’t believe in Santa Claus, I still don’t believe in a lot of different things that I grew up with, but I really, really, really believe in the power of books.

CK: I’m sorry for what you went through when things were bad. How did you decide what to write about your family experience?

IF: It’s an interesting thing: I kept you in the dark for a long time that I wouldn’t write about my childhood. I came up in the 90’s and 2000’s; There have been many books by often straight white cis men who said, “Woe is me, my childhood was so bad.” And I thought those books were done. Sometimes you are overly critical of the things you might actually want to do. Then as I sat down to try to write this book – and essays that were published before the book even became a thing [“Confessions of a Former Former Fat Kid,” “The True Story of My Teenage Dirtbag Fight Club”] — I haven’t been in therapy yet. I hadn’t figured these things out yet. So I kept coming back to this box. It took many, many years. Many deadlines have been exceeded. I kept trying to write something different instead of writing what the book was supposed to be.

beer 2

Still Steinys

Men sit drinking at a bar with a large television hanging above it.

“For me, bar stories and fables have a lot in common,” says Fitzgerald. He calls a storied dive in San Francisco “my white whale,” a subject he hasn’t yet figured out how to put in writing.

(Carolyn Kellogg)

CK: Sometimes people talk about their achievements in memoirs. And you do not?

IF: [Laughs] Oh, this is the first time someone has asked me this question. On your point, there is no Buzzfeed, there is no McSweeney’s, there is no Rumpus. That was a choice. When I realized that my childhood world will be at the heart of this thing, I realized the story I wanted to tell. And I knew if I had gotten to a lot of these other things, it would get a lot more complicated.

CK: But you wrote about porn, so it’s not just about childhood.

IF: That’s a good point. But to answer your question, essays like “Look at how good I am” are the most boring things on the planet in my opinion.

A few more beers…

This is where my plan began to fail. At one point Fitzgerald was telling an important anecdote about something he had read and moved about when he was younger, and then I discovered my recorder was off. Laps were ordered but not logged. Like a homage to Fitzgerald’s home game, Boston’s ’70s anthem “More Than a Feeling” blared out of the bar’s speakers.

I tried asking him about his sections on going to boarding school, where he makes friends, discovers class differences, and gets in less trouble than at home. He was just as open about beer as he was in his writing about masturbating with his classmates, but steered the conversation away from his days as a porn worker. He was part of the early San Francisco alternative video scene produced by; He said he will leave this issue to the writers and activists who have remained involved in this industry.

At one point I dragged us to another bar so I could get something to eat.

beer 4? 5?

Cargo Cafe that serves nachos

A man seated at a table stretches out his hands to indicate the words "Come back home" tattooed on his knuckles.

Fitzgerald at the Cargo Cafe. Asking him about his “COME HOME” tattoo leads to another long bar story — too long for a profile let alone a caption.

(Carolyn Kellogg)

CK: There is a great love for a certain bar in your book. How did you gather all of your stories into one place – and one narrative?

IF: Just for the record, zeitgeist is my white whale, and this essay is just the tip of the iceberg. The joke I’m saying – this isn’t a joke at all – is that I learned to write so I could figure out how to tell the story of Zeitgeist. The essay in the book is about my love for bars as places of community and places of family.

What makes it such a wonderful story is that, just like a room, it’s cheerful and has gone through all these iterations. It was a gay bar. Then it becomes a really serious motorcycle bar. Then it almost becomes a Joker motorcycle pole. Then it becomes a hipster bar. You can still see that there are these people who find their freedom there, who find things out about what it means to live their lives.

CK: What distinguishes a bar story from other stories?

IF: For me, bar stories and fables have a lot in common. Usually there are lessons, but at some point an animal will speak. [laughs] This is not journalism – but there is a truth behind it. I also think a bar can be a place where people can be their most honest selves. Now, if that’s the alcohol, if that’s like, “Hey, you’re a stranger, I’ll never see you again…” There’s something about the – I won’t get into the word here, kind of like the tide – the people roll, they wander. A bar story can be interpreted a bit and that’s what I love about it.

Kellogg is a former Times book editor. Bar crawl with ‘Dirtbag Massachusetts’ author Isaac Fitzgerald

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