Bob Eckstein is an award-winning writer, New Yorker cartoonist, and author/illustrator of The New York Times best-selling book (and postcard box set!), Footnotes from the World’s Greatest Bookstores.
Last summer, in a webcast interview from his New York-based studio, Bob shared with Clarisse (aka CStar9) his love for endangered bookstores, admitted he used to send toast through the mail, and urged creative people not to work alone.
- For your World’s Greatest Bokstores project, why bookstores? And how did you narrow down your bookstore choices?
There were many different reasons why a store would be chosen: its historical significance, its importance to the community, maybe its beauty. Main-Street bookstores play so many important roles in a community, and I wanted to capture these in the book.
I have a great interest in story: people want to read something with meat on the bone. Luckily, bookstores are magical places. I profiled about 150 to 200 bookstores, and then had to choose half. I was hoping there would be a sequel!
- You’ve written books about the bookstores of the world, but you’ve also written about snowmen, cats, Arctic explorers, and more. What does research look like for you?
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Each of these books would have taken much longer without the internet. I make every attempt to visit and learn from a subject in person, but that is not logistically realistic, so sometimes research comes from surfing the web.
Once I find out everything I can, I try to simplify and curate the interesting stuff. That’s the glamorous part of writing a book. But eventually there comes a point where you have to stop doing that and just start writing.
- You write for TV, you write prose, you paint, you are a cartoonist… Is there a medium that feels most like home for you?
It’s so much fun to create a cartoon that makes people laugh. And writing is something that I am certainly at home with.
I juggle many different things in my career. I’m a public speaker, I teach, I do cartoons for different magazines, I do illustration. It’s hard to make a living from this stuff. You have to produce a tremendous amount of work. At the moment, I’m working on four different books.
I write almost every single day. For the last few years, I’ve been waking up by 5:30 a.m. to start writing. By 9:00 a.m., I usually finish a piece. Then I can get started with the rest of my workday. That discipline is how I get so much done. I also don’t watch much TV!
- You’ve said in an interview, “My deadlines are relentless [and I don’t doodle for fun]. If I’m drawing, it’s with a purpose.” Do you ever get creator’s block and if so, what do you do about it?
I have lists of ideas I don’t have time to get through.
I don’t get writer’s block, where I’m just sitting around for an idea or joke to fall into my lap. The way I teach others how to get out of ruts is this: usually it’s a matter of tuning in to the voices and ideas in your head. These days the world is a very loud place. We are all inundated with distractions and sensory overload. Taking a walk or just even taking a bath to be alone with your thoughts…it’s surprising how easy it can be to come up with ideas during those times.
You also can’t work alone. I believe the best gift a creative person can have is the ability to surround themselves with talented people.
Anything I’ve had success with can be traced back to someone who helped me: someone who gave me encouragement, who inspired me to explore something new, or who gave me a professional opportunity.
- How do you narrow down your ideas?
There is so much rejection in this field. So, basically, I fold up as many paper airplanes as possible, and then I chuck them out of the window and see which ones stick.
I never actually intended to do postcards. But the opportunity came, and I went with it. I didn’t appreciate initially that the Bookstore postcards would go over so well. I always just cross my fingers that people will have a chance to see the things I work on. I know I usually sound like a have an ego the size of God’s cigar, but I was genuinely surprised to hear that for example, students were wallpapering their dorm rooms with the Bookstore postcards.
- What’s your relationship to postal mail?
I love postcards. I have sent thousands of them – really! I used to send out mailings in groups of a thousand to potential art clients. I also sent jokes like poly-ethylening slices of toast and writing “Keep in toast” in yellow plastic that looked like squeeze-on butter. I eventually mailed them in plastic bags after sending hundreds with just putting a stamp on the piece of toast. Today I probably would be arrested.
I dearly miss the age of regularly corresponding with hand-written postcards. This year I sent maybe only a hundred. Email has ruined it, postage increases has ruined it, younger generations who don’t even write in script anymore has ruined it. I know I sound like an old man yelling from his porch, but it seems everything I love is going extinct -—from old-fashioned postcard correspondence to vinyl LPs, MAD magazine, and gag cartoons. I try to be a help. I raise awareness about the plight of disappearing bookstores. I’m writing a book now on our most important museums, and I’m working with a friend on a film that’s partly about climate change.
- You do live drawing for events. How did that come about?
When I was a kid, I loved Sports Illustrated, and they would do drawings of sporting events. I eventually worked for them and was also a sports reporter of sorts for The Village Voice and The New York Times. So, it was natural for me to incorporate my humor and artwork to coverage.
I used to take-over the Times website front page for the Super Bowl, Olympics, or World Series. Then I did it for The New Yorker: the Oscars, Golden Globes, etc. I still live-draw occasionally to promote cultural events. It’s perfect for today when people want to see stuff as much as they want to read about it.
It’s also an example of how I like to always push the envelope, which artists and writers should always do. I’m always asking “what if?”.
It’s like the squirrel operetta I tried to make. What if?
- What are you most proud of, outside of your writing and art?
It used to be my hair.
I’m very proud of my wife. She is a well-known book artist and a total bad-ass—she will hate this answer and I will pay for it later. But that’s what being a bad-ass is all about.
- What advice would you give your 10-year-old self?
Growing up, there was no one who said, you’re funny, or, you should be a cartoonist. That didn’t happen until I was surrounded by friends very late in life.
My friend and mentor Sam Gross – who happened to be a cartoonist for the New Yorker – organized my birthday party one year. That party also happened to be the regular New Yorker staff lunch. The food was very good. I asked if I could come the following week and he said sure, but you also should make a cartoon and submit it to the magazine.
So I took up his dare, and the New Yorker ended up buying and publishing the first cartoon I drew. I realized later it wasn’t as easy as that. But it opened the door.
I always say to my students, you’re never going to have these things happen if you don’t show up. 80% of success is just showing up – being willing to listen to and learn from people. You never know when something life-changing is right there in front of you.
- What’s next for you? And importantly: what postcards can we expect next?
This summer, I spoke at the Humor Writing Conference. A few times a month, I produce my Substack newsletter, The Bob, which has turned into a huge, pleasant surprise. I have a handful of magazine assignments to complete. As I said, I’m working on four books.
And I am looking to make a box set of postcards in 2025, of museums in the U.S.
- We can’t just leave on that cliff-hanger! Tell us about the museums postcard project!
I covered 155 museums for this project. Like with the bookstores project, I visited as many of the museums as I could in person. But for those I couldn’t visit, I sent friends and other ambassadors to report back to me with their impressions and photographs.
When I went to a museum myself, first I would just go and experience the place holistically. But in the back of my mind, I was always thinking, what’s the best angle or the most unique view of this place that would create an incentive to people, to say, Oh, I’ve gotta add this place to my bucket list.
An example is the American Museum of Natural History, which has an iconic blue whale that hangs in the main room of the oceanic division. I felt like it would be delinquent on my part not to give people what they expect and want to see in a view of that place. And then I would make supplemental illustrations to pique additional interest. I hope people will feel a real sense of wonder when they’re exploring this project, whether they’re looking at the Museum of Fine Arts in Boston or the SPAM Museum in Minnesota. It’s just mind-blowing that all these places exist.
I want to add that I’m still sad that the bookstore book ended. It was the same with the museums project. I did three illustrations a day. I put my heart and soul into this project and slept very little. But I didn’t mind the long hours because it was such a fun thing to do.
Editor’s note: Footnotes from the Most Fascinating Museums is about to be published — it’ll be out on May 14. Hopefully the corresponding set of postcards will soon follow! 😊
To learn more about Bob, check out his website and newsletter! Bob has given interviews about the long and winding road to becoming an author and cartoonist, about humor, about his book The Complete Book of Cat Names and also been interviewed for the New Yorker Cartoon Caption Contest podcast. For the aspiring writers out there, he has some tips on publishing and writing on Writer’s Digest.
And now, for the sneaky giveaway: Clarisse is going to send 4 postcards from Bob’s World’s Greatest Bookstores set to 4 randomly picked postcrossers! 🎉 To participate, leave a comment below to share your favorite bookshop. Come back this time next week to check out the winners!
And the winners of this giveaway, as chosen by Paulo’s random number generator are… weesnet, traceyinwd, JillRock and MZLA! Congratulations, and thank you all for participating!