5 Questions For A Comedian: Bob Eckstein

OK, so he's not a comedian, but he's still pretty damn funny

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Bob Eckstein holds the honor of being one of the most interesting people I know. I met Bob virtually during the pandemic. We connected over Zoom, and chitted and chatted about ways our comedic worlds collide.

Bob is an award-winning illustrator, New York Times bestseller of his book, Footnotes from the World’s Greatest Bookstores, New Yorker cartoonist and world’s leading snowman expert. He has been drawing for countless publications for decades. He is extremely knowledgable of cartoons and cartooning (and very funny), and in addition to selling countless comics in all variety of print and digital outlets (seriously, it seems like he has something running somewhere daily), he also teaches, consults and works in many aspects of the illustrative arts.

And he writes fantastical books, such as his latest:  Footnotes from the Most Fascinating Museums: Stories and Memorable Moments from People Who Love Museums.

The book is beautiful, as all of Bob’s books are, and features his fantastic, dreamy illustrations and stories about over 75 of the coolest museums in existence.

I’m honored to have a little blurb featured in it about an early date I went on with my husband to Philadelphia’s Mutter Museum:

1. What would you say to someone who told you they were about to start a career in gag cartooning today? 

Unfortunately, seldom does anyone nowadays think of cartooning as a livelihood. It’s pretty much just recreational. I was forced to stop and take a job as an Art Director, went into teaching and speaking and focus on writing books. MAD, Barron’s, Harvard Business Review, Playboy and a handful of others all stopped, at about the same time, no less. The big money promised for online cartooning hasn’t materialized. So if someone told me they were about to start a career in gag cartooning, I would encourage them to continue cartooning for pleasure and fun, great reasons in themselves, but to have realistic expectations. (This doesn’t apply to animation, and other forms of cartooning which I never was involved in.) 

Everyone can play tennis. You don’t have to be on tour. 

Pretty upbeat way to start the interview, eh?

2. Is your spouse supportive of your work? Give an example.

My wife has been tremendously supportive to me as a person and as an author. She is always concerned that I am overworked and tries to convince me to say “No” to jobs that don’t advance my career (I don’t listen). She even proofreads my writing and critiques my art. My work would not be at the high level it is without her involvement. 

As for cartooning, she is not supportive, at all. She knows all too well the anguish and disappointment the field brings me, personally and as a whole. I should clarify, my time as a cartoonist is just a few years. I sold my first gag cartoon to The New Yorker in 2007. But I have been writing humor for forty years and was a columnist since I was a teenager for New York Newsday, The Village Voice and then dozens of publications since, like SPY magazine. At the moment I do a column for Writer’s Digest, Funny Times and appear in American Bystander, LitHub, Atlas Obscura and others. I’m also finishing my eleventh book and first script. Ideally, I WOULD trade that all in and do cartoons full-time, but it’s just not possible right now, not for me, at least.

(I tried to rejuvenate the cartoon field by producing a series of “Best Of” cartoon collections through Princeton Architectural Press, but the appetite for classic New Yorker cartoons has, sadly, waned and the timing of their release during COVID was unlucky.)

3. Did you see the aurora borealis last weekend? Ever?

No. I drove to the parking lot of the church on the hill where, on Facebook, locals claimed everyone was meeting for the best viewing. I sat there in the parking lot for hours, alone. No one showed up and there was no light show, to speak of.  

While doing nothing, I remembered a list I did sometime back in the 2000s, my Dream Dinner Party. To the best of my memory it included;

Benjamin Franklin

E.L. Doctorow

P.G. Wodehouse

Dorothy Parker

James Bond

Neil Armstrong

John F. Kennedy

Sylvia Plath

Caravaggio

and Martin Luther King

While listening to a man screaming obscenities into his phone from a nearby house, I had a revelation and decided it was time to be honest with myself and amend that list without being pretentious. 

My Revised Dream Dinner Party

Bill Murray

Jennifer Coolidge

Scarlett Johansson

David Spade

Stormy Daniels

Jon Bon Jovi

Richard Kind

George Santos

4. Is it better to be a cartoonist in Pennsylvania or in New York City? Why did you choose the place you chose?

Neither. Try Oregon. I moved to Pennsylvania for its beauty. I may move away for its politics.

I set up a dream office creating a replica of a ship’s Captain’s quarters in my attic to write my next novel, The Sea Below Us, an 1850 diary written by a stowaway in search of the missing Sir John Franklin in the North Pole. How’s that for an elevator pitch?

5. What is your favorite cartoon you ever drew? 

I’m saying the guru one—it went viral and its what I am most known for.

But I really like this one because it includes two of the three men who meant most to me growing up (I couldn’t fit my dad in the row boat).

What is a favorite someone else drew?

This one, by the late, great Jack Ziegler, who single-handedly changed single-panel gag cartooning. This clever example smashes our notions of what a cartoon can be when it first appeared in 1987.

Ed. note: Here is one of my favorite Bob Eckstein cartoons:

Daily musings:

• Four Must-See Museums For Bibliophiles | LitHub

• Opinion by Bob Eckstein: No Local News Is Not Good News | Sun Sentinel

• Daily Cartoon Mon. Jan 1 | New Yorker

• Advice for an Untenable Situation cartoon | West Side Rag

• Website | BobEckstein.com

Etc.:

• 6/8’s Poconos Underground Comedy (and my birthday show + party) | EventBrite

• Find my NSFW comedy including a forthcoming new album here | OnlyFans

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