We had the good fortune of connecting with Jeff York and we’ve shared our conversation below.

Hi Jeff, what was your thought process behind starting your own business?
I have always enjoyed cartooning and caricaturing and made decent “walking around” money doing so for the likes of Playboy, W magazine, and the Chicago Tribune. Additionally, I’ve always drawn gifts for family and friends as well over the years. One day, I figured I might as well give cartooning and caricaturing more of a go so I started to advertised my services on various social media platforms and develop a JeffYorkCaricatures.com website. It seemed like a good idea, especially considering my main business is advertising. Get more business by advertising – – who’d have thunk it?

Alright, so let’s move onto what keeps you busy professionally?

I think my caricatures are appealing to those looking for something unique or arresting for their articles online or in print, and I’ve always gotten hired by those who are looking to add a special flair to their prose be it online or in books. (I’ve illustrated for hundreds of periodicals and six books thus far.)  And yes, I still do personal commissions, family portraits, Christmas cards, etc.

 My caricature work in particular tends to be very eye-catching to most people because they go beyond just being good likenesses. They capture more of the person’s genuine essence. It helps that I’ve always been a bit of a performer through the years. I’ve acted some, sang, and done some standup. I’m also a natural mimic who can do hundreds of imitations. All that helps me truly see the subjects I ‘cartoon’, if you will, and get them enough to translate them to the page in line drawings. I think people like my caricatures too because they’re not grotesque. They’re more celebratory.
Additionally, working in black and white stands out in a very colorful world. Line drawings often have an elegance to them as well. Plus, I grew up on Mad magazine which was in black and white when I was a kid. And in my teen years, I discovered Al Hirschfeld at the New York Times and drawing in black and white just made such an impression on me.

As for what I hope my work achieves, I truly strive to capture the personality of someone. I like to caricature full bodies too as I believe that truly captures someone more than just drawing a facial portrait. Again, it’s about capturing someone’s essence and I think that comes through more with body language. The best compliment I ever get for my caricature work is when someone tells me that they can “hear” my subject from my illustration. I love that!

Let’s say your best friend was visiting the area and you wanted to show them the best time ever. Where would you take them? Give us a little itinerary – say it was a week long trip, where would you eat, drink, visit, hang out, etc.
Chicago has almost too much to offer; it’s a big sports town and an incredibly rick, cultural hun. How many cities could give the world both Michael Jordan and Georg Solti? Sure, the museums, the theaters, the CSO, or the opera house, and tony places like that are easy to suggest for fun, as are our sports arena, but there are humbler places that say just as much about the Windy City as those places. Local bars, the lakefront, mom & pop restaurants, the parks – there’s so much to take in that doesn’t cost an arm and a leg.   I love visiting the various college communities too, like Northwestern in Evanston, that’s a favorite. I like the high-end steakhouses in town like Gibson’s or Gene & Georgetti’s, of course, but I love the smaller, more intimate restaurants that have been around for decades too like Club Lago, Sayat Nova, or La Scarola. Great food, fantastic people watching there! I’d also advise a friend or anyone to visit the Windy City during autumn. The drive up the eastern coast along Lake Shore Drive and beyond all the way up to Lake Forest is a feast of color. I know, I know, ironic for a guy who caricatures in black and white.

The Shoutout series is all about recognizing that our success and where we are in life is at least somewhat thanks to the efforts, support, mentorship, love and encouragement of others. So is there someone that you want to dedicate your shoutout to?
I’d love to dedicate my shoutout to the memory of my twin brother Greg who tragically died of AIDS back in the 90s. He was my best friend, greatest muse, and toughest critic. And he loved my caricatures and encouraged me to draw more of them.

Website: jeffyorkcaricatures.com, theestablishingshot.org (my film review site), ChicagoIndieCritics.org

Instagram: JeffYorkCaricatures and JeffYorkChicago

Linkedin: https://www.linkedin.com/in/jeff-york-1a46404/

Twitter: @JeffYorkWriter

Other: theestablishingshot.org (my movie site with my reviews and caricatures) ChicagoIndieCritics.org (my film critics group) PipelineArtists.com (where I write essays about film and illustrate them too)

Image Credits
Jeff York (copyright 2012-2022)

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