Milt Klingensmith

Tell us: Who is Milt?

After graduating from Kendall College of Art & Design in ‘92, I worked in small, semi-underground comics and freelanced for magazines (Guitar, Rolling Stone, Money). An opening at the paper developed at the same time that I had a small show of my comics and illustration work. I invited the paper’s art director (and every other art director I could find in the phone book) to the opening via a postcard and I have been illustrating, designing and occasionally writing for them since.

At the start, I was illustrating whatever came in my direction. Later, I became the primary cover artist for our “Weekend” entertainment tab. After a number of years of that, I began working with the other sections again, illustrating and designing, while staying part of the “Weekend” tag team.
Now I’m at the paper, teaching at Kendall and freelancing.

Who are some of your influences?

The artists I’ve been influenced by have varied greatly and depend on the artistic direction I was exploring at the time. When I started out working solely in very blended pastel, Gary Kelly and Miguel Covarrubias were strong influences. Studying them taught me a great deal about design and composition. I would do small (3” x 3”) studies with a Sharpie of Kelly’s works, just to break down in simple terms the structure of his compositions.

Steve Brodner, Ralph Steadman, Alan Cober and, especially, painter Jack Levine were who I looked to when I began to loosen up and explore more spontaneous methods of working. I developed a technique on white scratchboard using sumi ink and litho crayons to try to emulate the feel of Levine’s printmaking.
When I was painting exclusively, it was Frank Schoonover for his incredible palette. I also became obsessed with pulp fiction painters of the ’50’s at that time. Being a newspaper artist, I had to paint very quickly, and their work has a feverishly executed feel to it while still looking masterful.

And some of your favorite illustrators?

I find I’m following the work of artists who work nothing like me. I’m always checking out Samuel Casal’s Web site to see what’s new, always floored by what he’s doing. Shino Arihara has a great painting style and is always inspiring.

Describe your environment and how you interact with the newsroom. Are you involved in planning? Do you attend meetings? How does the creative process unfold?
Before, the art department would just get an art request and do a rough layout to go with the resulting illustration. Now we’ve become more involved at the front end of the process: attending planning meetings and discussing visual possibilities for stories, whether that’s an illustration or finding a direction for the photography. It’s a newsroom undergoing a significant evolution, so the process hasn’t been ironed out completely, but it’s a welcome improvement to be more involved.

Take us from assignment/pitch to sketch to execution.

After hearing a description of the story, or in more ideal cases, after reading it, I’ll come up with a concept by running through thumbnails in my sketch book or brainstorming with one of the other illustrators. This is when I try to work the whole story down to just a sentence and come up with images and words associated with that idea. When I have a concept sketch, I decide which style would be the most appropriate. Once I have it under way, the presentation editor sees it and either signs off or makes some suggestions. When it’s finished, the PE gives the official stamp of approval and it’s handed off to the copy desk for the text to be set in.

I give them a page sketch from Freehand or Photoshop as a blueprint for how I plan the illustration and text to interact.

What about illustrating do you like most? The least?

The problem-solving nature of the job. Every day you have a visual problem thrown to you that you need to solve.
But more than that, I enjoy the freedom to mix techniques and push yourself in a direction you haven’t tried before. Surprising yourself with unexpected results is a hell of a feeling.

And, of course, the caricature. I live for the caricatures.

What illustration(s) are you most proud of?

I’m still pretty pleased with a painting I did for the play of “The Night of the Iguana” (see pg. 5) and a portrait of Martina McBride (pg. 7). The painting because I felt it captured the undercurrent of the storyline and did it in an unexpected and bizarre manner. The caricature because it was a big stride in the direction I wanted to go with my mixed-digital portraits. I spent a great deal of effort in designing it and stripping away what it didn’t need.

Some papers are very supportive of illustrations, some less — what about your paper?

We have a pretty hospitable environment. Our “Weekend” tab is an illustration of some form or another every week. Features and entertainment use a good deal of them. I’ve started doing some occasional caricatures for the editorial section. Hopefully, in the future, we’ll do more with the Issues/Opinions pages. So far, those have stayed as they have traditionally been: photo driven. I see friends at other papers doing some stellar work on these types of pages, and it’d be great to see that happen here.

As for A1, we’ve gotten to put illustration out there for centerpieces more and more. The “feel” of the style is very important though, and it usually is a “photo-painting” or a collage.

Any controversy over tone or taste?

I once did this group caricature of the Bare Naked Ladies. It was a Christmas Eve concert and I drew the guys with the bodies of bare naked ladies with strategically placed wreathes, presents and choir books. There was nothing obscene about it. Anything requiring a PG-13 rating was concealed, but it was, admittedly, a weird, gender-bent illustration. It had been approved by several editors before I started it. But after it was finished and going to press the night before it was to run, someone in the production process found it “blasphemous” and phone calls were made. It ended with the a new round of talks and the plug was pulled on it. I had to create a new cover on the fly.
That was early in my career at the paper. I was learning what they were willing to try, how far I could push and what ills were worth pushing for. Today, I doubt that I would have bothered with this image and would have chose to push some other envelope. Looking back, I see it as not worth the storm it started.

Share a piece of advice with a young illustrator aspiring to work in editorial illustration. Is there anything you would change in your career?

Always boil it down (the story) to a single sentence. Get to the heart of what the article is about and then start coming up with images based on that. That’s not always easy, since not every story that comes to you will be that worked out and focused. But that’s your ideal starting point.
And diversify. When I started at the paper, I was a freelancer with one main style. I eventually started working in a number of techniques, which makes you more valuable to the paper. But it also gives you more options in solving problems and helps keep you from burning out as easily.

About Tyson Evans

Tyson Evans served as SND’s President in 2018 and is a member of The Society’s executive committee. He is a senior editor for strategy and product at The New York Times.