Howard Stern Talks About Painting and His July 16 Dan's Cover

Legendary radio host Howard Stern returns to the cover of Dan’s Papers after his debut cover in December. The longtime Hamptons resident discusses his process for realistically recreating the beauty of the area, the great masters who inspire him and more.

What is the name of this magnificent piece, and what’s the inspiration behind this loving recreation of Deerfield Road?

Thank you. I’m glad you like it. It’s just Deerfield Road. Sweet and simple. I was driving around and was attracted to everything about this spot. The way the light breaks out behind the bushes and onto the field was special. It had everything—mounds of dirt—grass that had spots with the road coming through, a variety of bushes and trees. Loved the wide empty space but in the far distance those homes are creeping in.

I imagine one day that this field might be filled in with lots of homes, so I wanted to preserve it. I took quite a few photos that day and had them laying around for a long time. Occasionally, I’d pull them out and think about turning them into a painting. Finally got the inspiration to begin this large view.

Did the conception and creation process of this piece differ at all from your usual process?

Yes. Typically, I do a very detailed drawing and then paint over it. I like the way the graphite mixes with the paint. With this one, I had difficulty drawing it and did a rather mediocre job of it. In my frustration, I began to just start the painting process prematurely. I don’t usually do that. It was not going well, so I put it away for a year and came back to it when I had more of a grasp on how to approach it. It kept nagging at me that I had given up, so I went back to it.

I started drawing over some of the portions I had painted already and, for sure, that’s something I had never done before. Once the drawing was complete, I painted over it and finished it. Not an approach I recommend, but for me, it was ultimately satisfying because I saw it through. This was an exercise in determination.

How do you achieve the level of detail and realism found in your works?

Detail and realism are what I’m attracted to. I have learned the foundation of my skills through the study of select great past masters like Friedrich, Bonington, Fragonard, Lusieri and John Ruskin—Ruskin was all about observation and detail. There are a number of contemporary masters I admire. I love the unbelievable work of Frederick Brosen, who is also my friend and teacher. On Instagram, I’ve discovered Dina Brodsky, Rod Penner, Terry Elkins, Greg DiNapoli, Bennett Vadnais, Lewis Chamberlain, and they are a constant inspiration.

I don’t paint until the drawing reflects as much detail as I can achieve and then attempt the same level of care with color. All of this comes down to technique, and I constantly work at learning more and more.

What makes this piece such an ideal fit for the cover of Dan’s Papers?

Seems to me it honors the beauty of the Hamptons. We’ve all seen this type of view out here and sometimes we pass right by it. I think the job of a good artist is to take a moment that most people would see as ordinary and turn it into something extraordinary.

With so much beauty to be found on the East End, how do you decide which vistas and locales move to the top of your painting list?

I photograph so many spots and just constantly review them until I land on something that inspires me. I better really love the photo because it takes me a long time to complete these. I’ve been busy drawing during the pandemic. I decided to exclusively draw for six months and not paint. I ended up with one large drawing of a scene in Central Park and two beach scenes in the Hamptons. Now for the next few months I will apply watercolor.

So, it’s Central Park and the beach for a while. I’ll be working on them for the next few months. Because of my job on the radio, I can’t paint every day, so these tend to take a much longer time.

And what’s next on that list?

I was thinking of going into Sag Harbor and taking a few photos. I think there might be a bunch of interesting paintings that will eventually come out of it.

Now that many of last year’s state restrictions have been lifted, which Hamptons venues, restaurants or other locales are you most excited to revisit?

I’ve been moving slower than most when it comes to returning to civilization, so not much to report on that front.

What do you find most rewarding about creating art?

It’s not an easy question to answer. I enjoy taking something ordinary and turning it into something that evokes emotion. My wife was looking at one of my landscape paintings and loved it. I said we pass that spot every day. She said that she hadn’t noticed it. That’s what I’m looking for—turning the overlooked scene and making it into something beautiful. I’ve always looked at radio as a blank canvas with all of that dead air waiting to be filled. It’s all art.

Where can fans of your work find it in the coming weeks, both online and up close?

Most of the stuff I do, I don’t share. At this point I don’t want to be evaluated. That could change. I’ve only been painting for seven years. Having said that, doing the cover of Dan’s Papers is a way to begin the process of showing people these paintings. I occasionally play with idea of doing a show in one of the galleries for our animal rescue charity, but I would need time to put that together.

Is there anything else you’d like to add?

Yes, Baba Booey to you all. Listen to SiriusXM. It’s really great.