For 27 years, David O’Keefe worked for the Tampa Tribune. He started out driving trucks, but worked his way into the art department, eventually becoming the Special Projects Illustrator for the newsroom. In his time there, he gained national attention illustrating and sculpting for the likes of TIME, Sports Illustrated, Coca-Cola, and a publication near and dear to O’Keefe’s heart- Mad Magazine. Then, in 2007, he was let go by the Tribune, his 
services a luxury they could no longer support. But as is often the case, when one door closes, another opens up.
That door, for O’Keefe, can be found at his solo gallery on St. Armand’s Circle in Sarasota. O’Keefe’s work is displayed in the front window, a grisly looking Clint Eastwood from The Good, The Bad and The Ugly stares at me through the glass. Within moments of meeting David O’Keefe, I was stricken by just how ordinary he was. That is not meant as a slight. It’s just that when you look at his artwork, so vibrant and full of a personality that almost screams at you for attention, you almost expect the artist to be that way, too. O’Keefe however, is laid back, friendly and full of the wit that underlines his work.
Like most artist, O’Keefe dreads dealing with the business side of things. Luckily for him, he has the support of people who believe in his work, like business partner Wayne Curtiss, Chris Cinelli and Robb Makin over at Wall Art Gallery on St. Armand’s Circle and last, but certainly not least, Rena Charles, the Director of Gallery Relations for David O’Keefe Studios. Without them, O’Keefe says that none of this could have been possible.
A father of 4, O’Keefe resides in Brandon with his wife Janice. It was a little funny when we discovered we lived maybe 2 miles from each other, but we both drove to Sarasota for this interview. It was definitely worth the trip. To see some of his work, especially his sculptures, in person is a thrill. There are so many details to appreciate, like in the Godfather painting, with Francis Ford Coppola in the picture above the mantle. Genius!
We sit down for the interview in front of O’Keefe’s newest painting, an ensemble piece featuring the cast of Caddyshack to be unveiled at O’Keefe’s South Beach Miami gallery during the weekend of the big game. What followed was an hour and a half conversation about art, politics, bicycles and Jack the Ripper among other things. I did manage to get in a few questions.
David O’Keefe has found his calling beyond the world of editorial illustrations, and I get the feeling he wouldn’t have it any other way.
Ruben: I understand you realized you wanted to be an artist at an early age. Can you tell me how it started? Were you trained in art?
David O’Keefe: It all started with football. I loved football. At about 5 or 6, I started drawing football players. I still have a few of them. Even at an early age I enjoyed drawing lot’s of people. I used to draw the whole team running across the field. Then, I guess it evolved into drawing action scenes. I would draw the field goal being blocked. In between all this there was a lot of army men and WWII drawings. I remember drawing a good looking field goal block and the next one was a guy jumping on the other guy’s shoulders blocking the ball. The guy would get more and more elongated each time I drew it. Then I started drawing the whole team on both sides, with a logo. I loved drawing the logos. My dad saw I was always drawing. He was going to paint my room one day, and he let me paint on the walls, so I tried to do my army men and football players. I think that was my first mural. From that point on I was just always drawing.
So then, by the time I was like 8, I was drawing people and I drew my dad. I told him people keep moving around and he said “not everyone is just going to sit there and pose for you.” So he told me to draw Walter Cronkite on the news and so I had a half an hour to draw Walter Cronkite. They would go to stories, but it would always come back to Walter, so I got good at drawing Walter Cronkite and that was probably my first caricature type drawing. Then, when I was about 10 or 11 I got into doing caricatures events for Maas Bros. and I had my own cable access show called “DJ and His Magic Drawing Pad”. I’m getting more and more involved in caricatures and I am drawing O.J. Simpson and Dick Butkus. Popular stars of the 70’s. A lot of celebrities and sports figures. Just drawing people and having fun with it, I sort of knew that’s what I wanted to do. I had no formal training. In hindsight, I probably should have.
RJC: Who are some of your influences?
DOK: At an early age, it would be Norman Rockwell, my number one influence. I love the emotion, reaction, and interactions of his paintings. They are very warm. Other influences, Peter Paul Rubens. As far as humor, Mad Magazine.
RJC: What is your favorite piece of art not created by you?
DOK: Four Seasons of Love by Jean-Honore Fragonard at the Frick in New York. It is four individual pieces, but they count as one.
RJC: What is your favorite job that you’ve had?
DOK: My favorite job I ever had was doing movie storyboards. My kids really got me into animation and animators. People like Glen King at Disney and the guys over at Pixar. Those guys are awesome. That just seems like a lot of fun.
RJC: Do you tend to gravitate towards any one feature when starting a caricature?
DOK: Yeah, one thing I like when I do caricatures is I like to do groups of people. That way you can play one person off the nextperson. It’s always fun to do groups. When I do a caricature of a single person, I like to start off with video and sketch live. I like that it can look 3 dimensional and I like to think that everybody in my caricatures are real. You know, they could be real people in a 3Dmovie.
RJC: When did you start sculpting?
DOK: My first sculpture was for the Tampa Bay Rowdies(...the Rowdies arrrrre...A Kick in the Grass!), in the 80’s. I was a big soccer fan. I actually worked for them. I did caricatures in the stands.
RJC: How has the illustration world changed in the last few years?
DOK: It’s evolved into much more Photoshop stuff. Many of the illustrators I’ve known have switched over to Photoshop. The deadlines have gotten tighter because digital art allows for quicker turnaround. Back in the 90’s, I’d have 4 days. I would sculpt something, then the camera guy would come by and shoot the pictures in my bathtub and I’d mail them to New York over night. But it was the whole ‘no control’ thing. You couldn’t change anything. If you had a large crowd scene, you’d have to build ant paint the whole thing by hand.
RJC: What’s playing in your iPod?
DOK: The Beatles, John Vanderslice & Pernice Brothers
RJC: What’s the last good book you read?
DOK: “The Day I Died” by Steve Sjorgen. He’s a local guy.