Dittmar, who grew up in western Connecticut and attended New York University, began shooting notable people while on assignment for The Washington Post in 2013. He has shot more than 100 famous people since, usually using his trusty Hasselblad. He likes that his subjects notice the camera and ask questions about it. Dittmar adds: “It changes the mood of the shoot and elevates it to something special.”
In his blog, he writes: “You have to forget you’re a fan. After you do that, you can learn a lot, like Tom Hanks is a doting grandfather who collects typewriters, Patti Smith hand writes thank you notes … ” In the book, Dittmar pairs the two because their forms “create a visual leaning together, a new, interesting overall shape.” He also likes that their personalities and cultural significance play off each other. He pairs two very different portraits of Lily Tomlin, showing the “range of her personality in both an amazing stare and a genuine laugh.”
As a teenager, Dittmar immersed himself in the books of famous portrait photographers like Annie Leibowitz, Martin Schoeller and Richard Avedon, while visiting his local Barnes & Noble. Then, like many budding photographers, he worked as a photographer’s assistant after college. Not many, however, get the chance to do so for some of their idols, as Dittmar did.
Dittmar shot portraits of Martina Arroyo for The Washington Post in 2013, and he describes her as “the quintessential word of diva in her own day. She was a famous opera singer, significant in pop culture, and now an elegant retired woman, who is still so vibrant and beautiful, and I felt like Lupita [Nyong’o] might be going along a similar path.”
Dittmar listens to music during shoots as a way to connect to his subjects and control the atmosphere. In the book, he refers to music as a common denominator and writes: “I bring music to every shoot. … Not everyone loves the same music, but everyone loves music. It’s a human thing, and I’m interested in humans. I love asking questions. I love shaking hands, looking someone in the eye, and getting a sense of what they’re all about.”
As the opening image of “two,” this portrait of Sting is one of Dittmar’s favorites. He says, “His music is so intertwined with, so fused to my life … it was a just a mountain to put aside [to be able to focus on shooting].”
Dittmar often plays Al Green’s music during shoots. He writes: “Occasionally I get nervous that Al’s lyrics can get a little too smooth for someone I’ve never met. Then “Love and Happiness” plays and that song is too good to worry about excessive smoothness. When we photographed [him] in Memphis, I got him singing and had a hard time getting him to stop.”
Dittmar pairs portraits of Billy Joel and Vanessa Hudgens, who played the title role in the revival of “Gigi” on Broadway, to suggest a juxtaposition of types of musical theater — old and new New York.
Of Aziz Ansari, Dittmar says: “I just saw him at Madison Square Garden. … That happens to me all the time, where I’ll see someone [performing] somewhere and then I’ll get the call. … I really love photographing people, then seeing their stuff because I get a sense for what they’re all about — and then I get to see how they’re different from their work. That was certainly the case with him.”
He pairs Mika Brezenzinski’s portrait with that of Serena Williams as “two strong feminist beings. … They’re so different, but strong individuals that had a powerful presence.”
Paired for their similar gestures, the portraits of Cuba Gooding Jr. and Michelle Dockery were shot most recently and the last grouping in the book. Ending the book with these portraits seemed to Dittmar like the “perfect punctuation mark.”