Yogi Berra once said, “Neil has taken some of the greatest photos you’ll ever see, even if you’ve seen them before.” Neil Leifer has shot 16 Olympic Games, 15 Kentucky Derbys, the first 12 Super Bowls and four World Cups. He’s lost track of how many World Series and heavyweight title fights, but knows 35 of them are Muhammed Ali’s. He is most famous for his shot of Ali jeering over a prostrate Sonny Liston, beckoning him to rise—one of the most legendary photographs ever—and his overhead snap of Ali with his arms raised in victory above a knocked out Cleveland Williams in 1966, both of which were featured heavily in the recent coverage of the champ’s death. But even before that, Leifer was best known for his football photography, which has been compiled in the recently released Golden Age of American Football. We interviewed the legend in honor of both the book and his current exhibition at the Peter Fetterman Gallery in Chicago, Playboy’s original hometown.

You grew up on New York’s Lower East Side when it was a rough area. How did you get started in photography?
It was a hobby at first. I started when I was 12 or 13; it must’ve been 1955. The Henry Street Settlement, this community center that’s still around near the low-income apartments where I grew up, had a camera club, just to keep kids off the street. Life magazine provided the film. I was a huge sports fan—the Brooklyn Dodgers, New York Giants—but I couldn’t afford tickets, especially not good ones, so the idea that someone would not only give me the best seat but pay me was a joke. If I went to Yankee Stadium, it was gonna be in the nosebleeds; not in front of the dugout or on the field. I thought I should be paying them.

Neil Leifer: The Golden Age of American Football, $50

It was your 16th birthday when you took the picture in the book of Alan Ameche’s sudden-death touchdown in the 1958 NFL Championship Game at Yankee Stadium, aka the “Greatest Game Ever Played.” Where does it rank in your cannon?
Well, I’m better known for the Ali vs. Liston photo, and that’s in my top 10, and more likely my top 5. My shot of Secretariat is up there, but my shot of Ali vs. Williams is the only one where I don’t know if I would change anything. Every other one, including the Ameche shot, there’s small things I see that I would change. That’s what motivates you to come back for the next assignment. But the Ali vs. Williams one was preconceived and executed perfectly. [laughs] I never met a modest photographer that was any good—you need a healthy ego. And luck, you can’t discount luck. My job was not to miss—and that’s what separates the good from the great.

You’ve spent time with both Ali and Fidel Castro, who was famously snapped lighting your cigar. Who was the more dynamic presence?
Don’t forget I’ve photographed Ronald Reagan—I like to say I’ve photographed everyone from Charles Manson to the Pope. But in terms of subjects, no one comes close to Ali. Personally and culturally he was the best-known person on the planet, and not because everyone was into boxing. But there are people who love the camera, and Fidel Castro loved the camera—and it had nothing to do with looks! Another one was Ed Koch, who could never be confused with Brad Pitt but you turned the camera on him and he had a visual charisma—same as Castro, Reagan, Pope John Paul.

What are you currently working on?
Well I’ve got another book out now, Relentless, that’s got shots of Mickey Mantle, Arthur Ashe, Sugar Ray Robinson, Joe Namath and Arnold Palmer. And I’m working on The Fight, where my photographs will accompany Norman Mailer’s coverage of the Rumble in the Jungle, which originated as two-part story in none other than Playboy.