In Madonna: Confessions, Guy Oseary, the star’s manager and friend for 18 years, photographs her 2006 world tour.

You’re not a professional photographer. What made you decide to photograph the tour?

I always loved taking photos. I always have a camera around snapping away. But when my girlfriend gave me a professional camera, I told her, “I wouldn’t mind taking some photos while I’m on tour for the next four—five months,” the way you sometimes say, “I’m going to learn five languages or I’m going to start working out.” I thought I’d shoot a few shows [there were 60]. In fact, I shot them all... actually I missed one.

What’s it like being on tour with Madonna?

It’s such a massive tour and such an elaborate show—trucks and headsets and lighting and costumes and video equipment. Also, it’s thrilling to watch your friend put it all together, to see where the seed of an idea ends and how people react to it.

What was it like photographing the tour?

I still had my day job, so I ended up running around all day and then running around all night taking photos. The show had so many levels that sometimes the only way to see it was through a camera. I was trying to capture everything. I’d go from right to left to center, always looking for a different perspective. Some shows were outdoors, some in theaters or stadiums, and the fans change, the energy changes. I took over 50,000 photos. [Madonna chose which ones would appear in the book.]

The book seems more like an art book than a chronicle. Was that intentional?

Confessions was art directed by Giovanni Bianco. He created the style for the tour, and it was repeated on everything, the album cover, the posters. Giovanni saw it all as one piece particular to this tour, and he brought that element to the book.

How did you get together with Madonna?

That’s a long, long story. Basically, I was working at what was to become Maverick Records in 1991, and we became friends, and it just continued on.

You were just a kid—17 or 18 years old?

I prefer to say “little man.”

And what’s next?

The Sticky and Sweet tour. First stop: Cardiff, Wales. I’m going to photograph it, but gently this time. I’ll just shoot here and there. There’s too much going on.

And what about Madonna’s brother Christopher Ciccone’s book, Life with My Sister Madonna?

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