Tony Bennett

Tony Bennett, Toronto, May 1993

TONY BENNETT WAS ALWAYS ON THE LIST. I didn't end up photographing most of the people on my list, but in 1993, when I might have described my career as "up and coming," I could still imagine that I'd get access to them one day. So I was pretty thrilled when the chance to do Bennett's portrait came up. I only wish I knew who gave me the assignment, if anyone did; there's nothing in the Big Ledger, so there's every chance that this was something I begged and scrounged into happening, and that these photos might never have been published anywhere until now.

I had photographed Bennett once before, for NOW magazine, live in concert at the old Ontario Place Forum (long since demolished.) I was already a big fan then, thanks to the Jazz compilation Columbia had put out a couple of years previous, when Bennett had re-signed to his original record company after years of struggling with money and drugs. I got a couple of decent shots of Bennett with Ralph Sharon's trio, working the crowd all around him like a pro, and assumed that would be the closest I'd ever get to the man.

Tony Bennett, Ontario Place Forum, Toronto, August 1989

The List was the informal wish list of portrait subjects Chris Buck and I had challenged each other to come up with in the late '80s, sitting around the table in a Chinatown restaurant before he moved to New York City. We didn't imagine we'd have a shot at most of the people on our lists when we were begging for access to bands still playing clubs or counterculture figures passing through town. We had a few names in common, and I think Chris ended up getting quite a few names on his list, but neither of us ever got a portrait of Sinatra.

Bennett was in town doing a benefit for the Variety Club, that much I do know. (His willingness to do charity gigs had long ago earned him the nickname "Tony Benefit.") I'm pretty sure that legendary old school local promoter Gino Empry was present when I took these photos, and though I can't exactly remember where I found this little patch of flattering window light in some uncluttered corner, a tiny stirring of memory is telling me it might have been at the King Edward Hotel downtown.

Tony Bennett, Toronto, May 1993

I loved Bennett's singing. I'd grown up with "I Left My Heart in San Francisco" thanks to the MOR AM radio stations my mom listened to, but when my then-girlfriend was sent a copy of the Jazz compilation to review, I became a huge fan. Years later I'd fall big time for a string of records he released in the late '50s and early '60s (The Beat of My Heart, Tony Sings for Two, I Wanna Be Around, Who Can I Turn To?, If I Ruled The World: Songs For The Jet Set, the records with Count Basie) during the last golden age of the crooner.

The shot above reminds me of the single moment I do recall, when Bennett looked at me through the camera lens and said "Aren't you a bit close?" I don't think he was the first portrait subject to ask me that question, but he's definitely the first one I distinctly remember. I already knew by this point that getting up close to my subjects with a relatively short lens was my best chance to elicit some sense of intimacy in the scant minute - sometimes just a few dozen seconds - I had for these shoots. One day I need to come up with a snappy answer.

Tony Bennett, Toronto, May 1993

After somehow managing to get the access to take these shots, I spent years trying to figure out what to do with them. As long as Bennett remained famous - he is still singing, and still famous, to this day, thanks to a string of duets records he started making in the early 2000s - I knew I had to get them into my portfolio. But anxiety and a typical lack of self-confidence meant that I could never choose the right shot or figure out how to print them the right way. I've revisited this shoot many times, but least two of the frames here are ones that I've never printed before.

The frame at the bottom is my favorite now, a little moment near the end of the shoot when Bennett was probably wondering when his handlers were going to extricate him from my looming camera. Considering that this was probably a shoot that had more to do with begging than an assignment, I can still read the wariness in Bennett's face in most of the shots. And twenty-five years after I shot them, I think I finally figured out how to print them right.