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.

Barcelona

Barcelona, Summer 1998

I WAS IN MY MID-THIRTIES BEFORE I CROSSED THE ATLANTIC. Travel for pleasure was always out of reach for me; for most of my life I'd lived on a tight budget that prevented me from having one thing I really wanted (a car) and something I never knew I'd enjoy (travel.) At a life-changing point in my life, however, I found myself on a plane heading to Europe twice in less than a year. The first flight was to London. The second to a Spanish city I never thought I'd visit.

What happened was that on the night I met the woman who'd become my wife, she told me that she was going to Barcelona for a teaching gig that summer. She asked me if I wanted to come along. Of course I said yes.

Barcelona, Summer 1998

We were already living together by the time I landed at El Prat, where I was met by John Stone, an old friend of hers and a professor at the university, who'd got her the gig teaching editing to English students. He dropped me off at the little hotel where she was staying by the Plaça del Pi; I had a nap to ward off the jet lag before she came back from her class at the university, and fell asleep with the sounds of waiters clearing away lunch from the cafes in the square outside our window.

I was, to be frank, more than a little overwhelmed. I'd done a lot of reading about the city's history and architecture and re-watched a favorite film set there, but it was still dizzying to be in a place that - to my very Canadian eyes - seemed so ancient. There are plenty of places in Europe older, of course, and London is roughly the same age, but it didn't feel so antique, mostly because I'd stayed in Notting Hill when I was there. We were in the middle of the Gothic Quarter for much of our time in Barcelona, and I was transfixed by the churches, the weathered stone and the tiny, medieval streets.

When K was off teaching classes, I'd head out with my cameras and wander. I was always caught short when I turned a corner into a tiny square with an elaborate fountain in the centre, or a stretch of harbourside road laid out in the city's prosperous days in the late 19th century. There was nothing like this at home, and I was in full bumpkin mode, snapping photos just to try and remember what I had seen.

Barcelona, Summer 1998

I was very much a tourist, and it felt like a luxury. We didn't leave the city once during the nearly two weeks I stayed there with K, and barely left the Gothic Quarter, the Rambla or El Raval, where John and his wife Rosa lived. We spent hours in the Boqueria, the old city market, and made just one quick jaunt up to Gaudi's Sagrada Familia, but for some reason I didn't take a single frame. There was so much to see, and I still don't feel like we scratched the surface.

It was a trip I still remember fondly, and K and I keep promising each other we'll return one day. It left me with an urge to travel that I'd never had before and still haven't been able to shake. As for the photos - they're OK. If they seem like random snapshots taken in a daze, it's because they were. One day maybe I'll get a chance to take better ones.

Film festival, again

Judy Greer, Toronto, Sept. 2017

GOING THROUGH MY FILM FESTIVAL SHOOTS AGAIN, I found a few shots that I missed the first and second time around. It's rewarding to find some more decent portraits, of course, but it's also a bit depressing, since I enjoy doing this kind of work so much, and I do it so rarely these days.

It's hard to find standout frames in a portrait shoot. At first you might be looking for the most flattering shot, but it takes a few more passes to see the shots where something revealing is happening in your subject's expression, or the frame where they've relaxed just enough to let an interesting mood or the trace of a thought - whether it's anxiety or impatience or whatever - read in their features.

Jessie Buckley, Toronto, Sept. 2017

Ed Oxenbould, Toronto, Sept. 2017

Cedric the Entertainer, Toronto, Sept. 2017

The Judy Greer shot, at top, might be the moment when she let her discomfort with how closely I was shooting register. In any case, it works as a portrait of an actress with a comic gift. The Cedric the Entertainer shot is at least most of the way to what I was trying to get with a portrait of a comedian that was more intense than funny. (Most comedians have, at the core of their character, a kind of anxious discomfort that's anything but humorous.)

Anneke Sluiters, Toronto, Sept. 2017

Ksenia Solo, Toronto, Sept. 2017

Anneke Sluiters was fully intense for nearly every frame of my shoot with her. I processed the first frame I chose from that shoot to highlight her performance rather than something flattering. She apparently didn't like that, and complained to her publicist, so I took that shot down. I think this one strikes a decent balance between the two.

I got a performance of a different kind from Ksenia Solo - something more like a film noir heroine (or femme fatale.) When you shoot pretty people - and women, especially - the temptation to slide into mere glamour photography is tempting. Some clients (and subjects) want glamour photography, but it's never really satisfying to go over contact sheets (or digital files) and find nothing more than that, so it's best to gently push for a bit more all the time.

These are issues that I used to agonize over all the time. Getting a chance to shoot portraits again, I realize how much I actually missed that agonizing.

Vince Vaughn

Vince Vaughn, Toronto, Sept. 1998

THE BEST - AND WORST - THING ABOUT PHOTOGRAPHING ACTORS is the likelihood that you will be confronting their persona before you get a glimpse of the real person. It's a gift if you don't have a lot of time for a shoot or if the client you're shooting for isn't expecting more than that public personality on their pages. But it's an obstacle when you're aiming for something a bit more interesting or revealing.

Some actors are willing to let you see that, either because they're young and still developing that persona, or older and bored with it. There's nothing wrong with actors and their personas - the profession in general and Hollywood in particular are built on performers who can deliver some unique variation on a character convincingly.

Nearly every major star has refined their persona carefully, and the golden age of Hollywood is a gallery of indelible characters who marketed their onscreen personas to a receptive audience: Bogart, Garbo, Stewart, Gable, Wayne, Hepburn. Cary Grant, an actor whose persona was vividly drawn, famously admitted that it existed in a realm utterly separate from Archie Leach, the mere mortal born in Bristol to an alcoholic father and a depressive mother: "Everyone wants to be Cary Grant - even I want to be Cary Grant."

Vince Vaughn, Toronto, Sept. 1998

Vince Vaughn was at the film festival promoting his role as Norman Bates in Gus Van Sant's (wholly unnecessary) remake of Psycho when I photographed him for NOW magazine. As a result, I was confronted with a combination of Bates and the slightly comic lounge lizard he had built his budding stardom on in the movie Swingers a few years previous.

I can tell immediately that I shot this on the balcony of one of the suites in the old Four Seasons in Yorkville - the same place where I'd done the Ally Sheedy shoot earlier that year. I knew within a couple of shots that Vaughn was delivering the "looks" he had on call, and moved him around every few frames to try and shake them loose - to little avail.

Vince Vaughn, Toronto, Sept. 1998

The closest I got to something a bit different is the middle shot, where I fit his very tall frame into the square viewfinder of my Rollei. Apart from that, I got some Norman Bates (top photo) and a bit of the ladies' man (bottom photo.) I'd barely gotten through half of my second roll before Vaughn got up from the chair and began leaving the room, with a sort of half apology that felt like I was in one of his films: "Thanks, bro. That was great. Yo, bro, I gotta get going. Thanks a lot, bro."

John Boorman

John Boorman, Toronto, Sept. 1998

AS I'VE SAID BEFORE, SHOOTING MOVIE DIRECTORS is often more interesting than shooting actors. Actors make a living being seen and photographed, which should make them more relaxed in front of a camera, but that usually isn't the case. I've found that most actors have an uneasy relationship with photographers and their cameras, especially when shoots only last a few minutes and preclude any possibility of collaborating or controlling the outcome.

Directors, on the other hand, are usually more than aware of how cameras work, and how much control you are actually giving up by consenting to be photographed. Perhaps it's because they're usually on the controlling end that they seem more relaxed in portrait sessions; I sometimes imagine that they're thinking that turnabout is fair play, after all, and that something unexpected might come out of it all.

John Boorman, Toronto, Sept. 1998

I couldn't tell you if any of these thoughts were in John Boorman's mind when I took his photo at the film festival, where he was promoting The General, a film about a real-life Dublin gangster who met a sticky end when he double-crossed the IRA. The most I remember about this shoot nearly twenty years later is that I used the back of a box spring as a backdrop in the hotel room where I shot.

Boorman was a bit of a legend, at least to me, when I did his portrait. His films were a puzzling and fascinating mixture of genres, and his career was the polar opposite of a journeyman director. From the bleak, sun-drenched noir of Point Blank to the nightmarish Deliverance to the utter batshit strangeness of Zardoz, he was a director who seemed intent on typecasting himself. He was obviously drawn to edgy and difficult stories, but his most autobiographical film - Hope and Glory - manages to be warm without excessive sentimentality, even though it's about his own childhood.

John Boorman, Toronto, Sept. 1998

I didn't do much to push him - I was frankly a little in awe - but two decades on my favorite shot is the one in the middle, which I probably wouldn't have printed for the paper in anticipation that they'd never have run it. It's one of those "between" moments that I'd come to cherish more with time, a brief glimpse of a subject less intent on the camera.

Sometimes these moments can be revealing, or present someone with an intriguing awkwardness (my friend Chris Buck has made a career out of trying to elicit these moments) but when you're looking for them, it's often difficult to stay on the right side of the line between interesting and banal.

Eight years later, I'd end up shooting Boorman's son Charley for the free national daily. His father had cast him as the lead in The Emerald Forest, but Charley had begun pursing a career as an adventure filmmaker, with documentaries about epic journeys and harrowing endurance races on motorcycles.

Charley Boorman, Toronto, Dec. 2006

I'm not sure, but I think Charley Boorman was in Toronto to promote his latest adventure with his bike pal Ewan McGregor, or a TV series documenting the Paris-Dakar race he'd done earlier that year. I like to think that I caught a bit of his daredevil image in my very brief hotel room shoot with him. I'm pretty sure I would have mentioned my shoot with his father several years earlier, but his reaction - likely polite, probably nothing he hadn't heard before - is lost to my memory.

Sally

Sally Lee, film test, Parkdale, April 1991. Kodak VPS rated at ISO 20, pushed 1 stop, 30R filter

MY RECENT POST OF OLD FASHION PHOTOS featured some shots of Sally Lee, my onetime roommate in the Parkdale loft and sometime model for my studio experiments. When I was scanning those shots, I remembered that one of the thankless favours I asked of Sally was being the model for my attempts to calibrate the results of cross processing colour negative film through E-6 chemistry.

While it's true that Sally was a convenient model, living as she did in the next room, I'd be lying if I didn't admit that I knew that scrutinizing rolls of slide film for contrast and tonal shifts would be generally more pleasant with an attractive model. She was agreeable enough to stand in front of one of my strobe lights for two sessions in the spring of 1991, holding up my homemade colour chart while I changed filters and made notes on f-stops as I worked.

Sally Lee, film test, Parkdale, April 1991. Kodak VHC rated at ISO 20, pushed 1 stop, 40M filter

Sally Lee, film test, Parkdale, April 1991. Fujicolor 400 rated at ISO 50, pushed 1 stop, 40M filter open 1 stop

I'd first seen cross-processed photos in American music magazines, in work by people like Michael Lavine. Not long after my predecessor at NOW magazine, photographer Chris Nicholls, had done some early work with cross-processed slide film, and he was kind enough to sit down with Chris Buck and I in an east end diner and give us some basic tips on how it was done.

He said that you could cross-process both ways, but that you needed to do a lot of testing to see how pushing and filters and exposure would effect the results, especially when working with colour negative film. After some early success with slide film-turned-negative, I picked up a variety of negative films and tried to find something workable. I carefully recorded my results and offered them to anyone who wanted to try it out, figuring that it was better to share information than hoard it.

In the end, negative-through-slide cross-processing turned out to be too unpredictable to work with, though I'd keep going back to slide-through-negative cross-processing on and off for the next decade, looking for a way to get punchier colours and interesting historical effects. Nowadays almost all of this can be approximated roughly in Photoshop, though to my eye there's always something specific and unique to film chemistry - some peculiarity in the tonal shifts - that no one has ever been able to recreate digitally.

Sally Lee, film test, Parkdale, April 1991. Fuji Reala rated at ISO 12, 85 filter

Sally Lee, film test, Parkdale, April 1991. Kodak Ektar 25 rated at ISO 3, pushed 1 stop, no filter, closed 1 stop

Sally Lee, film test, Parkdale, April 1991. Agfa Portrait 160 rated at ISO 20, 85 filter closed 1 stop

How I ended up living with Sally is another story. She was, by the time I took these shots, my ex-girlfriend's sister, or very nearly. The three of us had moved into the Parkdale loft together, subletting the space against the wishes of a rogue landlord who tried to force all the tenants out with intimidation and threats. Sally's sister broke up with me after moving to New York City to study, leaving us in a somewhat awkward living situation.

We lasted a year after the breakup as roommates before it got all too much for Sally and she moved out. I was so desperate to have a shooting space that I was apparently willing to endure thug superintendents shoving toothpicks in my door lock, writing threats on our door and blaring country radio in the empty unit next door, along with the emotional awkwardness of living with the sister of my ex, as nice as she could be. I'd end up living in that loft for the rest of the decade, though the landlord and his thugs were gone not long after I took these photos.

Sally's essential likability has always made her popular in Toronto's overlapping worlds of art, music and film, where she's worked since we were roommates. I've always felt that I must have tested her amiability with my own basically grouchy temperament, not to mention my increasingly fragile emotional state during and after the break-up with her sister, but we've somehow managed to stay friendly in spite of it all. She took up the bass while we were living together, and she's till at it today, playing with our old upstairs neighbour Don Pyle in a new band. I'd like to post these old photos as a belated thank you, both for helping me out and for enduring.

Jason Patric

Jason Patric, Toronto, Sept. 1998

1998 WAS A VERY BIG YEAR FOR ME. I didn't have any major career breakthrough - quite the opposite - but it was the year when I met the woman who would become my wife. I had begun the year in London, England, and by the time the summer rolled around I had flown across the ocean again to visit my new girlfriend in Barcelona, where she had a teaching gig.

A year that began with what felt like a tipping point had definitely delivered on transformation. In hindsight, I'm tempted to scrutinize the work I did that year for signs of change. It's a lot of weight to put on shoots like this one of actor Jason Patric, shot at the film festival as a cover for NOW magazine.

Jason Patric, Toronto, Sept. 1998

Patric was becoming a leading man when I took these photos - an attractive actor in his early '30s who had gone from the vampire bro flick The Lost Boys to playing Lord Byron and a junkie narcotics detective. He'd been gossip fodder when Julia Roberts, at the peak of her "America's Sweetheart" fame, rebounded on to him after jilting his Lost Boys co-star Kiefer Sutherland at the altar.

As with my Ally Sheedy shoot, I'd returned to cross-processed slide film to try and extract as much saturation as possible from colour film. I could control the process just enough by now, and was looking to get the look of Kodachrome film, with its bright primaries and nearly plastic skin tones, as it often appeared in old magazines and the chromolithography that rendered colour photos almost like hand-coloured stills. An esoteric goal, to be sure.

Jason Patric, Toronto, Sept. 1998

I barely said a word to my subjects; having found the sweet spot of light - or, as in the case of this shoot, having created it with a high strobe light bounced into an umbrella - I gave only the barest of instructions (lean into the wall, look right, don't smile) and peered into the viewfinder until something registered in their eyes. I'd spent a decade desperately searching for a style; by this point, I decided to stop trying and pare away almost everything from around my subject. No complicated lighting, no backdrops, no pre-visualization.

Maybe I was inspired. Maybe I was just tired. Perhaps being in a relationship again after many years as a lonely single man had restored some confidence, or perhaps it had given me a healthy distraction from constant, anxious fretting over my creative direction. Nearly twenty years on, I look at these photos and can only imagine myself saying "Here are some photos of what Jason Patric, actor, looked like in this hotel room at this moment in time. Take from this what you will." I was either very secure about my work or simply beyond caring about making something photo editors might have wanted to see.

I'm not sure what happened to Patric's career after this. In the film he was promoting - Neil LaBute's Your Friends and Neighbours - he'd played a very convincing heavy, a sociopath who plays a major part in destroying the marriages of two couples. Perhaps he'd done his job too well, or perhaps he was simply too handsome, but he never became the leading man it was assumed he was going to be. Perhaps that was never his goal, as he's built a career since then playing anti-heroes, sadists, cops and untrustworthy authority figures. I won't lie and say that I don't wish he'd become a matinee idol, but I still like these very minimal portraits of a cypher-like subject.

Ally Sheedy

Ally Sheedy, Toronto, May 1998

MOVIE STARS WERE MY MAJOR SUBJECT AT THE ZENITH OF MY CAREER. The thing is, I would never voluntarily call them that. I spent much of the '90s shooting celebrities, as far as I could tell, since "movie stars" were, in my mind, something that existed mostly before I was born, some of them surviving well into my life, but usually far out of my reach as a photographer.

When I had my very strange but memorable portrait session with Mickey Rooney, I actually felt like I was in the presence of a movie star. The rest of the time - as with this shoot with Ally Sheedy, late in my time at NOW magazine - I was shooting celebrities, or famous actors. Movie stars were never close to my age (Sheedy is only two years older than me) and if their fame began at any point in my adult life they were merely "famous."

Ally Sheedy, Toronto, May 1998

Ally Sheedy's fame was white hot over ten years before I met her, with films like The Breakfast Club. She was at the start of a second act in her career when she came to Toronto to do press for High Art, a small film where she played a reclusive lesbian artist. It was the sort of role you took when you wanted to persuade the public that they should stop imagining you as a sullen teenager who shook dandruff onto her notebook during detention.

Ally Sheedy, Toronto, May 1998

That would be a harder job than she might have imagined; when I was printing photos from this shoot for NOW's cover story at the rental darkroom, other photographers - men, mostly my age - would stop and look at the test prints I'd stuck to the white board.

"I loved her in The Breakfast Club," they all told me. "Way more than Molly Ringwald."

Ally Sheedy, Toronto, May 1998

My old standby setup with the back of a hotel curtain draped over a floor lamp to make a gauzy backdrop was getting tired by now. It was was clever and suitable for my Bjork portrait, but by now it felt stale, and this was probably the last time I used it.

I was briefly enamoured with cross-processed slide film again, having finally mastered how to use it without getting blown-out highlights (Fuji 400 ISO film shot as rated) and decided to return to it in search of more vivid colours than I was getting from slide film or (especially) colour negative.

The best shots were taken on one of the big balconies outside the corner suites at the old Four Seasons in Yorkville, in front of a big wall of pebble-finished brutalist concrete. She was very thin, and when she cocked her hip with her hands on her butt I told her to hold that pose; she looked angular and lean and a long way from the sweetly awkward teenager she'd played in her early twenties.

Fashion

Unknown model, Parkdale, 1994

MY CAREER AS A FASHION PHOTOGRAPHER WAS BRIEF AND SPORADIC. Which is to say that I didn't really have a career as a fashion photographer at all, though I have always loved really great fashion work, and had no shortage of ambition to make some of my own.

The reason was simple enough; my favorite photographers shot fashion in addition to portraits and whatever else was their specialty, and some of their most iconic images came from their fashion work. Avedon with Dovima and the elephants. Penn's photos of his wife Lisa in pretty much anything. I wanted to take a lot of great photos, so I wanted to work in as many places that would let me take them.

My first problem, however, was that I was not working in New York City in the mid-50s. It would take me a while to actually grasp that inescapable fact.

My first proper fashion shoot was for NOW magazine, early in my time there. We were doing a special section and the idea was to have the city's fashion luminaries wear the clothes instead of some model. Dierdre Hanna, the paper's fashion editor, made the arrangements and on a day I distinctly remember as cold, wet and miserable Dierdre, the clothes and a hair and makeup artist arrived at my Parkdale loft.

Catherine Franklin, Parkdale, Feb. 1990

Jeanne Beker, Parkdale, Feb. 1990

Ray Civello, Parkdale, Feb. 1990

Jeanne Beker had moved from hosting The New Music - a program I'd watched avidly as a teenager sniffing out the last smokey vapours of punk rock - and had helped start Fashion Television, which became a big deal in the industry. Ray Civello was the owner of some high end salons and had launched his own line of product, and Catherine Franklin was the fashion director for Toronto Life Fashion, one of the two big fashion magazines in the country.

We shot on a day when the thugs hired by our landlord to harass the tenants out of the building went on the offensive, knocking on my door while I was shooting to issue vague threats that I should "get out." Explaining the situation to Dierdre and everyone else in the studio meant that I was more than usually tense while I worked.

I wanted desperately to make a good impression on these people, as they seemed to hold the keys to work I longed to do. I felt like a nervous kid, working at the edge of my technical competence and besieged in his apartment by guys with names like Dwayne and Harry. In hindsight, it's a colourful anecdote. At the time it felt humiliating. Does all of this show in the photos? You be the judge.

Sally, Parkdale, 1991

The results of my first real fashion shoot - which never translated into work with any of these people, by the way - convinced me that as a fashion photographer, I took okay portraits. I needed practice, and the nearest person I could practice on happened to be my very pretty roommate Sally. I'd never lived with a woman who wasn't my mother up till then, so Sally's makeup ritual was something I couldn't help but notice. I was looking at a lot of old fashion magazines, and one day I had an idea.

Left: Erwin Blumenfeld, 1950. Right: Irving Penn, 1959.

I'd finally bought a proper medium format studio camera - a Bronica SQ-A - and after picking up a close-up filter to give the standard 80mm lens some vaguely macro function, I asked her to sit under my little set of strobe lights and set about with her lipstick and mascara. I had come to the conclusion that sharp focus was an arbitrary thing, and likely overrated, so I dialed back the lights and shot with cross-processed slide film rated two stops below the ISO on the box.

I ended up getting something more than vaguely like what I had in mind, which felt like success. (Though it was only while scanning these shots over 25 years later that I decided the bottom shot actually looks better in black and white.) I put one of these shots in my portfolio, hoping someone would respond to what I was trying to do. No one did.

My next kick at fashion shooting came when my old Nerve boss, Dave Macintosh, phoned and said that his new girlfriend was a model whose agent told her she needed more work in her portfolio. He asked if I was interested. Sally had moved out by that point, and I was desperate for a new model, so I eagerly said yes.

Teri Walker, Parkdale, 1992

I rented my favorite sky and clouds backdrop for good luck and explained to Teri my idea for something slightly evocative of surrealism and Magritte. We shot for a while with one simple black dress and then Teri went out to the living room to get the hair and makeup person to give her a new look. I came out and saw the candy-coloured curlers, thought "Eureka!" and said she had to get back into the studio for another setup. I shot negative film cross-processed into slide; it was a trick that didn't often work, but this time it turned out exactly as I'd hoped.

Teri Walker, Parkdale, 1992

We shot for the rest of the afternoon, finally heading outside to get something a bit more "street," which led us to the less salubrious of Parkdale's two diners. I ordered a Labatt's 50, set dressed the table with my own Zippo and Lucky Strikes (Teri didn't actually smoke) and took a couple of rolls. At the end of the day I had a lot of film. I'm not sure if the results were what Teri had in mind, but I'd had a glimpse of what it was like to work with a real model.

It would be two more years before I'd have that experience again. I'd met a young fashion designer at a party somewhere who knew my work from NOW; he asked if I'd be willing to shoot some promo work featuring his clothes. He'd take care of the expenses of models and makeup and I could do what I wanted. It seemed like a good deal, and I knew that I'd never get a chance shooting fashion if I couldn't show off something that featured models and actual clothes.

Unknown model, Parkdale, 1994

We shot with two models and three or four outfits. A set of shots with a model in a bathing suit never did much for me, but the photos I did with the other girl turned out much better. She was young but Eastern European so she looked much older than her age; I recall that she was married, and that she couldn't stop playing with Nato, my very friendly kitten. I honestly wish I remembered her name, because the setup we did at the end of the shoot was probably the closest I ever got to work that looked like the fashion photos I wanted to make.

These shots have Penn all over them, there's no hiding that. But I was able to use props that I liked - a scarred and stained tabletop, an old fan from the attic of my mom's house, and a pair of lemons from my kitchen to set off the model's blue jacket. I shot on slide film, which is unforgiving with exposure, but I was at the top of my game in the studio by then, and everything came out just as I'd imagined. I was eager to work with the designer again, but somewhere along the line he'd gotten some good press and, imagining he could get a better deal, blew me off rather callously. It's why I always remember my favorite fashion shot with some bitterness.

A footnote: The shot just above is not the best one from the shoot. My neighbour across the hall in the Parkdale loft was a set designer/opera singer, and he loved that shot when I showed it to him. He asked if he could borrow it to have it turned into a painting for a show he was doing. It was sent off to an artist to be copied, who then sent it back to his studio, the original slide taped in an envelope to the paper wrapping. An assistant signed for the delivery, quickly unwrapped the painting - and then threw away the paper, with my original slide still attached.

This is why I love digital so much, and why I'll never shoot another roll of slide film again.

Lost slides, ungrateful designers, a generally sour feeling. My attempts to shoot fashion pretty much ended here. I could never find the energy or the resources to throw myself into the cycle of testing and promos and mailers that were required to get a shot at doing paid fashion work. And it would be years before I learned the dirty secret of fashion shooting - that no one really makes money at magazine work, which is just a ritual for gaining favour with the editors who assign the really lucrative jobs in advertising campaigns. Models and stylists and makeup people and photographers work together in a web of mutually exploitative relationships pro bono, hoping that one person's break will buoy a few of them upward. Perhaps I never would have been a decent fashion photographer, but I would have loved to have had a shot.