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This week marks 21 years on the Toronto International Film Festival circuit for shutterbug-to-the-stars, George Pimentel. The Toronto-based photographer has shot almost every A-lister imaginable along with the swishy so-and-sos of local high society. Here he shares some of the secrets to his success, including why it never hurts to ask (especially when Brad Pitt is involved).

The photographer has two faces

Spending time with my family and friends is my No. 1 priority. My friends are normal, down-to-earth people and they don't even really follow all of the Hollywood world stuff. People don't realize that there are two sides to George Pimentel. Yes, I enjoy the crazy part of my career where I'm in Cannes and the Oscars and back to Toronto for TIFF, but I am just as committed to coaching my son's Little League Baseball team. The summer is a slow season [for the entertainment industry], so I have been doing that for the last few months. We're the Royal York Cardinals. The team banquet was yesterday. It was great, and then as soon as it was done, it's like a switch went off in my brain. All of a sudden I was in TIFF mode. My wife took one look at my face and she knew. This week will be totally crazy. I am shooting 12 parties on Saturday night! If I had one wish it would be that there could be 12 George Pimentels. That way I could go around to every party and make everybody happy.

The lost art of hearing voices

One thing about me that I guess is sort of old fashioned at this point is that I enjoy talking on the phone. I don't like to text, I hate e-mailing. I love to hear people's voices. People know that about me – George is a phone guy. Every day I get in the car and start making phone calls – to clients, to my office. I know that people are so into communicating on e-mail and all of that, but for me there is a value to being the kind of person who picks up his phone when you call. I think it is a more honest form of communication.

Create your own opportunities

The hardest part about my job is that I want to shoot for myself, but it's a business so most of the time I have to shoot what the magazines want – the standard head shots and the full length. Still, I try to create art when there is an opportunity and one thing that I have learned is that getting great photos is always about going outside of the obvious. There was this one time at the Vanity Fair Oscar party a few years ago. I shot the red carpet with everyone else, but then later I went to the valet area where the celebs were waiting for their cars. I saw Scarlett Johansson there and I approached her and asked if I could take a picture. The key was that I kind of caught her off guard. There weren't supposed to be any photographers in that area, but her publicist was down the street trying to organize the car. I got her to look back over her shoulder and I got the shot. I showed it to her and she really loved it. She asked me to send it to her and I did and she remembers me from that. For my own satisfaction I have to take photos that I love and that I'm proud of.

Ask and ye shall receive

When I was new in the game the biggest couple out there was Brad Pitt and Jennifer Aniston. They were coming to the Sundance Film Festival. I had snuck inside the theatre while everyone was outside. As I was scoping it out I saw these two seats that were marked reserved for Jennifer Aniston, Brad Pitt. I decided that I would take the seat right in front of them. I don't consider myself a sneaky paparazzo, but I really wanted to get that shot, so I sat down and waited. I heard the crowd roar as they walked in and got escorted to their seats. When they sat down I just turned around with a big smile on my face and I asked if I could get a quick shot. They said sure. They were in love and happy and young and they allowed me to take it and it turned out to be a really classic photo of a certain period in entertainment history. I will always ask for permission to get a shot. For me, that's part of the job and if they say no I don't shoot it. I hate those deer-in-headlights photos.

A good job is its own reward

I'm a third-generation photographer. My grandfather was the town photographer in a small island of the Azores and both my dad and my uncle were in the same business. When I was a kid I was always shooting church basement weddings and baptisms and helping my dad in the dark room. He gave me one piece of advice: He said, 'If you do a good job, they will call you back.' It's so simple and so true. That is my guiding principle. I get the job done – no excuses. I come home late and I edit in front of the TV. I watch a lot of late-night talk shows and it can be tiring, but the point is that every client knows that the photos will be in their inbox when they open their computers the next day. Everything is done and I can start the next day fresh.