Art Success. Adelaide Damoah in Conversation with Tim Okamura

Tim Okamura is a Canadian artist most well known for his beautiful and realistic depictions of African Americans and other minorities in urban landscapes. His stunning and positive depictions of groups of people who have rarely been treated with such dignity in art history are a powerful testament to his views on racial differences and the problems that focusing on these differences can bring to society. Born in 1968, Okamura obtained a Bachelor of Fine Art degree from the Alberta College of Art and Design in Calgary, Canada. He subsequently moved to New York and obtained his Masters in Fine Art from the eponymous School of Visual Arts. His career highlights to date include his paintings being featured in several motion pictures, being selected for the prestigious BP Portrait award for the National Portrait Gallery in London five times and being short-listed to paint Queen Elisabeth in 2006. Tim took some time out from painting and marketing his latest Kickstarter project, “Heavyweight Paint,” to discuss his views on success in art with me.

Tim Okamura

Adelaide Damoah (AD: I read that your work is influenced by urban life and hip hop, which is interesting to me because of my love of music. 

Tim: Yea, I used to have a hip hop radio show when I was still in Canada in the late eighties and early nineties. I actually had the only hip hop radio show in the city so it was a great opportunity because when some of those early artists went on tour, they came onto my show. Most notably, Will Smith and Ice T were on my show. A few people who were just at the top of their game at that point in time came on the show. It was very cool.

Adelaide Damoah (AD): I see that you have had several solo shows since graduating. What year was your first solo show?

TO: It actually took a while because I was doing a lot of stuff for advertising agencies. I was doing story boards and commercial art, illustrations for album covers and that type of thing… I think I had the first show of my work in around 1999 or 2000. It probably took about seven years from graduation for me to do a solo show.

AD: So after graduation you were doing commercial art as opposed to fine art.

TO: Yes. It is so hard to make that transition from graduating art school to really making a living with your work. I sort of had a plan to work commercially and do things in advertising where I was at least still drawing and painting while at the same time still trying to improve my technical skills. By the time I started doing my own work, that was still a work in progress and very much a learning curve. In a lot of ways, I was far from ready, even after getting my masters degree. The sheer volume of work that I did commercially helped me to build up a better toolbox of skills without being under the spotlight of a gallery.  I was able to make a lot of mistakes. The work was seen of course, but I never felt that personal attachment to it that I do now when I show my work in a gallery. It was a long gestation period before I was able to start showing MY work. Everything for a reason but I was certainly glad that I was able to take the time to try to hone my skills and get better at my craft.

AD: Did you sell anything at your first show?


I think I sold one or two! I set the bar pretty low when I first started. I did not have any expectations. My early shows were breaking even and that was a victory to me.

Tim Okamura in the studio

AD: At what point were you able to go full time doing your work for shows?


I would say probably around the time I started to do art work for films. I worked on a film in 2004 called Prime staring Uma Thurman and Meryl Streep. They featured a lot of my work and I also did a portrait of Uma Thurman which did not make the final cut of the movie. Right at that time, I was able to make a little bit of money from the film and I also happened to have a couple of sales in London and elsewhere which helped me to make that jump. My friends helped as well. I specifically remember saying to my friends,

“If I am still working in the commercial industry in another year, please kill me!” 

I just couldn’t take it any more, so all of that came together at the right time before I had to take drastic measures!

AD: How did you get into film?

TO: A number of different ways. It was an interesting series of circumstances. I had a commercial agent whose brother was a location scout. The very first thing that I did was a portrait, a projection of what Richard Gere’s father would look like in a movie called “Unfaithful.” That was one way I got in. Another way was I had some paintings hanging up in a club in Brooklyn. I ended up having the paintings incorporated in a film called School of Rock with Jack Black. They saw the paintings and liked the aesthetic that they added to the club so they wanted them in the film. Then a guy who became a good friend of mine, a writer director named Ben Younger, he had done a film previously called Boiler room with Ben Affleck and Vin Diesel…

AD: I’ve seen Boiler Room…

TO: Yea, so he was coming off of the success of that and starting on a new project which came to be Prime. He moved into Williamsburg. He was living in a loft just down the street from my friends club with all these paintings hanging. He got in touch with me and he was going to make the main character a writer. After seeing the work and talking to me, he decided to make him a painter. He called me up and asked,


“Would that be OK with you? Can we use your paintings?” 

I said, “Erm, let me consult with my management team… Yes, yes, that would be fine!” 

Haha! That was actually a while before we did the film. I mean, that must have been around  2001 or 2002… The chips were down because we were still in the wake of 911 here, the economy was crap and everybody was struggling. That was a really encouraging thing that happened with that film. After Prime, I ended up doing paintings for and having some existing paintings shown in an Ethan Hawke movie. He did a screen adaptation of his novel called, “The Hottest State.” There were a few others… I guess I got my foot in the door and then my name got passed around a little bit. I was meant to work on a Spike Lee film recently but that got put on hold… I hope it comes back around because I enjoy working with film people. I usually work in solitude and it is kind of fun for me to go into that world…

AD: I have seen that a lot of your subject matter seems to revolve around hip hop, placing ethnic minorities in urban settings… How did that come about? Why is it that you were particularly influenced by those things?

TO: I think it was a confluence of different influences and interests. I was interested in Hip-hop in a big way. In a way, it was sort of my Punk Rock I guess. Growing up in Canada, it was so different and for me to be into Hip-Hop was completely growing against the grain in terms of what everybody else was into. That was a part of it. Every aspect of it I really enjoyed. Break-dancing… I was never good but I aspired to be good! So many individual aspects like graffiti were huge for me. When I moved to New York in 1991, I was very much in that mind set. I had moved to this city which was to a large extent the birth place of Hip-hop and graffiti. The fact that I had always been interested in portraits sort of lead me to marry the two ideas. I decided to paint some of the people that had created this…

The Royal Guard. Copyright Tim Okamura

When I first got to New York, I was spending a lot of time painting a lot of rappers and DJ’s- without actually getting them to sit for me. It evolved over time and I think that some social awareness and social consciousness became an important aspect of what I was doing. I realised that in painting, a lot of African American women and certainly ethnic minorities, had not been represented very much in the history of painting and certainly not in a classical academic style.  I found that there were interesting stories that could be told through the portraits… I had painted men primarily for a long time and I think there is a little bit more leeway with men. You can get a little more expressive, or a little more rough sometimes with the depiction and they still work. But with women, there is a level of sensitivity that is required to sometimes capture what can be very subtle beauty. That is was part of the challenge too. Can I even do this? Can I do justice to these subjects…

Courage. Copyright Tim Okamura

I am half Japanese and my mothers heritage is British so I am this half white half Asian guy painting black women and that question does come up a lot. It is certainly a very valid question and I think that it is not necessarily a short answer for me. There are different aspects to my motivation… Number one, I feel that there are interesting stories to be told and I am not going to sit and wait for somebody else to tell them. I want to tell those stories. I feel that my intentions are to portray these women with a real strong sense of respect and a strong sense of wanting to show their subtleness, strength and their beauty. I am not going to stop myself based on the fact that I am not a black woman!

It is interesting with figurative art because that is how people make connections. The want to show this line between these two poles. It’s like, you are a white man, therefore you should be painting white men or white people. You are an Asian man, therefore you should be painting Asian men or people… It is almost like being at school or something, with people saying,

“You are going to paint these people because you know them.” 

Listen, I think, what better thing than to explore people that you don’t know that well? I think that that is a huge motivation. I think that most artists explore subjects that intrigue them and that they want to learn more about. It takes a longer answer to explain… I don’t necessarily think it should but I understand it and I certainly feel comfortable talking about it. The response has been overwhelmingly positive…

AD: It is very interesting to me. I understand exactly where you are coming from because somebody who is not black, who is painting black people is a rarity. You and another artist who I interviewed earlier this week are the only two non black artists I have interviewed so far who feel somehow compelled to paint black people. I find that interesting and I think it is a good thing because I think that people like to focus on our differences rather than our similarities, too much. Once we start focusing on our similarities rather than our differences, a lot of problems will be resolved. 

TO: That is exactly it. I could not have said that better myself. I hope that what people take away from the work is that you may approach it with an initial reaction that the subject is really different from yourself, but then you spend time with the piece… Eyes are very important to me in paintings. You look in that persons eyes and you get a little bit of an energy… Then you walk away thinking about all of the similarities you have with that person. How you are sharing similar emotion that obviously transcends any of the surface differences.

Obviously people are always going to be critical. I think that when people are looking at it through a negative filter, their gut reaction might be that it is exploitative in some way. Honestly, nothing could be further from the truth. In fact, I think that it is more of a risk for me… Not that I look at it that way, but gosh, if I was going to choose to paint anybody and be concerned about making money let’s say, the least obvious choice would be the subjects that I have painted. But it was always a natural progression for me and in that way, I am very happy to talk about that and to answer that question because I know where my heart is at. Things can get very convoluted with art, in the art world and  for me I know that the connection is really strong, really pure and it feels good to know that. Like I said, I can talk about it for a long time! It is not gimmicky, it comes from a natural interest in other humans and wanting to depict human beings who have not had their fair share of documentation and respectful depiction.

One more thing, when you were talking about the fact that you only knew of one other artist that was painting black subjects, I think that one other thing I wanted to add to that is that I have been very fortunate in that I have had quite a bit of exposure in recent years, so my name probably comes up when it comes to that. But, honestly, there are so many artists that write me emails and letters and there are some female painters who do nothing but paint black women. And they are comfortable with that. There are a lot of people, especially in the younger generation who are very excited about doing this cross cultural type of work who I just think have not gotten the same amount of exposure that I have. I am more than happy to break some new ground and answer questions from them

AD: Considering everything you have achieved to date, what would you say success in the art world means to you?

TO: It is a bit of a tricky one for me because, being in New York and being in the scene so to speak… I think most of us artists have pretty big healthy egos and I think that most of us are extremely ambitious. I do know people who are happy to just make money from their work without being famous and that is their definition of success and I feel that. I do. But, I am ambitious and as I continue to move forward and I feel like I am about to tap more challenging themes and I feel like the work is slowly but surely getting better, I would hope that it would… I feel like, yes, I would like to get more exposure. I would like to see how far I can go. I don’t think there is anything wrong with that. I just think that it is sometimes a slippery slope, because you get caught up in comparing yourself to others. The further you go, the more people you see and the more ladder there seems to be up ahead of you… Sometimes, it can be a little daunting and you have got to have a strong base of confidence and a strong philosophy about life. Not comparing yourself to other people, we are all on different paths… It is hard. It is confusing in the New York art scene. There are many days when I sit and meditate and sort myself out a bit…

The Ascension. Copyright Tim Okamura

But to answer your question more directly, I think that having a gallery that supports you and understands your work, that is certainly a huge pillar of success. Being able to make a living off the work is another important aspect. I think the most important of all is really feeling like you are connecting with people. I have been very fortunate in that respect, in that I do have people take the time to email me and tell me,

“I’m feeling your shit man!”

Whether it is people in school, in high school.. It kind of blows my mind, when I get some 17 year old kid from Surrey in England, taking the time to email me to say that they are really affected by the work. That is awesome and is a huge part of me feeling a success…


AD: By your definition, would you consider yourself to be successful? 

TO: Yes, to some degree. It is a little tough. When you are in your own shoes, it is harder to see where you are at sometimes. I think from other peoples perspective, from their stand point, it is like a slam dunk. But like I said before, the further you climb up the ladder, the more you see ahead of you. I never really sit and pat myself on the back or anything like that… Well once in a while, I have to take a moment to be happy that I have survived, that I have made it this far or whatever but I guess I am always looking ahead, so it is kind of hard to be thinking that way.

AD: It is good to pat yourself on the back once in a while!

TO: Yea! Well, just as long as it does not make you complacent. I am always trying to think two steps ahead because I am always trying to do better work.

AD: Thinking about all of your achievements to date, what do you feel is your biggest success and why?

TO: The people I have connected with have been people I never would have expected to connect with. That is one huge thing. I usually do get more emails from France, Italy and Australia. It’s great! I probably never really would have imagined that when I was younger so that is a sign of having some success for sure…  There have been some fun moments. Working on the film stuff has been fantastic. Going to the premier of Prime… They gave me my own limousine! It was just fun to be a part of the whole Hollywood thing for a while. Conversely, the short-listing thing, well it was not really super formal, but it was the Royal Surveyor of the Queens pictures who had seen my work at the National Portrait Gallery in London, who invited me to come and speak with him at St James Palace! I had to check in with the  Royal Guard there and I sat in this grand tea room in St James Palace speaking with him. That was a very unexpected moment. It certainly made me feel at that point that I had at least done something worthy of conversation.

The Coronation. Copyright Tim Okamura

AD: How far did that go? 

TO: It sort of ended there. It was actually a learning process for me because I didn’t realise that it is not the Royal Family commissioning portraits. It is all these different societies that they are the figure head of. He said they may contact me, but in leaving he said I would probably be more suited to painting Prince William or Prince Harry than the Queen. This is going back a few years, maybe 2006 or something like that. I never did hear back from them. I think maybe their preference would be to use an English painter for something like that. It was cool of them to be thinking outside of the box. Obviously, some of my work gets pretty edgy but maybe he saw something in there which he thought may have been a cool, unexpected direction to go in. I couldn’t have done any graffiti on the background of the Queens portrait!

AD: No! Imagine that!

TO: Yes! It would have been a fun project.

AD: What would you say was your biggest failure or set back?

TO: As far as specific events, there have been several shows where I have been banking on making money to live from and I put everything I had into the show in terms of costs and the show was a dud. That has happened several times. It is kind of a gamble and I still consider myself to be an emerging artist in a lot of ways. It is never a slam dunk when I do a show. There are certain galleries where I do very well and at others it is more of a crap shoot. That is tough… I don’t think those were necessarily mistakes that I made, but more the galleries were the wrong ones to show at. It has sometimes been a bit of a gamble.

I was in bands for a number of years Singing and touring. That was something that I loved doing. I love singing and performing, but I think it delayed my progression as a painter. I would never give that up though. I don’t think it was a mistake. Sometimes I wish I was where I am at now five or 10 years ago. But I think everyone does that. We all take a certain path and make certain choices… It is happening now… Maybe I was not mature enough anyway to handle the demands of it all. Who knows!

AD: When I have had shows and not sold anything, I have felt really down about it. How did you overcome that and continue?

TO: It is hard because of the financial repercussions. I have sat down and thought, oh my God, I am really screwed here. There have been times when I sat there and thought I was too ambitious with the work, and maybe I should have done smaller pieces… I think you just have to check those thoughts… For myself, one thing is I always know I try like hell to do the best show that I can, so I know that it is not because of being lazy or lack of effort. But after a show, there is that kind of vacuum if it does not do well where you just sit and think. But at a certain point, you know that there is no plan B anyhow so you just have to figure out how to survive in the wake of a disappointing show and just start working on the next one. You can not just sit there and wallow in it because you are just going to make it worse! You might as well do everything you can to start working again, as soon as you can. A lot of the time, I have sold a painting down the line that someone was not sure about at the time of the show. Or I have taken the work to a different gallery, or pieced it together somehow and kept moving forward.

Progressive Youth. Copyright Tim Okamura

AD: When that has happened, have you done other things to bring money in?

TO: When the chips have really been down, my family has helped me. There have been times when my parents have had to keep me going! My sister, my brother… You know, thank God, I mean without the family support that I have had, I would have been done for a long time ago. There have been many times when they have really bailed me out when my back has been against the wall. Friends have sometimes helped too. I think as an artist, your friend network is super important. They become like another form of family. When other guys are down on their luck and you are up, maybe you lend them money and when you are down and out they lend you money! That is kind of how you keep going. Unfortunately, it is not a career where you have a smooth upward calculated trajectory. You need the support network, but, not everybody has that. I can see how people end up having to go in another direction because they just can’t do it any more. Luckily, I have been able to avoid that.

AD: What advice would you give to an up and coming artist wishing to follow in your direction?

TO: I am resisting the urge to give the cheeky answer!

AD: Give the cheeky answer!

TO: The cheeky answer is quit immediately, do something else! No, I would never say that. I think you do need to have a little bit of a realistic plan. Luckily, I had some friends who were able to point me in the right direction in terms of having a short term, medium term and long term plan. My long term plan was always to be a painter. The medium term was at the point when I was interested in doing commercial art with album covers and books. That was a medium term thing, doing the commercial art, freelancing, hustling, having an agent…

When I first got out of school, I got a job at an agency just doing graphic design. I worked as a waiter, a bar tender, a bouncer… Just anything I could do. I think you are just in pure survival mode when you get out of school. Planning the stages is a huge part of it. You need to realise that you have to always be working on upgrading and mastering your skills and working non stop with the awareness that it takes time. I think sometimes it is a huge mistake of certain dealers who want to exploit someone who is doing something kind of hot for a minute. You then get these 24 and 25 year old guys getting out of school and being celebrated when they are not yet fully formed. It is very rare that you get young art stars who are 24 or 25 and that is something that I think a lot of art students don’t necessarily realise. It is like making it in the music industry. Do you know how many thousands of singers there are trying to make it in the UK and in America, wanting to be on Top of the Pops or whatever… The reality is that it takes a long time, it takes complete and total dedication. An actor friend of mine, Brian Greenberg said to me,

“The only reason why I am an actor is because I never had a plan B.” 

It is the same for me as a painter, there is no plan B, so you do what you have to do to keep going. I had an instructor in grad school who said to me,

“Listen, I will tell you the same thing my instructor told me when I was in school. For anybody that sticks it out, you have to give yourself at least 10 years before your technical skills, your ideas and your opportunities mesh. After that, you actually start to do some shit!” 

I always have that in the back of my head. He said, “I am not lying to you, I am not trying to scare you, it is reality.”

It was almost ten years to the day when I did my first big show and I realised that he was so right.

AD: Do you have any new shows coming up?




TO: Yes. There are two things that are coming up for me. One is my gallery in New York which it is going to the Toronto International Art Fair. It will just be myself and another Canadian artist named Martin Whittfooth who will be showing together in Toronto. That should be fun! I have not done the Toronto International Art Fair for a few years and I’m excited.

Headdress. Copyright Tim Okamura

The next thing after that is a big four man show which I am doing with three other friends who are also figurative painters here in New York. It is in a fabulous gigantic space called the Art Directors Club in Chelsea and we are doing it as a n independent exhibition with a charity partner and a youth organisation. Our theme is boxing so that is going to be exciting… We are all doing different takes on the boxing theme. I am doing female boxers. I have been buying all this vintage antique boxing gear like boxing gloves from the 1890’s, boxing shoes from the 1920’s… I will have my models wearing this antique boxing gear… It is actually the climax of a documentary that we have been filming, that we have been the subjects of. We started filming last March. The basic story is about the four of us trying to put on this show against all odds. It branches off and explores our individual lives and artistic practices. It is me showing for the first time with three very good friends of mine who are fabulous artists. The exhibition is also the climax of the film.

I had a show here in New York in September and I really hadn’t shown in New York in many years and even in a gallery for a big chunk of time. That show got lots of attention and I feel like this is kind of like a follow up that even more people will be able to check out. It is an important show for all of us.

AD: When is that going to be?




TO: It opens on December 10th at the Art Directors Club in New York City. We don’t even have our title yet! We have our theme, but the title of the documentary is Heavyweight Paint. We actually have a Kickstarter campaign going right now. There is a trailer for the film which gives a little bit of a taste of what the film is going to be like.

Tim Okamura in his studio.

Tim Okamura website
Tim Okamura is currently represented by Lyons Wier gallery in New York.
Follow Tim Okamura on Twitter…
Like Tim Okamura on Facebook…
Heavyweight Paint Kickstarter Project.
Official Heavyweight Paint website

An abridged version of this interview will be published in the September edition of Lime magazine with thanks to editor Vernia Mengot.