On Friday, October 23, the beauty and entertainment industries lost one of our greats, makeup artist and photographer Jake Bailey. Jake was a huge talent, a friend and a wonderful collaborator, having contributed generously to The Powder Group, On Makeup Magazine and The Makeup Show over the years since we made our first acquaintance. Over the days since his passing, our entire industry, along with his clients including Katy Perry, Selena Gomez and Emmy Rossum have expressed their heartbreak and shock over the terrible loss of such a great man. Jake was a kind, generous, and humble part of our community and we wish his family and friends our deepest condolences. Jake was not one to jump into the spotlight and seldom took center stage, but in the Fall 2013 issue of On Makeup Magazine, Jake agreed to give us a look into his start as a makeup artist, his thoughts on our industry and his own career, why he loved his transition into photography, and so much more. We hope that this look back on his Profile will give each of us some insight on the man and the artist that was, the incredible, Jake Bailey.
– Michael DeVellis, Editor, On Makeup Magazine
Where were you born?
Salt Lake City, UT.
Where do you live now?
New York City
What’s your sign?
Pisces
What did you want to be when you grew up?
When I was a kid I I wanted to be an actor. That was in fact my first exposure to makeup. Participating in local productions and school showcases, we had to do our own makeup. Unfortunately I wasn’t an especially talented actor. By the time I got to high school my dream was to drop out of society and follow the Grateful Dead. Either that, or go into residential real estate.
How did that transpose into makeup artistry?
I always had an affinity for makeup and enjoyed it immensely. I used to beg my mom to let me do her makeup. I wanted her to look like one of the girls from the Robert Palmer videos. Dark smokey eyes and red lips. I also strongly suggested she embrace more glamourous evening attire. Preferably something with sequins. However growing up in Salt Lake City, it never occurred to me that makeup was a viable career. It wasn’t until I moved to NYC that I realized the possibilities.
What was your first memorable work as an artist?
I would have to say it was the small scale palace I built out of empty toilet and paper towel rolls and tinfoil when I was in the first grade. Either that, or the Marilyn Monroe themed Valentine’s day box I made in the second grade. It was designed so that you could deposit the Valentine envelopes into her cleavage.
How did you know that the makeup artist industry was the place you wanted to build a career?
When I first moved to NYC when I was 18, I made my living modeling for catalogs and TV commercials. A photographer I had worked with found out that I had some basic makeup skills and offered me the opportunity to do makeup on the graduating class of the American Academy of Dramatic Arts as he was shooting their headsets over three days. He had no budget for makeup but suggested that each graduate tip me $20 dollars and I made $600 dollars. It was the best time I had ever had at work. The days flew by and I met a lot of interesting people including a couple of actors who would meet success and become my clients a few years later. I remember crossing the street at 6th Ave an 14th St while on the phone with my mom and telling her about the job. I told her I had never enjoyed a day of work so much in my life and that I knew this was what I wanted to do with my life.
What do you love about working in makeup?
More than anything, I love getting to collaborate with so many creative people. The actors, photographers, Stylists and hair stylists that are a constant source of inspiration.
What makes your work interesting to you?
I love that no day is ever the same. Each day presents a new experience. Different location, interesting people, and creative challenges.
What challenges do you face working as a freelance artist?
Of course the greatest challenge of being a freelancer is the financial insecurity as you never know where your next job is coming from. I have a steady clientele now, but in the beginning it was a great challenge never knowing where your next paycheck is coming from and how much it will be. Chasing those checks down is no picnic either. These days, I live off last year’s income and try to live well within my means just in case I hit the skids. Every-time I have a slow period I’m convinced my career is over. This dynamic works for me however, because it keeps me on my toes. Knowing that each job could be my last propels me to bring 100%, and more, to every job that I take.
Do you have a signature style?
I hope not. I try not to get stuck in any particular style. I thinks it’s important as an artist not to let the grass grow under your feet. I’m always trying to get better, learn from my mistakes and evolve. It’s also very easy to get pigeonholed in a particular niche if you get too well known for doing just one thing. It’s important to maintain your versatility in order to stay engaged and inspired on a daily basis.
What’s coming next in makeup?
In the era of Photoshop and HD cameras I see that standards for the quality of makeup are rising. It used to be that on camera there was a loss of information that was quite flattering to the makeup and the person wearing it. These days, you see every pore, so the makeup had better be flawless. With Photoshop we are constantly exposed to unrealistically perfect images, and it has raised our standards of beauty. Cosmetic companies are scrambling to improve the textures and quality of their product while makeup artists like myself are constantly searching for better techniques to achieve something as close to perfection as possible. While I’m thrilled about the better quality of cosmetics I have access to, I feel it’s important that women remember that these images in the media are illustrations of beauty rather than truthful depictions.
What should someone who is looking to develop a career in makeup know before getting into the business?
It’s a tough road these days. It’s more competitive than ever so it’s important that you are passionate about it. In the beginning, you have to take every opportunity that comes your way, whether it pays or not, because there is always something to be learned. Also, realize that there will be many screw ups and setbacks. The path to success is paved with failure. It’s better to screw up and have your learning experiences on a test shoot than on your first cover or celebrity client.
What are some of the most important qualities that a makeup artist can have?
I’d say patience and sensitivity. You are working with people’s deepest insecurities in an unusually intimate environment. Sometimes the people I’m working with are extremely nervous and/or stressed, so I try to be forgiving and gauge just what they need from me and how I can make them feel comfortable and beautiful at the same time.
What makes you a good makeup artist?
Attention to detail and not being afraid to admit I’ve made a mistake and correct it. The ability to compromise and be open to other people’s ideas. That, and the patience and sensitivity mentioned in the previous question.
Is there a project in your career that you are most proud of?
My proudest moment as a makeup artist was when I was working at the M.A.C. counter at Macy’s Herald Square and a girl whose makeup I had done started crying when she looked in the mirror. She told me she felt pretty for the first time in her life. She was a beautiful girl with great features — she just needed a little polish to bring things together and accentuate her beauty. I was grateful that I had used waterproof mascara.
What inspires you?
Art more than anything else. I’m lucky enough to live in NYC so I have constant access to some of the greatest museums and galleries in the world. If ever I feel stagnant, I’ll visit the Chelsea galleries or the Met and I leave bursting with creative energy.
Whose work do you admire?
Of course my mentor Kevyn Aucoin, as well as Pat McGrath, Mark Carrasquillo, Charlotte Tilbury, James Kaliardos — I was lucky enough to be able to assist all of them. Also Tyen, Topolino, Serge Lutens, and the illustrator, Antonio Lopez.
How do you continue to grow your career as an artist?
I just keep showing up with a smile — usually on time.
What project did you have the most fun working on?
Last year I spent fashion week in Paris with Katy Perry doing her makeup and photographing her in every look she wore that week. It was an enormous amount of work playing both makeup artist and photographer for eight days straight. We also took advantage of everything that Paris nightlife has to offer so suffice it to say I slept very little. However, Katy and I produced a treasure trove of beautiful images that have already been published on several magazine covers including her latest Billboard cover.
When did you first become interested in photography?
I first started taking pictures for my high school yearbook and I’ve been taking pictures ever since. I always enjoyed taking informal portraits and urban landscapes. When I first got into makeup in NYC, I thought about trying photography as well, but it’s extremely expensive to pursue and I didn’t have the money for the education or the equipment needed for studio work.
Why was it of interest to you?
I see beauty everywhere and in everyone. Photography gives me the ability to record that beauty and share it; find those moments and keep them forever. While someone can be really breathtaking in person, it can be difficult to capture that essence on camera. There’s nothing more satisfying than capturing the moment when everything comes together and that person’s beauty is fully expressed.
What makes photography a good creative outlet for you?
Its certainly an additional challenge for me and I think every artist should strive to remain challenged. It’s also incredibly satisfying to have some creative control over the final results of your efforts. Often times as a makeup artist I may be very proud of my work. However if it is lit badly or poorly retouched it can be disappointing to see the final result and feel that your vision was not expressed. I think every artist enjoys seeing his or her work presented exactly as it was intended.
Do you have a shot of yours that is your favorite thus far in your photo work?
It’s so hard to say as I’m too close to my own work to really evaluate it and choose a favorite. There are a few pictures of Katy Perry that are undoubtedly everyone else’s favorite as they keep getting published. However my favorite picture I’ve ever taken is one of my oldest nephew, Nico, on a train in Madrid. My most beautiful pictures are always of those who I love the most.
What are the elements of a good photograph to you?
Composition is extremely important, but first and foremost it’s always the moment. In a successful shoot the choice should always be obvious. That one shot that stands out from the rest. If there isn’t that one shot, I often think of the shoot as a failure. There should always be that magic moment that leaves you no other choice.
What is your focus moving forward, makeup or photography?
Ideally it would be both. I have such a passion for makeup it would be difficult to leave that behind entirely. There are a handful of makeup artists who have been able to combine the two; most importantly Tyen and Serge Lutens. That would be my ideal. However, photography can be an all encompassing career. Should I go down that path, I would certainly have to still do the makeup on a portion of my shoots. God bless the makeup artist that has to deal with working for me! Right now, I am currently working on a fine art project involving abstract makeup, mixed media and photography. I really do love it all.
Makeup and Photos Jake Bailey