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Make up artist Derrick Rutledge, whose clients include Oprah and Michelle Obama, is photographed in Toronto on April 16, 2013.Jennifer Roberts/The Globe and Mail

Before becoming Oprah Winfrey's go-to makeup artist, Derrick Rutledge overcame a lifelong struggle with obesity, a story dramatic enough for the Queen of Talk's own show. Aspiring to a career as an opera singer, the native Virginian was told he was too heavy to be a leading man. He found solace and then renown in the shadows of the makeup room, working with the likes of Patti LaBelle, Chaka Khan and a young Beyoncé. Then Michelle Obama came calling. Now, Rutledge has a new natural beauty line, Ü Lifestyle. He spoke with The Globe recently about his career, his famous clients and OW's aversion to chewing gum.

You've been described as a beauty alchemist. Where did that come from?

I guess it's because I worked with chemists to put together an all-natural collection. The approach was to combine healthy products with essential oils for a line that promotes healthy skin and healthy lifestyle.

What kind of products are in the Ü Lifestyle lineup?

It runs the gamut of anyone's beauty needs from hair to makeup and skin care. The colours range from very light to dark, which we'll adjust as we go into different regions. In India, there will be more reds, in Asia more yellows and in Africa darker shades.

How did you start working with Michelle Obama?

A friend asked if she could give out my number for a booking and the next thing I knew I got a call from a weird number. I didn't want to answer it because I thought it was a bill collector! But they kept calling, so I picked up and the woman on the phone said she was calling on behalf of the First Lady, who wanted me to audition to be her makeup artist. I ended up doing her makeup for the St. Patrick's Day dinner at the White House in 2009. For the next 18 months, I was at the White House in the East Wing with the First Lady every day.

When did Oprah call?

Oprah asked her people to find out who did Michelle Obama's makeup and booked me for an audition in New York. I was so nervous that I went into the interview and forgot to spit out my gum. When Oprah's assistant saw me, she stuck her hand out and said, "OW does not like gum." I spat it out. No one is allowed to chew gum in her building in Chicago.

Did you divide your time between Obama and Oprah?

Oprah was well aware that the First Lady came first, but I did work with them both for a while. They both have the busiest schedules I've ever seen. Eventually, I started teaching the First Lady how to do her makeup in case I couldn't be there. I showed her how to contour, fill in her eyebrows and select lip colours that would flatter her. The transition between the two was amicable.

What are some of your makeup tips for dark-skinned women?

The one thing they need to consider is that they can tan or even burn, so a good moisturizer with UV protection is a must. Every woman should have at least two foundations in her beauty bag. I always suggest having one that's a bit darker than your natural tone and one that's a bit lighter to work for all seasons. You can mix the two to find the right shade. If you don't want to wear foundation, get a good concealer to mask under-eye discolouration.

What's the best piece of advice you've received from Oprah?

You get back what you put out. Oprah's a very good teacher and a very giving person, and what I've really noticed over the years is her generosity. I believe that her success is due to her generosity.

This interview has been edited and condensed.