If things had turned out differently, Reba McEntire would have needed to find another stylist. That's because Brett Freedman (VC, ’88) would never have picked up a blow dryer if his first job in advertising had been the dream job he’d hoped for. But fate had other plans, and when Freedman lost interest in the rigid structure of the advertising field, he headed south to Miami in the hopes of turning his hobby of make-up artistry into a full-fledged career – a choice he says was the scariest move he ever made.

“I had always done make up,” explains Freedman. “I had worked at Horne's and Kaufmann's as a make up artist during my Art Institute of Pittsburgh years, and I was always lending a hand to photography students. I wanted to do photo shoots but didn't know how to go about that. It seemed so foreign.”

Freedman landed in South Beach and spent two years creating a buzz at a hot spot make-up shop, obsessing over the faces of teenage models and drag queens en route to his lucky break: a write-up in Allure. From there, word of his stylistic wizardry spread like wildfire and Freedman decided to change his address again – this time to Los Angeles.

“Was it difficult for me to switch gears? No. Was it difficult for my family? Yes. They really wanted me to be stable, have set health insurance, etc. Now that I'm older I completely understand it. My poor Mom What she must have feared, yet [she] held her tongue. She had blind faith. Maybe it was an early twenty-something thing, but I just knew I'd be more than fine.

Since arriving in LA in 1998, Freedman’s star has continued its meteoric rise. He includes Gwyneth Paltrow, Kirsten Dunst, Scarlett Johansson, George Clooney and Reba McEntire among the stable of stars who count on him to help them look their best.

“In the age of HDTV and movies,” explains Freedman, “you see everything now. For concerts, you used to add a bit more 'for the back row,’ but now video walls are so much crisper that it's no longer necessary… Magazines are the best showcases for talent. You can do things a bit more experimental. The actresses aren't in character. They can look as sexy or editorial as they feel...no limits. The camera gets close, the face is still and relaxed. You can really 'see' the make up.”

Freedman credits his father with first opening his eyes to the possibilities of an artistic career that didn’t involve paint or paper.

“My father was a self made man. He was a caterer, which could have meant a very 'by the books' type of business. [But] he is very artistic and creative and he was able to set his company apart. He expressed himself through presentation. I think it was very important for me, as a child, to hear everyone say how talented and creative he was in a field that isn't drawing, painting or sculpting. This planted the seed that, although I was in school for visual communications, I could do anything outside of that and still be considered an 'artist.’”

Now recognized as a celebrity style guru and regularly quoted in top fashion magazines, Freedman has come a long way from his uncertain days in advertising. But hindsight doesn’t erase the trepidation Freedman felt when he first made the plunge.

“I think you really need that confidence and ego from the get-go,” says Freedman. “It's all you have to draw from during the climb.”