In 2005, Jaime Pressly was the girl from Not Another Teen Movie who had just landed a sitcom. Two years later, she won an Emmy.
I photographed her on a downtown Los Angeles rooftop between those two facts. This is the story of that shoot, and of the five pictures on a flip phone that started my career.
The meeting
I moved back to Los Angeles in 2005 and met Jaime Pressly at a party. At the time, she was a sex symbol, known for Not Another Teen Movie, and she had just been cast on the show My Name Is Earl. I was a 22-year-old kid, fresh out of college.
I started talking to her and told her I was a photographer. She asked what type of pictures I did. I told her fashion, and that I had just shot the campaign for San Francisco International Fashion Week. Then I did something that would be unthinkable today: I showed her my flip phone, which had a one-inch screen, and walked her through five pictures of my work.
She told me she liked my work, and asked if I could do a shoot for her clothing line. Of course I said yes.
The rooftop
We shot at her building in downtown Los Angeles. Her clothing line was filled with dresses, tops, and leggings, primarily made of jersey material. I shot her and two models on her rooftop.
Jaime set up the set herself: a bohemian Moroccan arrangement with a lamp and an Arabic rug. We shot with the skyline of downtown Los Angeles behind them and used the natural light of the sunset to get a nice, soft glow. Jaime wore sunglasses, knee-high boots, a skirt, and her hair in messy curls. She had one of the best six-packs I had ever seen.
She loved the pictures, and she ended up using me for her next two campaigns.
The night that followed
After we wrapped the shoot, she took us to Geisha House in Hollywood, which was one of the hottest restaurants at the time. I was so excited to order Kobe beef and rock shrimp. Geisha House was one of the first restaurants to carry Kobe beef in Los Angeles.
Over dinner she told me she had a house in Newport Beach and that she had been going to a club called Sutra, which was known for having the best DJs come through. It was definitely the hottest club in Orange County, and she told me I should come check it out with her. I was very excited.
The pictures were published all over: US Weekly, InStyle, Vogue, and even Perez Hilton, which was the leading blog at the time. That shoot was pivotal for getting my name out there and building my credibility as a celebrity photographer.
Before she was famous
Here is the timeline that matters. When I shot her in 2005, My Name Is Earl had not premiered yet. She was the rising girl with a sitcom on the way, not the Emmy winner. Two years later, her performance as Joy Turner made her an Emmy winner and a household name.
Jaime's quote opens this chapter of my memoir: "If you want to do something, just do it. No one is going to do it for you." She lived it. That night at the party, walking a stranger through five pictures on a one-inch screen, so did I.
The takeaway for photographers
Everyone remembers the sunset light on that rooftop. What I remember is the portfolio that won the job: five pictures on a phone screen.
When you are 22 and unknown, you do not need a website, a reel, or a deck. You need five images that are undeniable, and you need to be in the room. Jaime did not hire my production value. She hired what she saw in those five frames.
I still run my business on that principle. A fashion photographer in Los Angeles wins jobs with the strength of the work, not the size of the package around it. And when you are hiring a celebrity photographer, ask to see the five strongest frames, not the follower count. That is what Jaime did, and she picked a kid who would still be doing this 27 years later.
Frequently asked questions
When did David Christopher Lee photograph Jaime Pressly? In 2005, for her clothing line, on the rooftop of her building in downtown Los Angeles. He was 22 and fresh out of college.
Was Jaime Pressly famous when he photographed her? She was on the rise. She was known for Not Another Teen Movie and had just been cast on My Name Is Earl, which had not premiered yet. Her Emmy win came two years later, in 2007.
Where were the photos published? US Weekly, InStyle, Vogue, and Perez Hilton. The shoot was pivotal in building his credibility as a celebrity photographer, and she hired him for her next two campaigns.
How do I book a shoot? Get in touch here. I have spent 27 years as a celebrity photographer in Los Angeles and New York, and every session gets the same standard.
About the author: David Christopher Lee is a Los Angeles celebrity photographer with 27 years of experience, shooting for GQ, Vogue, InStyle, People, and brands around the world.
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