What It Was Like to Draw Britney, Lindsay, and Paris During Their Day in Court

This Week in 2007 is a weekly column looking back on Lindsay Lohan, the first iPhone, George W. Bush, and everything else we loved about the year 2007.

"You could hear [Hilton] calling for her mother," Edwards recalls. "It was really sad. Lindsay Lohan didn't expect to be handcuffed in a Beverly Hills courthouse either."

Edwards is one of the few people who has attended both Hilton's and Lohan's court dates. As a Los Angeles-based courtroom sketch artist, she has drawn famous defendants since the late 70s. She's captured everyone from OJ Simpson to Michael Jackson to Winona Ryder. ("[Her case] was all about what she was wearing to court, not shoplifting!" Edwards says.) Her drawings were even collected as an art book called Captured! Inside the World of Celebrity Trials. For years, her subjects consisted of murderers who became famous through their trials (see: the Menendez brothers, who shot and killed their entertainment executive parents) and movie stars.

In 2007, the attention of Edwards's beloved Los Angeles shifted from Academy Award nominated defendants to reality star socialites accused of drinking and driving. "2007 was really interesting," she remarks. It was the year she drew the decade's most memorable women, from Hilton to Lohan to Nicole Richie to Britney Spears.

During the 1960s, Edwards grew up a world away from the Lohans of Long Island. She lived in the ritzy neighborhood of Coldwater Canyon outside Bel Air with her brother, Martin Shafer, would go on to found Castle Rock Entertainment, the production company that co-produced everything from When Harry Met Sally… to The Shawshank Redemption. Their mother worked as a painter and jewelry designer. "My family always had a lot of celebrity friends," Edwards admits. "I mean serious celebrity friends. I don't mean TV people. I mean film people."

Whenever a young Edwards grew bored, her mom told her to draw. Her earliest subjects were princesses. She submitted drawings to competitions, and after high school graduation, she studied fashion illustration at the Art Center College of Design in Pasadena, California. Edwards finished college at age 19, and then began searching for work as a fashion illustrator in Los Angeles. She drew brochures, drafted for designers, and sketched models as they walked down the runway. The process taught her how to work fast and capture movement. She assumed she'd draw fashion stills for life.

"Courtrooms were kind of a happy accident," she says. One night, she was watching local news with her husband and spotted terrible courtroom sketches. "I could do a thousand times better!" she recalls telling her husband. She called a local news network and scheduled a meeting. They looked at her portfolio, a collection that Edwards describes as "all beautiful people in gorgeous clothes. No murderers!" The network executive told her, "You should stick to fashion."

"That just angered me!" Edwards says.

She called a second network and convinced them to give her one opportunity: sketching the Michelle Triola Marvin case, which established palimony laws for unmarried couples in California. "I had absolutely no clue what to do, so I fumbled through it," Edwards recalls. "I watched a couple of other artists that were there. Right away it just clicked. I was in love with the spontaneity of it."

She spotted how her fashion training could push her to excel in the courtroom. "I think [fashion illustration and courtroom sketching are] quite similar," she says. "As a fashion artist, speed is very important… [In court], you can't say, 'Bailiff, can you bring him back? I didn't finish his eyebrows.'" Where a portrait could take days, both courtroom sketches and fashion illustrations need to be completed often in five to 20 minutes.

For the early part of her courtroom sketching years, Edwards witnessed the trials of celebrities like Michael Jackson, who fell from popularity thanks to a child molestation lawsuit and subsequent trial, and criminals like Heidi Fleiss who set up powerful actors' and politicians' rendezvous with sex workers. Witnessing the trials changed Edwards's view of her hometown.

"Growing up, that was Beverly Hills. I went to school with a lot of celebrities' kids. It was a very nice, quiet, cute lifestyle. There were a lot of deer up in the canyon at the time. It didn't prepare me for anything. I saw one side of life," she reflects. "Doing courtroom work, I see another side of life. It's kind of strange because fashion was all about beauty and expensive clothes, and then I went to crime and the sadness and loss and victims and punishment."

Throughout the mid-2000s, fashion served as a focal point in her court drawings because of the new types of celebrities hounding Los Angeles's clubs and courthouses. One time, Edwards recalls, Kim Kardashian walked through the front of the courthouse although security would have allowed her to take the back entrance. "Kim Kardashian comes to court demanding to go through the front of the courthouse," Edwards remarks. "She wanted to be photographed. She came wearing a cocktail dress to court. Very strange!"

One of Edwards's most famous sketches stemmed from Lohan's daring courthouse fashion choice at a September 2010 hearing. Judge Elden Fox summoned her to court after she failed a drug test, and she arrived in a white skirt and blazer. He revoked her probation, and cops handcuffed Lohan and whisked her out of court. As paparazzi shot their cameras, Edwards spotted their flashes reflecting off Lohan's Christian Louboutin heels.

"The flash of the red sole of the shoes were my kind of my a-ha moment of the day," she remembers.

Her illustration was syndicated by newspapers across the world, and the Louboutin office even emailed her a thank you note. "It turned out to be all about the fashion, not about the crime," Edwards explains.

Stars have always held vapid views on their appearances, but before Ryder's shoplifting case, actresses would never have worn Louboutins to court. "[Los Angeles is] the center of crazy," Edwards says. "I couldn't do what I'm doing anywhere else. In New York everyone takes themselves waaaaaay too seriously." But if a celebrity appeared humble, Edwards believes the artist should reflect that and always treat celebrities like any other defendant or witness. "There are colleagues of mine [who] when they're sketching ask celebrities for autograph," she complains. "It's so upsetting. Celebrities don't want to be in court. For an illustrator… it's the height of bad taste!" (She has, however, spoken to celebrities a few times in court because they're friends with her brother.)

Celebrity subjects do pose their own challenges. For one, they look different in person. According to Edwards, Halle Berry and Catherine Zeta Jones both look more beautiful, whereas Alec Baldwin's face morphs. "From inch to inch, from turning his head, [Baldwin] looked totally different," Edwards recalls of his early 2000s divorce from Kim Basinger." But she finds Clint Eastwood "fabulous to draw because he's got the nose and the eyebrows. It's the person's face."

Edwards struggled to draw Gwyneth Paltrow because she appeared at her stalker's trial without her mask of makeup. She looked pale and wan, instead of chipper and healthy, and wore what Edwards describes as "a beige sweater, a symphony of beige."

"It's a stalking case," Edwards says. "The jury is supposed to feel sorry for someone. If she came in looking like how you see her photographer in the tabloids or fashion shoots, it's not very sympathetic."

Britney Spears did not need to try to appear vulnerable at her many court hearings throughout 2007. "I drew Britney in a couple of different ways," Edwards remembers. "There was one time where she looked so horrible and scared. Her nails were all chipped. She had a weird wig on her head. She looked so alone. Then she got better and her family was there."

Regardless of how miserable or happy Spears appeared, Edwards faithfully captured her likeness. "Courtroom illustration is not portraiture, and it's not cartooning," she says. "It's the essence and the soul of something."