A Brief History of the 16 Most Memorable Celebrity Courtroom Sketches, from Amy Winehouse to Taylor Swift
Taylor Swift’s trial against a radio DJ who allegedly groped her in Denver this week marked a milestone in bringing justice to women who regularly face sexism in the music industry—and, you know, the everyday world. But for some on the internet, the trial’s initial takeaway was the sketch that first emerged from the courtroom. Swift’s near un-recognizable likeness evoked veteran courtroom artist Jane Rosenberg’s viral 2015 depiction of Tom Brady, though Swift’s portrait has been less meme-y. Depicting a celeb once on trial has also become something of a curious art form. Some, like the prolific Mona Shafer Edwards, have devoted their life to it: Originally a fashion illustrator, she gave up runways for courtrooms decades ago, and has portrayed everyone from Paris Hilton to Lindsay Lohan to Michael Jackson in their respective court appearances ever since. Indeed, back in the ’80s, when Edwards was sketching Dolly Parton, the singer told her she was such a fan of her work in the bathroom that she asked to buy one, wrote a check, and then proceeded to use the stall. Not every celeb, of course, is an admirer of these hastily sketched portraits: Martha Stewart even reportedly scouted out potential artists ahead of her trial in 2004, and kept such close watch on the images that she reportedly recognized one of her least favorite sketchers in the audience at a taping of one of her shows—and called them out as a “bad artist.” Revisit Martha’s likeness, plus other memorable ones of Amy Winehouse, Michael Jackson, and others, here.
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Though Denver’s court system somehow managed to assemble a jury who’d maybe never listened to Taylor Swift for her groping trial this past week, the whole world seemed to know that the sketches that emerged from the courtroom bore little to no resemblance to the pop star—other than her preference for Peter Pan collars. Indeed, the real artist behind the sketch was Jeff Kandyba, but some joked that it was likely instead Katheryn Hudson—the birth name of Swift’s nemesis, Katy Perry.
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Note that Mona Shafer Edwards took care to capture the red soles of Lindsay Lohan‘s Louboutins when the actress was led away in handcuffs in 2010, to await a hearing on whether she violated her probation (for drunken driving and cocaine possession) by failing a drug test.
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This sketch of Martin Shkreli, the “Pharma bro” who’s been widely hated since 2015, was depicted by the same artist responsible for the infamous depiction of Tom Brady. This time around, she seemed to incorporate the public opinion about Shkreli ever since he raised the price of a lifesaving drug by more than 5,000 percent into the sketch—no doubt appreciated by the jury, who’s so far reportedly called him both a “snake” and a “dick.”
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After Paris Hilton showed up late to her 2007 Beverly Hills trial in an uncharacteristic pinstripe suit, but before she was convicted of violating her probation, the early 2000s icon actually pulled out her compact and started doing her makeup in court—a moment Edwards benevolently chose not to depict.
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In 2009, Amy Winehouse was accused of assaulting a fan and ultimately acquitted—after the singer, just 5’3″ in her ballet flats, stood up to remind the judge of her small stature and stand by her claim that she only could have been defending herself.
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Edwards depicted Michael Jackson in court in 1996 for a low-key case (one regarding the Jackson Family Honors show, and his failure to sing alone, without his family, onstage), and she also again captured him in 2005, when he faced charges for molesting a teenager. Though he’d worn a red jacket before, here, the wan singer wisely left his flashy looks at home—though he does sort of resemble an accurate mix of Voldemort and a Gryffindor.
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In 2015, Pharrell Williams took part in an eight-day trial with Robin Thicke whose jury ultimately decided that their single “Blurred Lines,” which made $16 million in profits, borrowed just a little too much from Martin Gaye’s “Got to Give It Up.” Evidently, he took the trial very, very seriously: It was one of the only time he took care to leave his trademark camo blazers and murses at home.
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Edwards was also there at the trial to depict Robin Thicke, and indeed, her sketch of the singer was heralded by some as the only good thing about the entire case. After all, to not have commemorated the moment Thicke pulled out a keyboard on the witness stand and sang a medley of U2’s “With Or Without You,” The Beatles’ “Let It Be,” Alphaville’s “Forever Young,” Bob Marley’s “No Woman No Cry” and Michael Jackson’s “Man in the Mirror” would have been a crime in and of itself.
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Martha Stewart famously went on trial—and eventually went to prison—in 2004 for obstructing an investigation into her stock sales, but chief in the domestic goddess’s mind throughout the process were also her portraits during the trial; she even courted sketch artists ahead of time, and got the Wall Street Journal to switch out its rendering where she thought she appeared bloated. Though this sketch by alum Rosenberg was apparently passable, another courtroom frequenter, Shirley Shepard, wasn’t so lucky: When Shepard showed up to a taping of her show three years later, Stewart allegedly pointed her out to the audience—and declared her a “bad artist.”
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Edwards was also there to capture the original modern-day courtroom celeb, Winona Ryder, when she went on trial for shoplifting $5,560 worth of items from Saks Fifth Avenue in 2002. The $760 cashmere Marc Jacobs sweater she took was nowhere to be found in court, though; a subdued Ryder, who did not testify, kept it mum in the courtroom and also kept her look subdued.
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After winning two Emmy Awards for her courtroom sketches, Ida Libby Dengrove went on to depict Sex Pistols frontman Sid Vicious when he was infamously accused of murdering his late girlfriend, Nancy Spungen, who was found stabbed with a knife belonging to Vicious at the Chelsea Hotel in 1978. Whether you’re team Sid or Nancy, the incident clearly took a toll on Vicious: Here, he looks much older than his early twenties.
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Even on crutches, Halle Berry still stood out when she showed up to her custody battle with her ex Gabriel Aubry in 2012, in part because of another accessory: a flashy apparent engagement ring from her then-partner Olivier Martinez, whom she ended up marrying the next year.
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Hidden from Edwards’s depiction of an at-ease Dolly Parton at her 1985 trial for charges she’d copied much of her hit “9 to 5” is not only the fact that the singer was wearing stilettos, but also that she told Edwards she loved her drawings in the bathroom—and even wrote her a check to purchase one before heading into the stall.
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Like his newfound buddy, Martha Stewart, Snoop Dogg has also spent time in the courtroom, though back in 1996, when he was known as Snoop Doggy Dogg, it was hardly a laughing matter: Along with his bodyguard, he was charged—and ultimately acquitted—of murder, after the shooting death of a gang member, hence his uncharacteristically subdued demeanor.
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Thanks to her abusive ex Chris Brown, Rihanna has also found herself spending time in the courtroom. Brown had purple hair at the time that he pleaded guilty to his felony assaults against the singer in 2009, while Rihanna remained stony-faced—and dressed in head-to-toe black.
