If you were watching late-night TV back in October 2009, you probably remember the moment Jay Leno pulled out a giant cardboard cutout on The Jay Leno Show. It was Chelsea Handler in Playboy. Or, well, a version of her.
At the height of her Chelsea Lately fame, Handler wasn't just another celebrity looking for a career boost through a centerfold. She was already the queen of E!, known for a glass of vodka in one hand and a biting Remark about a Kardashian in the other. When news broke that she’d be gracing the December 2009 issue, people expected the "full Chelsea." What they got was a bit more complicated—and a lot more on-brand for her.
The 2009 Cover: A Vodka-Soaked Christmas
Most people assume that if you're a woman on the cover of Playboy, you’re bare. Not Chelsea.
For the December 2009 newsstand issue, Handler appeared in a gold string bikini and matching boots. Another version of the cover—the one sent to subscribers—actually featured Dancing with the Stars alum Joanna Krupa. Chelsea’s version was specifically a "newsstand only" treat.
Inside the magazine, the vibe was pure comedy. She did a "20 Questions" interview, which is standard Playboy fare, but the photoshoot was the real talk of the town. One specific shot featured her in a mini-dress and an apron, "preparing" a vodka-soaked Christmas meal. She wasn't alone, either; her late sidekick, Chuy Bravo, was right there in the mix.
"I'm not naked on the cover," she told Leno during that awkward 2009 reveal. She even joked that her dad would love it because he thought she was "very sexual." Honestly, that’s such a Chelsea thing to say. She also admitted that to get in "Playboy shape," she had to quit drinking for about a day and a half.
Why the Photoshop Drama Mattered
During the Leno interview, things got a little spicy. When Jay unveiled the cover, Chelsea looked at it and basically called out the retouching immediately.
"We'd need the guy who airbrushed me to come back," she quipped when asked to recreate the pose. It was a rare moment of a celebrity being totally transparent about the "Playboy polish." Most stars at the time tried to pretend they just woke up looking like a matte-finish goddess. Chelsea? She wanted you to know she’s a real person who likes snacks and booze.
The 2016 Return: Not a Photoshoot, but a Statement
A lot of fans forget that the most impactful time Chelsea Handler in Playboy became a headline wasn't for a bikini shot. It was for her writing.
In 2016, Handler returned to the magazine—this time for the "Freedom" issue. She wrote a deeply personal, incredibly raw essay about her teenage years. This wasn't about "the best body" or being a pin-up. It was about her choice.
In the essay, Handler revealed she had two abortions when she was 16 years old.
- The Cost: She noted it cost $230 at Planned Parenthood.
- The Reality: She was honest about the fact that she was "irresponsible" but argued that she wouldn't be the woman she is today without the right to choose.
- The Takeaway: She famously wrote, "It's a wrap on men deciding what women can do with their bodies."
This shifted the narrative. Suddenly, her relationship with Playboy wasn't just about a 2009 holiday-themed gag. It was a platform for a serious political and social stance. She used the magazine’s history of "sexual revolution" to talk about actual bodily autonomy.
The Nudity Paradox
Chelsea has always had a weird relationship with being naked. She’s famously posted topless photos on Instagram to protest their double standards—often comparing herself to a shirtless Vladimir Putin on a horse.
She once told Ellen DeGeneres that she likes to be naked because she doesn't take her body seriously. "I think bodies are so silly," she said. This explains why her 2009 Playboy appearance felt more like a comedy sketch than a seduction. She wasn't trying to be a "Playmate" in the traditional sense; she was playing the character of a Playmate.
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What Most People Get Wrong
There's a common misconception that Chelsea did a full-frontal spread. She didn't.
While she has been nude for Allure and basically all over her own social media for years, her Playboy stint was relatively "covered up" compared to the magazine's usual standards. It was "Playboy Lite."
- The Timing: It happened right as she was becoming a household name.
- The Sidekick: Chuy's inclusion made it a comedy piece, not just a glamor shoot.
- The Audience: It was a clever marketing move for Chelsea Lately.
Why It Still Matters Today
Looking back from 2026, the Chelsea Handler in Playboy era represents a specific moment in pop culture. It was the bridge between the "old" Playboy (the one focused purely on the male gaze) and the "new" version that tried to incorporate more voice and personality.
Handler’s 2016 essay, in particular, remains a cited piece of work in the ongoing debate over reproductive rights. She didn't just use her body to sell magazines; she used her history to start a conversation.
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If you're looking for the original 2009 issue, you'll find it on eBay for anywhere from $12 to $30 depending on whether it's the "Chelsea cover" or the subscriber version. But the real value isn't in the paper. It's in the way she refused to play the game by the usual rules.
How to Navigate Chelsea's Legacy
If you want to understand the impact of Handler's work with the brand, don't just look for the photos.
- Read the 2016 Essay: It's available in digital archives and provides a much deeper look into her "why."
- Watch the 2009 Leno Interview: It’s a masterclass in how to handle (and mock) the industry's obsession with airbrushing.
- Follow Her "Free the Nipple" Activism: Her Playboy work was just the starting line for her career-long battle with social media censorship.
Next time you see a celebrity "breaking the internet" with a "candid" shoot, remember Chelsea did it back in 2009 while holding a glass of vodka and a turkey. She made it okay to be both "sexy" and "hilariously human" at the same time.