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This Woman Will Stop At Nothing to Work for Adam Sandler

Charlotte Jolley’s latest bid to get hired at the comedian’s film company is a Hollywood billboard campaign

Like so many in Los Angeles, 23-year-old Charlotte Jolley has a showbiz dream: She wants to work for her comedy idol, Adam Sandler. Also like many drawn to the entertainment capital of the country, she faces long odds to realize her great ambition, and will do anything to stand out.

Which is why she’s rented billboards around the city, hoping to catch her future employer’s eye.

Having graduated from Texas A&M University in 2020 and arrived in Hollywood last summer, Jolley wasted no time getting her feet wet. She’s built up experience in production, writing and stand-up, she tells me, and currently works on a YouTube series — all of which could make her a valuable addition to Sandler’s film company, Happy Madison. “If I could emulate anyone’s career,” Jolley says, “it would be Adam Sandler’s. When he was my age, he was on SNL. He started his own production company where he employs all of his friends […] he has his own stand-up career.” She also admires him on a personal level. “Throughout this process, I’ve talked to hundreds of people, trying to get the best direction and the best way to go to get this in front of Adam Sandler’s eyes, and not a single person has said anything bad about his character, which means something — especially in Hollywood,” she says. 

When Jolley refers to “the process,” she means the long-term effort to make herself known to Sandler, which began in August 2021, with the storyboarding of a fan video. In the final product, she can be seen dressed up as various iconic Sandler characters from movies including The Wedding Singer and The Waterboy, as well as Sandler himself, in typically oversized cargo shorts and a Superman T-shirt. She’s on the Walk of Fame with a sign encouraging drivers to honk if they love Sandler. And we catch glimpses of Jolley as a girl watching classic Sandler fare. Growing up on his comedies, she tells me, have given them a strong nostalgia factor.

Encouraged by coworkers and friends all over — her family moved around a lot when she was a kid — Jolley had a strong community to support her every time she wanted to give up on her pitch. A second video she made includes personal endorsements from many of them. She even pulled together a crew to visit high-traffic areas in L.A. to hand out flyers with a QR code that brought up the link to her YouTube page. But that, she says, proved a tough sell, and she had problems on the digital side as well, like a glitch that caused TikTok to remove the video. She wasn’t pulling the engagement she needed to break through. And some frustrations were the stuff of classic Hollywood. At one point on a job she learned that someone from Happy Madison would be dropping in, “so I compiled this whole letter all day,” she says, only to miss her opportunity to hand it off. She was also rebuffed at the Netflix offices, where she showed up in business casual attire, QR code flyer in hand. “I think they thought I was trying to be an actress and cheat the system,” she tells me.

Meanwhile, there were the negative comments. “Especially online,” she notes, “people feel like they can say whatever they want to say because one, they’re hiding behind a screen, and two, they don’t even think that you’re a real person, basically.” It’s only honed Jolley’s desire to prove the skeptics wrong. It was in a period of defeat several months ago that she had the inspiration for the billboards, on a trip to Hawaii, where she was born. “I wanted to clear my head and see some family friends, whatever,” she explains. “My friend and I were in the middle of nowhere, in Maui, and we overhear this guy say something like, ‘You know, Adam Sandler was here like 12 hours ago.’” 

She struck up a conversation with the man, who confirmed that Sandler had just the day before been over from the island of Oahu, where was filming. Jolley, who had come to the Pacific to decompress from the “failure” of the Sandler project, took it as a sign to continue.

Back on the mainland, Jolley designed and launched her new round of advertising, five billboards throughout West Hollywood that feature her winking face and a confident promise: “Adam Sandler, I’m going to work for you.” They’ve been up for two weeks, and she’s pleased by the analytics on how many people are visiting her website,, reading her story and watching her videos — thousands of visitors in all. 

But what does she ultimately hope to do at Happy Madison? One day, of course, she’d like to be acting in front of the camera, or in a writers room. She “may or may not have” penned a script outline that she’d love to pitch to Sandler’s team. “But I recognize I may have to start off being the person who gets coffee or cleans the toilets,” she says. “Which is fine with me, it’s more of a foot in the door.” In this way, Jolley sounds like the antithesis to every Boomer stereotype about younger generations that “don’t want to work” and will never go the extra mile to make something happen.

But perhaps it’s natural to be more determined when you’re looking to collab with your hero. When I ask Jolley what her favorite Sandler movie or role is, it’s a long list. “Rom-com-wise, would definitely be 50 First Dates. I love that movie, I love him and Drew Barrymore, as well as in The Wedding Singer.” As for his funniest role, she cites Bobby Boucher of The Waterboy, along with the eponymous hero of Happy Gilmore. “It’s really hard, though, they’re all great!” she protests, adding Billy Madison and Little Nicky to her favorites.   

At last, I had to wonder what Jolley might say to Sandler if she manages to meet him. “Probably, ‘Check out,’” she answers with a laugh. “But I would also probably tell him that he has helped shape me into the person that I am, even though he doesn’t know of my existence. He just showcases that you can achieve that caliber and level of fame and success and still remain a grounded and humble person, just a good person. And someone I aspire to be more like.” 

It’s something I, for one, did not consider when I was Jolley’s age: That just as important as what you aim to accomplish in life is who you hope to do it with.