When The Sweetest Thing was released in theaters back in 2002, the raunchy comedy helped pave the way for Bridesmaids, Girls Trip, Bad Moms, and more.

The Sweetest Thing opens with a series of men describing Christina Walters (Cameron Diaz) as a heartless player navigating San Francisco’s singles scene. A successful 28-year-old interior designer, Christina avoids commitment and treats dating like a game. She and her best friend Courtney Rockcliffe (Christina Applegate), a sharp-tongued divorce lawyer, take their recently dumped roommate Jane Burns (Selma Blair) out clubbing to lift her spirits. There, Christina tries to set Jane up with Peter Donohue (Thomas Jane), but he calls her out for her manipulative tactics. Though Christina insists she’s unaffected, Courtney notices Peter clearly rattled her.

Christina later reconnects with Peter at the club, and the two share an easy chemistry. He explains he’s attending his brother’s wedding and is celebrating with his obnoxious sibling Roger (Jason Bateman). Peter invites Christina and Courtney to an after-party, but she declines and immediately regrets it. The next day, unable to stop thinking about him, Christina learns the wedding is in Somerset. Convinced this could be something real, she and Courtney impulsively road-trip to find him, enduring increasingly absurd mishaps involving exploding toilets, sexual misunderstandings, and public humiliation.

Meanwhile, Jane begins seeing a new boyfriend (Johnny Messner), leading to her own chaotic sexual misadventures. Christina and Courtney eventually arrive at the wedding in outrageously gaudy outfits after ruining their clothes along the way. Christina hesitates about interfering, but after bonding with the bride, Judy Webb (Parker Posey), she decides to attend. In a twist, Peter turns out to be the groom, not Roger. Their presence contributes to the realization that neither Peter nor Judy truly wants the marriage, and the wedding is called off.

Back home, life resumes. Courtney begins dating a doctor, Jane’s relationship escalates into another emergency, and Christina slips back into her detached routine. Eventually, Peter tracks Christina down after finding her address at the store where she and Courtney shopped. Though he initially echoes the earlier interviews by labeling her a player, he ultimately reveals they reunited and married. The Sweetest Thing reframes Christina not as a user, but as someone who finally allowed herself to risk vulnerability and commitment.

When I first saw the comedy in 2002, I was in my late teens and still presenting as male, but that’s a longer story. I made the decision to rewatch the film just under two months before its 24th anniversary in part because of wanting nostalgic viewing and in part because I’m working on writing my memoir about growing up a straight Jewish woman through a media lens of movies, TV, and music. Seeing The Sweetest Thing at that age felt aspirational in ways I didn’t yet have language for. Who didn’t want to be living a life like Christina, Courtney, or Jane?!? It was formative in ways I didn’t even realize at the time.

Studio-backed raunchy comedies centered on women were nearly nonexistent in 2002, so films like The Sweetest Thing were just unheard of. And when someone finally wrote the film, it really pushed the boundaries to the point in which things were cut due to discomfort. Not because of the filmmakers but because of studio executives. Would Universal have kept it in had they won the bidding war? I don’t know. Screenwriter Nancy Pimental, who had written for South Park at the time, didn’t have a hands-on approach during filming like most writers do today. She wasn’t on set to explain what her intentions were for a scene.

It’s a dire shame that “The Penis Song” was cut out of The Sweetest Thing and placed in the unrated version. They already had a few other musical numbers in the film, including “I Don’t Want to Miss a Thing” when trying to loosen Jane’s mouth from her boyfriend’s piercing on his penis, which was really a banana. Nobody’s agent wanted their client to have their mouth stuck on a penis, but Blair is one of the few who was willing to do it because of working with Diaz and Applegate. Unfortunately, the actress had really bad TMJ and it was painful to film on her part.

There are multiple scenes in movies that are just unforgettable. You have the musical numbers. The dry cleaners. You have the bathroom where Courtney gets splashed across the room with water and Christina gets poked in the eye by a penis. Mind you, it’s the men’s bathroom so who knows what was really going on there. Jane gets to have sex with her boyfriend while he’s wearing a purple elephant costume! Christina goes down on Courtney as a biker looks on. I love how committed Diaz, Applegate, and Blair were to the film because The Sweetest Thing is not what it is without them. It’s ridiculously absurd and I just love it.

Watching it now, what strikes me isn’t just how far it pushed the envelope but how free it felt. The Sweetest Thing let its women be loud, vulgar, romantic, delusional, and sincere all at once. As a teenager, I didn’t yet understand why that freedom resonated so deeply. Rewatching it now, I do. The film wasn’t just raunchy. It was permission.

DIRECTOR: Roger Kumble
SCREENWRITER: Nancy Pimental
CAST: Cameron Diaz, Christina Applegate, Selma Blair, Thomas Jane, Jason Bateman, Parker Posey

Columbia Pictures released The Sweetest Thing in theaters on April 11, 2002. Grade: 4.5/5

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