When The Sweetest Thing first opened in April 2002, it earned less than $9.5 million at the box office and picked up a 32 Metascore from critics. The rom-com centered on a woman named Christina (Cameron Diaz) who is sick of playing dating games but still stuck self-sabotaging went on to earn a little more than $69 million worldwide in ticket sales and release an "unrated" version on DVD and streaming that features an original song about penises.

Twenty years later, The Sweetest Thing is a bona fide fan favorite and trend-setter for audience members who recognized themselves and their friends in the clever banter Christina had with her besties Courtney (Christina Applegate) and Jane (Selma Blair), and enjoyed the raunch-filled road trip as Christina and Courtney traveled the California coast on a mission for love. 

"It didn't do well initially in the box office, which was disappointing in a lot of ways, but it is very, very weird how it, still to this day, has a cult following, and I still get people on a very frequent basis who contact me that they're watching it again or it's their favorite movie," screenwriter Nancy M. Pimental tells Metacritic. "This guy emailed me a couple of days ago, in fact, and he said, 'Two of my best friends, it's their favorite movie and they both have tattoos of a piña colada glass on their arms.' It had an interesting impact on people."

The specific impact likely varies depending on which character the viewer connects with most. Some may have been immediately drawn to the Sex and the City-esque opening sequence of Christina's previous paramours recounting their negative experiences with her, which spoke volumes about their own flaws, in addition to previewing her insecurities about the dating scene. Others may have loved the specificity of inside jokes and references the trio of women shared, as well as how they were there for each other whether one was sad over a recent breakup or literally stuck in a precarious position with a new beau. Others still may have connected with the dance around the new men to enter their lives, from Thomas Jane's Peter, a love interest for Christina who came with a surprise twist, to the quintessential questionable club-goers, including Johnathon Schaech's four-word speaking Leather Coat Guy and Jason Bateman's Roger (who happens to be Peter's lying brother).

The fact that the film, directed by Roger Kumble, has endured through the years may be somewhat bittersweet to Pimental, who was working as a staff writer on Comedy Central's South Park when she began working on the script for this, her first feature film. Originally designed to be a calling card for her comedic sensibility, the final result strayed from her intentions, which makes reflecting on its success a complicated endeavor for the now-industry veteran, who most recently wrapped Showtime's Shameless after 11 seasons.

"I have such mixed feelings about it because I feel like what I wrote versus what ended up getting executed, there's a little bit of a gap in tone," she says. "I have a hard time just being gracious and just saying 'thank you' to people because I feel like if it had stayed more tonally what I had wanted, I guess I'd be curious what kind of reception that would have."

Here, Pimental talks to Metacritic about her inspiration for The Sweetest Thing, what pieces of the film are very different than how she imagined them, and whether she would do it all again if given the chance.

How much of the inspiration behind writing The Sweetest Thing was to fill a void for female-focused content you saw in the industry while you were working on South Park, which, arguably, was being marketed toward a more male-dominated demographic?

My career has never been about that. I didn't actually ever think, "I'm going to show women in a different light and that's my intention." My career has never been gender driven. I try to present as talent not as gender, so it wasn't like, "Ooh, I need to balance the male-dominated South Park" because I didn't feel that way.

What first sparked the idea for the film then?

We were on a hiatus from South Park, but we were still getting paid for South Park — I always say I got paid by South Park to write The Sweetest Thing. Those guys were really focused on the movie, and I was taking a bunch of meetings, and I'll tell you what the catalyst was for me: Ivan Reitman wanted to meet me, may he rest in peace, and I went up to Montecito because that's where he met everybody, and it was the fanciest meeting I ever had. He had, like, 25 people that worked for him that he was loyal to for 25 years, and we were all sitting around the table and it was a catered lunch, and this is what they did every day.

We were having this meeting and he wanted to remake Gidget, and he said to me, "If you say yes, I'll write you a check right now. I want you to do this." And I remember saying to him, "I just don't think tonally I'm the person." And I said something like, "If I was going to do it" — and this is the first thing that came to my head — "I would want to write a spoof song in there about gonorrhea." And all 25 people were dead silent, looking at me like I was insane and totally didn't get me.

People either get you or you don't, and it's not a right or wrong thing. People were like, "He was going to write you a check right there and you walked away from it?" Yeah, I wasn't going to deliver what they want. And I remember driving home from Montecito thinking, "The only way this is gonna happen is if I just write my own thing." And I literally was like, "I'm just gonna write it so people see tonally what I would like to do." I wanted to show, first and foremost, my voice, and then yes, through through female characters that also didn't fit in that stereotypical box of, "I just need to find a man."

When things shifted in production that no longer felt like they were in your tone or voice had to make it harder for you to feel like this was still a calling card. What pieces of the film do you feel were most changed?

I have a very juvenile, 12-year-old boy sensibility and sense of humor. And I had these girls have that same kind of 12-year-old boy sense of humor in the writing. It was really just my voice and my way of how my girlfriends and I talked at the time and what I just thought was funny. But, I felt like in the execution it was more overtly sexual than I would have wanted. The penis song, the way I wrote it was very campy, very Monty Python-esque, and the way it was executed was more, "Let's do close-ups of asses and vaginas." And that's why it didn't end up in the [theatrical] version. It was too sexual, and that wasn't the tone.

How much were you on set to be able to try to advocate for your original vision?

I wasn't. I was so naive and new, and there was always such a mantra in this town that the director is king in movies and the writer is king in television, and because it was my first one, I honestly didn't know. So I kind of fell into that [belief] that the writer is supposed to be invisible.

Working for 11 years on [Shameless,] a television show where I wrote 27 episodes and I produced all of those episodes, I learned, "Oh this is how it goes." You have a concept meeting with all of the department heads and the director and the writer. And the writer talks about everything in the script [down to] "Oh, when you say an audience full of people, how many people did you imagine?" And then you have a tone meeting with the director [and] the editor where you're talking about, "What's the tone of everything?" That should have happened. I don't need to be on set. Being on set is super, super, super boring. Our job on Shameless, over seven days of prep, was to get the director ready to hand over the reins to them — that they knew every single thought in my head with every single line and every single stage direction. So did the actors because we gave the actors a chance to talk to us and say, "I don't get this line" or "I would never say that line" or whatever. None of that happened on the movie.

Talking about capturing how your friends talked to each other at the time, how much did you draw directly from your life for creating Christina, Courtney, and Jane's relationship?

I would say a lot because I was working at Le Petit Four, which was a pretty high end restaurant up on Sunset Plaza, and it was only waitresses; the the owners wouldn't hire any man. And we would get these little write ups about us [in which] they would call us the Calvin Klein model waitresses, and the owners would be like, "You need to put more makeup on. Where's your makeup!?" You could never get away with any of that crap today. But even though there was this label on all of us, I think what I really liked about it was none of us fit that stereotypical, L.A. Barbie doll, "I'm going to get a boob job so I can land a husband" persona. That's how everyone wanted to categorize us, but not one of us was that stereotype which is portrayed so often. So that was inspiration because everyone was trying to make us that, but none of us were.

In the summer time, we'd have all these Saudi princes there, and it was a lot of money and a lot of flashiness. We all knew all of them, and I still see some of those guys around; they're still doing the same hustle. I remember this one guy this one time goes, "Hey Nance, this guy" — the guy he was sitting with — "is a plastic surgeon in case you need anything." That was very much an influence for me.

That sounds like the perfect inspiration for Roger, who is the kind of guy who, if you linger on too long, you begin to wonder who would marry him. Yet, for much of the film, you have to believe he's getting married in order to follow Christina and Courtney on their jaunt up to Somerset. Did you ever have concerns about needing to soften him in moments so the audience wouldn't get suspicious that it wasn't his wedding they were going to end up crashing?

I don't know if it was me trying to create some kind of story twist so it wasn't so linear or if it actually did come in afterwards, once the studio was involved and they were giving notes, I honestly don't remember. So, I would say the inspiration was, whether it was for me or the studio, was to just not make this a travel log where we're going A to B to C. But the inspiration was to just create a little more than just, "I'm going to chase down this guy and now there's that guy." That's too linear.

How did you approach visualizing your characters while you were writing, especially considering how much you were drawing from your own friends?

I definitely had it in my mind for Cameron from the beginning. She just, for me, had that thing that I'm describing with these women that I worked with where the container might look like what you imagine a woman would be in L.A., but the inside is not. I hate to label it, but she had masculine energy in the way that she approached things.

Speaking of the way people approach things, you mentioned before that you wrote the movie based on the way you talked with your friends, and these characters do have a very specific lexicon that lends itself to extremely repeatable moments. Which ones do you get quoted to you most often?

There's always some sort of piña colada references and things like that. for sure. And then there's Leather Coat Guy — that just comes from my family because all the guys that my mother used to date, they never had names — then they'd become real. So, it was always the Old Man, the Lawyer Guy — just descriptive phrases.

After having the experience you did with this film, where the end result wasn't entirely how you pictured it, what are your thoughts on doing it all again, in a sequel or a remake fashion?

I would do a prequel, I would do a sequel, I would do a remake. Any time I have a little bit of a lull in writing and I think, "What should the next thing be?" that definitely circulates around in my brain. But it would have to be right. It should be its own thing and not taint this. I think a lot of times when people do reboots or extensions, it can overshadow a little bit of what was special. I would have to have an interesting take that could still preserve what we've already done and not bastardize it at all.

Where to watch The Sweetest Thing: