In the early aughts, Britney Spears set out to shed her Mickey Mouse Club persona once and for all. All roads led to Crossroads, the 2002 coming-of-age dramedy penned by a pre-Grey’s Anatomy Shonda Rhimes. The movie, which coincided with the release of the pop princess’ single “I’m Not a Girl, Not Yet a Woman,” sought to introduce a more mature star to audiences — and the attempt was not without its roadblocks.

“We definitely had to fight for some stuff,” director Tamra Davis recalls to EW more than two decades after the movie’s release. That included Spears’ PG-13 (emphasis on the PG-13) sex scene with a love interest played by Anson Mount, when that was one of the reasons why Spears wanted to do the film in the first place: to shed her girl-next-door image amidst invasive, sexist headlines about her purity.

“She wanted to [challenge] that image that she’s this forever virgin girl,” Davis explains. She adds, too, that the scene was done tastefully. “A kid would not know what the heck is going on!” the director quips. “That was a fight I’m happy we won.”

In celebration of Spears’ memoir The Woman in Me (out Oct. 24), Crossroads is cruising back into theaters on Oct. 23 and 25. In her first feature film role, Spears plays Lucy, a high school graduate who embarks on a cross-country road trip with her childhood friends, popular girl Kit (Zoe Saldana) and pregnant Mimi (Taryn Manning), to reconnect with her estranged mother (Kim Cattrall). Joined by Mimi’s mysterious and hunky pal Ben (Mount) and his ’73 Buick convertible, the girls rediscover their friendship and find themselves along the way.

Below, Davis revisits the cult classic and its memorable musical moments (hello, NSYNC sing-along), talks a potential sequel (“Shonda had an idea”), and provides a promising update on the movie’s streaming fate.

ENTERTAINMENT WEEKLY: I revisited the movie and felt like I was enveloped in a warm nostalgia blanket. What do you remember from your first meeting with Britney?

TAMRA DAVIS: I had the same feeling. I had to do all the color corrections [for the re-release] and was also moved by how nostalgic it was. When I first met her, I originally said I didn’t know if I wanted to do the film. And then my producer, Ann Carli, said, “Would you just go meet Britney?” So I spent the day with her and really fell in love with her. I thought, she really wants to do something different. I saw that she was in control of who Britney was. I was like, whoa, she is running this whole thing. And she said she really wanted to do what it took to make a film — the rehearsals and commitment and stopping all the Britney craziness and just become an ensemble member of this cast. It was like jumping in a fast car.

It came at the height of Britney and Justin Timberlake. How did that NSYNC sing-along scene come to be? Was it already in the script?

I know, it was right in the middle of the two of them together, and they were seriously the cutest couple. I would have to go knock on her hotel room door in the morning sometimes and be like, “Okay, Britney, time to go,” and Justin would be there. It was during the height of, “Is Britney a virgin?” I wasn’t even going to ask! Even waking her up in the hotel room, I was like, whatever is going on in your private life, that’s private. [Editor’s note: This interview was conducted prior to the release of excerpts from Spears’ memoir in which she reveals she had an abortion while in a relationship with Timberlake.]

The [NSYNC] scene encapsulated what was going on with the music scene at that time. It was this mixture of what music [Ben] wanted to listen to, which was Nirvana and alt-grunge, versus what the girls wanted to listen to, which was NSYNC and Backstreet Boys and boy bands. We loved that contrast of radio. I don’t know if it was specifically in the script. I think up to the last minute, we didn’t know if we would have the rights because it was a gigantic song.

Were Kim Cattrall and Dan Aykroyd top choices for Britney’s on-screen parents?

Yes, we were all obsessed with Sex and the City. That was a game-changer for all of us girls. Britney really wanted Kim Cattrall. She doesn’t really do a lot of stuff, so it was exciting that she agreed to it. It was brave of her because it’s kind of a dark thing. It wasn’t loving. It was like, you just rejected your daughter. It’s not always pretty, when you go back to find your mom and have this fantasy that she’s going to embrace you. Dan was also fantastic and warm and fatherly. I loved what he represented, and also that the film really was about trying to break that control.

And then there’s Zoe Saldana and Taryn Manning, both at the start of their careers. What was their dynamic like with Britney?

The film was cast by my sister, Kim Davis, and Justine Baddeley. They’re up for an Emmy for Daisy Jones and the Six. They’re really good at casting young talent. The chemistry between the three of them was fantastic. I wanted to surround Britney with really good talent [and] people her age, where she could be part of that ensemble and wasn’t expected to carry the movie. When I first had her, she was just coming off of gigantic tours where she was the lead, where everybody says yes to you. I think it was really liberating for her, just to be part of a group and blend in.

You’ve expressed interest in a sequel as long as the original team returns. Have you connected with any of them to discuss?

I’m currently working with Van Toffler, who was the producer on it, and he’s [mentioned it]. I think he’s been talking to Britney about it, with her management. Britney, I don’t think she really wants to act so much, but I know Ann spoke to Shonda about something, and Shonda had an idea, so who knows if that will have life. But if it does, fingers crossed that Shonda’s involved because she’s just so brilliant. You could see on her first feature film what an incredible voice she had and her understanding of female characters. We were all girls behind the camera telling this story about girls in front of the camera. It was such an important voice at that time.

Do you have any updates on the movie’s streaming status? You’ve mentioned some trouble with tracking down the rights.

I have an update. I was trying forever. I’d call MTV, I’d call Paramount, I’d call my agents. I had just seen it — I forget how many years ago — at a London film festival, and it was insane. The theater was crowded. People were singing along and I was like, this film is really important [and] should be available. And then I got a call a month ago: “Hey, they’re doing a color mix. They need you to be there to approve it.” Sony called me because Britney called and got it picked up again because she wanted it to help launch her book. One phone call from Britney and it’s available! I think that’s what they’re going to work on now, is getting a streaming deal. I’m sure we will. They’re dealing with offers now.

The movie is considered a cult classic, but at the time of release, it was largely panned by critics. What do you make of the shift?

[The reviews] made me so mad. What right did these dudes have to criticize this movie? This wasn’t for you; this was for girls, by girls, about girls. Just stay away from our dialogue [and] out of our bedroom — you’re not allowed in. If you don’t have anything to say about girls’ culture and what girls reveal, it’s not for you. I’m not commenting about Fast & Furious like that. It put us more in the bedroom. It made us lock the doors. I wanted to make a film that made Britney, my producers, and Shonda happy. At least I know we made the movie we intended. My whole career was like that: I got slammed for making Billy Madison [and] Half Baked. Those are classics now. I’m excited [Crossroads] comes back out to show what we did at a different time. We’re at a different part of our zeitgeist.

You’ve said that you had trouble getting in contact with Britney during her conservatorship since her team often blocked messages. Have you spoken to her since it’s been terminated?

I haven’t. We’re communicating through [other] people, so she knows how much I love and support her. I’m also grateful that, because she’s not out there talking, she trusts me to be out there speaking for the movie. I can’t wait to read her book to figure out what her experience was. I just wish her the best.

This interview has been edited for length and clarity.

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