Britney Spears in "(You Drive Me) Crazy"
Photo: Jive Records

After Britney Spears established herself as a pop-star Lolita in her video for "... Baby One More Time," the singer slowed things down a bit with her single "Sometimes." But she didn't leave her dancing shoes off for long. In the kitschy "(You Drive Me) Crazy," Britney showed the world that she's not just a sexy schoolgirl; she can be a sexy waitress too!

"Actually, the concept of the video is all my idea," Spears told MTV in 1999, adding that she thought the choreography would be "big." "It would be cool to be in a club, and we're dorky waitresses, and we break out and start dancing."

In an interview in 1998, Spears explained that she thought "Crazy" was an extension of her breakout hit, "... Baby One More Time," which makes sense, since both were written and produced by Max Martin.

"It's an uptempo [song]," she said. "Kinda like '... Baby One More Time,' same feel a little. A bit of rock in it."

Nigel Dick, who also directed "... Baby One More Time," said that although it was extremely easy to work with Spears on the video, it wasn't as easy to convince Adrian Grenier to make an appearance in it. Since the song was on the soundtrack to "Drive Me Crazy," Grenier and co-star Melissa Joan Hart were supposed to be featured in the clip as well.

"The big issue is that Adrian Grenier did not want to be in the video," the director told MTV News. "So, I was given instructions to ring him up and make sure he appeared in the video. I said, 'You know what, Adrian, I just think it would be great for your career, and Britney's a great girl and she's fun to work with.' Eventually he came around."

Given that Grenier and Hart mostly just stand around and look cute in the video as Brit and company dance around them, it's unclear how much it did for their careers. But Spears clearly hoped that the large scale and quality of the dance production would give her a boost. "I honestly think this video will hopefully take me to the next level," she said in 1999.

Dick fondly recalled working with the singer on the clip, but added a little-known piece of trivia about the video. "That 'crazy' sign is still there. It was still hiding behind something," he said. "Britney came to the set completely rehearsed. Certainly whenever I worked with her, she had an extraordinary work ethic, which I was always impressed by."