Britney Spears had been grappling with her budding adulthood when she released her third album, simply titled Britney, in 2001. With songs like "Overprotected" and "Let Me Be," Spears seemed to be letting out her adolescent angst. But on the single "I'm Not a Girl, Not Yet a Woman," which was also featured on the soundtrack for her flick "Crossroads," the singer wanted the world to know that she was ready to be treated like an adult.

For the video, director Wayne Isham just wanted to have Britney out in nature — even if the setting seemed a bit dangerous for a pop star. "I go, 'Let me check it out first,' " Isham told MTV News about having Britney stand on the edge of a cliff. "She understood that if my fat ass was out there and I could stand there, then she could stand there," he laughed.

The singer might have been willing to take the risk, but she still had some trepidation about standing on a cliff. "The wind started picking up a lot and almost dropped me over," Spears recalled. "And I was like, 'OK, gotta go.' "

Nonetheless, Isham loved the way the video looked and said there was no green screen involved. "She went out there and, without a safety cable, just stood there with those cowboy boots on," he said. "She was standing on the edge in her cowboy boots, looking hot. We'd be right on the edge, and she had not a blink of fear."

Spears said in 2001 that the song was actually intended for the "Crossroads" soundtrack before she included it on her album. "The song was written for the movie once we had the decision to make the music part of the movie," she said. "It's an inspirational song, and it's probably one of my favorite songs that I've ever sang."

And the video is one of Isham's favorites too. "I have nothing but positive things to say about my experience with her and what she's doing right now," he said. "She stepped into it with positive energy. She ended up stepping out and kicking ass."

With the release of Britney Spears: The Singles Collection, MTV News is looking back on the pop star's career through interviews with video directors, music-industry insiders and Spears herself, as she reflects on some of her greatest hits. Keep coming back for all things Britney, and let us know your favorite Brit songs, videos, memories and more in the comments below — and if you think you're Britney's biggest fan, enter our contest to win a free copy of the album!