The music video for "(You Drive Me) Crazy" was directed by Nigel Dick, and shot at the Redondo Beach Power Station in California from 14-15 June 1999. Britney revealed the concept was her idea, and hoped that the video would "take [her] to the next level". Actors Melissa Joan Hart and Adrian Grenier make cameo appearances on the music video, since they were promoting the film Drive Me Crazy on 1999, which featured the song as its theme. Dick revealed that, at first, Grenier didn't want to be on the music video. "The big issue is that Adrian Grenier did not want to be in the video. 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".
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