"Legend of a Cowgirl" is a song by American singer-songwriter and rapper Imani Coppola. The song reached its peak of No. 36 on the Billboard Hot 100 on the week ending October 25, 1997. Although radio airplay and sales were good, it was the elaborate music video that made the song a hit. Her next single, "I'm a Tree", only reached No. 98 on the US pop charts and was the only one after "Cowgirl" to chart, effectively making Coppola a one-hit wonder. VH1 ranked the song at number 21 on their list of "40 Greatest One-Hit Wonders of the '90s."

Among the album's tracks, the song "Legend of a Cowgirl" became a hit on MTV. According to Coppola, the rap song, which includes a sample of Donovan's "Sunshine Superman", started as an idea she had for a movie about women who "love 'em and leave 'em and ride off into the sunset." Part of Coppola's marketing included a music video for "Legend of a Cowgirl" that received heavy rotation on MTV. "It was very uncomfortable 'cause we had no room and their penises and their bums are just flopping around," says Coppola. "It was like, 'Whoops, sorry. Didn't mean to touch you!' But they were all gay, so it didn't really matter. They were cute though. It was a shame."

The video starts with a waitress in a restaurant standing in front of a door with the camera panned toward the floor. A fried pancake falls onto the floor behind her, leaving it to the viewer's imagination as to where it came from. The camera pans sideways over to Imani in the same waitress uniform pressing the play button on a huge boom box, which starts playing the subject song, visibly bored. A series of daydream sequences follow.

The first dream shows Coppola as a biker chick, wearing a leopard-print tank top with a low back and leather bell-bottoms. She rides on a motorcycle in the middle of the desert with two cowboys. She spots a guy she finds attractive, who hitchhikes a ride. She gets off her bike and kisses him on the lips while the cowboys begin to dance, and eventually they all take off. She is woken up from this dream by an old lady smoking and blowing the cigarette smoke in her face.

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