"Pretty Little Adriana" is a song written and recorded by American country music artist Vince Gill. It was released in October 1996 as the third single from the album High Lonesome Sound. The song reached number 2 on the Billboard Hot Country Singles & Tracks chart and won Gill a Grammy Award for Best Male Country Vocal Performance.

Deborah Evans Price, of Billboard magazine gave the song a mixed review, calling it "a little lackluster" and saying that not every song can be an "I Still Believe in You" or a "Go Rest High on That Mountain." However, she goes on to say that the song boasts "tasty guitar work, a pretty melody, and, of course, Gill's signature vocals."

"Pretty Little Adriana" debuted at number 63 on the U.S. Billboard Hot Country Singles & Tracks for the week of November 9, 1996.

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