A bittersweet recollection of carefree days full of laughter and dancing in the rain, Matthews describes this as a happy but "desperate-sounding" song.
This features backing vocals by The Lovely Ladies (Tawatha Agee, Cindy Myzell, and Brenda White King), a decision producer Steve Lillywhite regrets. DMB had never featured prominent female voices on their songs before, so Lillywhite wanted to give it a shot. "They still to me sound very much overdubbed and out of place," he noted in a 2018 interview with the podcast Records & Riffs.
This is the fifth track on the Before These Crowded Streets album, appearing as a bright spot between the darker tunes "Don't Drink The Water" and "Halloween." Lillywhite, who took charge of the track order on the albums he produced for DMB, says the placement was essential: "'Stay' needed to be put further in the album to bring you up a little bit."
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