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"Sixteen Blue" is a song of teenage confusion, awkwardness, boredom, and anxiety. Basically, it's an accurate portrayal of the teenage experience. The unromanticized take on the subject would have been easy for songwriter and Replacements frontman Paul Westerberg, who was 25 when he wrote it and still had his ear close to the ground of that world. The Replacements fanbase were largely teens, and Replacements bassist Tommy Stinson was 16 when this song was recorded.