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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.
As we become entrenched in adulthood, we tend to idealize youth and forget what a mess of uncertainty and confusion those years actually are, a time when we try to assert our individuality while feeling painfully uncertain of who we even are to begin with. We're trying to adopt our expected roles while letting go of the old ones we'd just gotten comfortable with. It's a tenuous time of transition.
"Sixteen Blue" captures the awkward pride of it all.
“Brag about things you don't understand
A girl and a woman, a boy and a man
Everything is sexually vague
Now you're wondering to yourself
That you might be gay”
The way that the verse jumps erratically from idea to idea sums up the herky jerky 16-year-old mind perfectly.
Let It Be is the album on which Westerberg's songwriting took a quantum leap forward in skill and maturity. We can see that in this song.
Westerberg enjoys shoveling snow because it reminds him that he's just a guy, not a rock star, when all is said is done. His insistence on staying humble and grounded in reality comes through in the clarity of observation in "Sixteen Blue."
Online rumors float around that this song is about Replacements bassist Tommy Stinson (best known to modern music fans for his 1998-2014 Guns N' Roses run), who helped form the Replacements when he was 12 years old. The rumor is understandable because Stinson is the subject of other Replacements songs and because he would have been 16 at the recording of "Sixteen Blue."
While nothing can be written off definitively about the rumor, there aren't any sources to confirm it, and it doesn't add up outside the fact that Stinson happened to be 16. The song sounds much more the story of a typical 16-year-old male, not one who started living the rock-and-roll lifestyle at 12 and never knew anything else after that.
Writing for The Boston Phoenix (September 21, 1990), journalist Tim Riley called this "the greatest ode to the dignity of adolescent inferiority since 'Every Picture Tells A Story.'"
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