Simon's first wife was Peggy Harper, and they had a son in 1972 whom they named after her maiden name. In 2009, Harper Simon cut an eponymous album, and he invited his father to participate. Together, they wrote three songs, and the first one on the album is this one.
It's autobiographical, from the speaker's standpoint, although in the third line, he adds the caveat: "Most of it is true."
The first line, however, is "Howdy," and in the country-flavored song, the speaker describes how he identifies more with his mother-- he's "proud [his] mama comes from Tennessee"-- instead of New York City, where he was born and raised. (Harper himself was born and raised in New York, but I was unable to determine if Peggy was from Tennessee.)
He says she is, specifically, from Newport, "a place of moderation, common sense, and decency." While he has moved to her home state, he hasn't achieved that style of behavior, just as yet: "It's nothing like the way I am/ But it's how I'm gonna be."
So, how has he been, then, thus far? Well, he was "kicked out of" several schools, received many "incompletes" and finally "bought a C," by which he means bribed his teacher to give him a passing grade, or perhaps paid a student to take a test for him. (At this point, we know the song is not autobiographical to Harper, at least as far as he left out the part where he attended the prestigious Berklee College of Music.)
Next, the speaker says he"rambled around/ from Slumberville to Lonesome Town," which might be the locale of the Heartbreak Hotel.
At some point, he got bitten by the musical bug. He "joined a band" which proved unsuccessful but, undeterred, "booked some time on Nashville's Music Row." He tried to use music to connect to his Southern roots: "Don't want no electric guitars in the background."
Now, this plan is a work in progress. "I got issues/ I got pain," ("issues" being typically New York word) he admits, "There's a lot I can't remember/ Even more I can't explain" (this couplet is pure country, however).
See, he's "trying to concentrate on how you find serenity/ When you're born in New York City/ But your mom's from Tennessee." He feels that the bustle and shallowness of New York might be what has made him feel aimless, so his theory is that if he can-- through music-- reconnect with his traditional past, perhaps he can find both physical and emotional stability.
Perhaps by connecting with his roots through roots music, he can finally feel, well, rooted.
Paul sings harmony on this track, and played guitar on others on this album.
Many "ringers" were brought in as backups. A very good list is available at Harper's Wikipedia page; ones from the rock world include drummer Steve Gadd, and Steve Nieve, one of Elvis Costello's Attractions. It can be assumed that Paul was responsible for the presence of some of them, but Harper had been playing professionally for some time and it would be unfair to assume he had made no musical friendships of his own. In fact, there seem to be at least three generations of musicians here.
Next Song: Ha Ha