A car accident at 18 left him paraplegic. He was "discovered" by R.E.M.'s Michael Stipe, and has played with musicians as varied as Widespread Panic and jazz guitarist Bill Frisell. His discography is staggering, with a dozen albums filled with emotionally complex and beautifully simple songs.
The most recent chapter in Chesnutt's life, and his most recent album, is a collaboration with fellow Athens, Ga., band and Elephant 6 members Elf Power, who back Chesnutt's songs so naturally that Chesnutt and Elf Power have to think a bit to remember how they all began playing together in the first place.
"How did our collaboration come about?" Chesnutt repeats my question to someone in the tour van, who pauses before responding.
Turns out Chesnutt and Elf Power were asked to play together for a TV show on a station in Athens.
"It never aired," explained Chesnutt over the phone somewhere outside of Oxford, Miss., en route to New Orleans. "But then we were like, 'Hey, we rock, so let's do some recording.'"
The result was Dark Developments (Orange Twin), and in true Chesnutt fashion, it's a doozy: nine strange and catchy songs filled with poetry and power.
"It just felt really good, you know--I could tell that they were a great band," explained Chesnutt. "I'd be a fool not to play with them. They're complete popmeisters, and they rock. They're really good at their instruments, you know what I mean? I have that psychedelic aspect to my songwriting, on certain songs, and first off, I thought it would be really fun, and second off, I thought it'd be very successful."
And it is indeed successful--Dark Developments begins with "Mystery," a sort of celebratory ode to absence, or maybe complete literalness, depending on how one reads the lyrics ("absolutely no / precisely zero / mystery"), and then throws out the rocker "Little Fucker," before settling into a blend of clever folk-pop ditties like "We Are Mean," "And How" and "Bilocating Dog."
Of course, each song has a story behind it: "Little Fucker" is actually autobiographical, explained Chesnutt: It was written after the breakup of the Undertow Orchestra, a band Chesnutt was in along with Mark Eitzel, Pedro the Lion's David Bazan, and Centro-Matic's Will Johnson. "They always called me the little fucker. So when I got home from this tour, I wrote this song, because I was depressed and mad at myself, so I wrote this song about myself."
Why did the members of the Undertow Orchestra call Chesnutt "Little Fucker"?
"There is a specific reason," Chesnutt admitted. "Because we were traveling in a big van, they had to help me in it. They had to pick me up and put me in it, and every time someone would do that, I would make a noise like, eeeaaah!--like that, right, like they were hurting me, except one time, I started laughing, and they realized I was just fucking around, and then they said, 'Well, you little fucker.'"
Good stories abound on Dark Developments: There's the allegorical "We Are Mean" ("in the city we hear laughter / in the country we hear screams / in the city we are social / in the country we are mean") with its delightfully wicked chorus of, "We are mean, we are mean, we are mean!," and "Phil the Fiddler," which is actually just a list of characters ("Paul the peddler / Joe the hotel boy / The girl in the gingham dress"). On "Stop the Horse," Chesnutt sings, "If the old girl's got a gun, then we've got a problem."
Writing a great album like Dark Developments seems like it would be old hat to Chesnutt, who has been writing music for decades, but, he said, "It changes. It was really easy to make my first album, because I didn't know any better. Now, I get nervous. I feel like I'm better now than I was then, but I'm a complicated person with complicated emotions that are all wrapped up in my music-making and recording and all that shit."
He continued, "It's a yin and yang of being a veteran musician: I've got middle-aged insecurities, and I've also got middle-aged arrogance, so it's a complicated thing. I'm a Gordian knot you can't unravel except with a fucking hatchet."
Luckily, no hatchet is needed to unravel Dark Developments: With Elf Power's "popmeistery," Chesnutt's complexities end up sounding like damn good songs.