He thought Nashville was the roughest, but Willie plays all sorts of songs about place.

"City of New Orleans" isn't a song about New Orleans. It's a song about a train called the City of New Orleans. Willie Nelson didn't write it. But he made it a Grammy Award-winning hit in 1984.

Looking back, it's easy to see how Willie Nelson came to it. Over the course of his career—a five-decade ramblin' run that spans recordings as far back as 1962 and as recent as last year—Willie has written endlessly about his affection for (and occasional vexation with) cities across the land.

These are all of those places. Well, a whole hell of a lot of them, anyway.

(Mark Byrnes/CityLab with elements from the Library of Congress and Wikimedia Commons/GDuwen)

No one map could track all the sites and cities Willie sings about. He's recorded songs about rivers: the Rio Grande and the Pedernales, the Mississippi and the Ohio, the Rhine and the Jordan. He's played songs about trains: the Midnight Special, the Wabash Cannonball, the Golden Rocket, the City of New Orleans. (And, of course, a song about rainbows.) Georgia, Montana, Tennessee, and Texas all loom large over his songbook.

Cities serve as metaphors and signposts in Willie's songs—a role they tend to play in much of blues, country, and folk. Maybe it's because he's a master of those three styles that he's known for songs about cities and places. That interest unites all those different genres in his catalog. The experience of traveling cross-country, getting the hell out of some place or setting off for a new start, is an entire category of Willie Nelson songs, right up there with cowboy heartbreak and drinking whiskey.

(Mark Byrnes/CityLab)

Fifty (maybe 60?) years into his professional touring career, Willie is on the road again: At 81, he's just set out on another American tour. Later this month, you can catch him playing three shows in Central Texas. With Merle Haggard. If that's not enough to get you on a red-eye flight to the Lone Star State, don't worry, he's playing dates all summer. When his tour bus rolls into Boston, or L.A., or Kansas City, or New York, he'll be playing to cities he's been singing about for decades.

The map and chart above represent a good first draft toward compiling a list of every city Willie's ever crooned about in a song. He didn't write all of them—Kris Kristofferson, Townes Van Zandt, Lyle Lovett, and other legendary songwriters have their fingerprints all over this list. But Willie made these songs his own. More than a few of them are songbook standards: Grandpa Jones wrote "Eight More Miles to Louisville" in 1946. And yet: Willie Nelson is older than this song.

Willie recorded a few iconic songs about cities by other singer-songwriters, including Dave Loggins' decidedly not-country "Please Come to Boston" or the barn-stomping swing number "Columbus Stockade Blues" (written in 1927, just six years before Willie was born). His wide-ranging selections have an almost curatorial significance. (May the Highwaymen forgive me for using Willie Nelson and "curator" in the same sentence.)

Surely these songs aren't the whole lot of Willie's songs about places. He's got more one-off collaborations and rare singles than most artists have songs total. But these songs double as a solid collection of hits, so CityLab put them all together on a Spotify playlist (save one or two). If you'll oblige us, hit play and read on for a couple stories about the Red-Headed Stranger—and how a simple song can shape how we think about a place.  

Willie Nelson plays Wilmington, Delaware, in 2014. (Owen Sweeney/Invision/AP)

"City of New Orleans," 1984, City of New Orleans

Despondent over the news that the Illinois Central Railroad passenger line might be canceled, a Chicago singer-songwriter named Steve Goodman penned the song in 1970. "The City of New Orleans" is a love note to the Amtrak train of the same name, which traveled on the so-called Main Line of Mid-America between Chicago and New Orleans. (And still does today.)

Shortly after he wrote the song, Goodman spotted Arlo Guthrie at a Chicago bar, where he asked him if he could play something for him. Guthrie famously agreed to hear him out, on the condition that Goodman buy him a beer—and finish the song in the time it took him to drink that beer. Well, Goodman landed his audition. Guthrie liked "City of New Orleans" so much he recorded it for a 1972 album.

Willie Nelson named his 1984 record City of New Orleans after Goodman's song. The single won Goodman a posthumous Grammy Award for Best Country Song the very next year. This recording is the surely the best song in history about an Amtrak train.

Willie Nelson plays Farm Aid in Louisville, Kentucky, in 1995. (Timothy D. Easley/AP)

"Kansas City," 2000, Milk Cow Blues

Wilbert Harrison, a rhythm-and-blues man from Charlotte, landed a Billboard #1 hit record in 1959 with "Kansas City." It was a traditional blues number written by Jerry Leiber and Mike Stoller, the Max Martin and Dr. Luke of their era. The Los Angeles songwriters transformed rock music with songs like "Yakety Yak," "Jailhouse Rock," and "Hound Dog." They wrote "Kansas City" for Little Willie Littlefield, a San Francisco boogie-woogie star from Texas, but it was Harrison who turned it into a gold album.

"Kansas City" has since been performed by Little Richard, James Brown, the Beatles, and Willie Nelson. Nobody from Kansas City had a thing to do with it.

Nancy Reagan, Ray Charles, and Willie Nelson in 1983 (Ira Schwarz/AP)

"Baja Oklahoma," 1988, Baja Oklahoma

Willie's song "Baja Oklahoma" isn't about a city called "Baja." The phrase is a funky way of describing Texas. Willie wrote the song for a made-for-TV movie, Baja Oklahoma, an adaptation of a novel by the same name, about a woman who dreams of seeing her name on the marquee lights in Nashville but struggles to make it work in Texas. The song now exists almost exclusively on VHS cassette and Croatian-dubbed YouTube clips.

More than anything, though, the song (and the movie) are actually about Nashville—a city that provoked outlaw country artists like Willie Nelson to rebel. But Willie almost never wrote about Nashville by name.

"Ladies and gentlemen, Willie Nelson!" George Washington introduces Nelson at a White House performance in 2014. (Manuel Balce Ceneta/AP)

"Me and Paul," 1985, Me and Paul

A rare song in which Willie does sing about Nashville is "Me and Paul," and it's one of his finest. It's a tour diary about Willie's travels with Paul English, his drummer and money man. English is known for sporting a famous cape and, well, for lots and lots of crime. He puts the "outlaw" in outlaw country: As a young man, he ran around with a bunch of hoodlums and petty thieves called the "Peroxide Gang," as Joe Nick Patoski tells it in Willie Nelson, an Epic Life, a biography. Read Patoski's writing about Willie and English, and you will come to appreciate that "Me and Paul" is the most completely sanitized song about their lives that you could imagine.

And as the song says, they probably still don't like Willie Nelson in Buffalo. Good thing they love him in lots and lots of other places.  

Willie Nelson in 1986 (AP)

Correction: A previous version of the map and chart misidentified the Boulder mentioned in “Highwaymen” as Boulder, Colorado. The lyrics reference the Boulder Dam, which is now known as the Hoover Dam.

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