The good folks over at Ledbury asked for me to put together a road trip mix. I could think of no road finer than ol’ Route 66. You can get the whole playlist here.

I grew up on Route 66. No, really. In 2005, Missouri named the road along the backside of my parents’ neighborhood in St Louis a state scenic byway. You can now drive that road from Illinois to Kansas. With past experiences as a traveling salesman and today as I crisscross the U.S. to meet the artists, artisans, and craftspeople who are still making things in their backyards, I often find myself retracing the old haunts along the Mother Road. What I’ve found most fascinating is how this historic byway continues to inspire and instill a true sense of pride of place especially in those of us lucky enough to have called this road our home.

1) Woody Guthrie – This Land is Your Land

Mr. Guthrie was born in Okemah, Oklahoma, just South of Tulsa. As the forebear to such wonderful singers and songwriters as Pete Seeger, Bob Dylan, and Bruce Springsteen, it’s only appropriate we start out with his Anthem of America’s open road.

2) Muddy Waters – I’m Your Hoochie Coochie Man
I can’t turn the corner at Jefferson and Jackson Boulevards in my hometown of Chicago without hoping I might catch sight of a big, old jalopy, packed with everything but the kitchen sink, looking like something out of a Steinbeck novel, parked out front of Lou Mitchell’s, the best breakfast in the city (complete with a free box of Milk Duds for the ladies), and get this: it’s the start of Route 66. The city of Chicago was once synonymous with the blues, and no one more perfectly exemplified the Chicago Blues than Mr. Waters.

3) Nat King Cole – Route 66
No Route 66 playlist would be complete without this classic rendition of Bobby Troup’s song, the swingin’est tribute to the highway that “winds from Chicago to L.A.” and deep into the fabric of America.

4) Chuck Berry – Nadine
“I saw her when she turned and doubled back and started walkin’ toward a coffee-colored Cadillac. I was pushin’ through the crowd to get to where she’s at, and I was campaign shouting like a Southern diplomat.” There’s a reason they call him the Shakespeare of St. Louis. And that’s not even the best line in the song. This could be a playlist comprised solely of Chuck Berry tunes, and you’d have enough musical fuel to get you to the Pacific and halfway back.

5) Son Volt – Windfall
Mr. Jay Farrar, co-founder of seminal alt-country group Uncle Tupelo, is a native of Belleville, Illinois, a last stop in Illinois before crossing the Mighty Mississippi into the Show-Me State, Missouri. This track should be the theme song of road-weary travelers the world over.

6) J.J. Cale – Hey Baby
Having penned the classic Clapton songs “Cocaine” and “After Midnight,” Tulsa native J.J. Cale is undoubtedly a songwriting legend, but with hits like “Crazy Mama” and this classic, he’s a force in his own right. Cale’s pace is perfect for a casual drive down the rubbled remains of Route 66.

7) Joe Cocker – Space Captain
A funny thing happened in Tulsa. This English rock music impresario, responsible for producing hits like “A Whiter Shade of Pale” and “With A Little Help From My Friends,” a man named Denny Cordell, moved his operation there, set up shop with his label Shelter Records, and started inviting the best musicians in the world to move to Oklahoma. Hometown Hero, Leon Russell — who by time they met was already a seasoned session musician having worked with some of music’s finest — was enlisted to record and tour with this hardscrabble soul singer from Sheffield, England named Joe Cocker. This wacky, space odyssey, the story of a traveling man, lost and unsure how to find his way home is easily my favorite song.

8) Buddy Holly – Rip It Up
On the day the music died, we lost this rock ‘n roll legend, the man responsible for the “Lubbock Sound,” too soon. Buddy Holly’s rollicking take on this Little Richard tune always manages to find it’s way to the radio on long road trips.

9) Beirut – Sante Fe
Sante Fe native, Ben Condon, began performing under the moniker Beirut in 2006. Melodic, inventive, sweeping, this is a glorious tribute to his hometown. I love how frequently I find myself humming along to this song. “Sign me up, Sante Fe,” indeed.

10) Jackson Browne – Take It Easy
“Standing on a corner in Winslow, Arizona….” Upon hearing that iconic lyric, how many of us haven’t wanted to do just that while this tune blared from factory speakers in a vintage pick-up? In 1971, at the age of 23, Jackson Browne began writing this song, perfect for driving, but when he ran into difficulty finishing it, he gave it to his friend and neighbor Glen Frey, who finished the song, the first big hit for his new band, the Eagles.

11) Eagles – Heartache Tonight
And speaking of Glen Frey, he penned this tune with another son of Route 66, Amarillo, Texas’ very own, Mr. J.D. Souther. Can’t you feel the slow chug of L.A. traffic, dusk approaching over the Hollywood sign?

12) Billy Bragg & WILCO – California Stars
I have bookended this playlist with nods to Woody Guthrie. In 1998, at the invitation of Guthrie’s daughter Nora, Billy Bragg and Jeff Tweedy and his bandmates in WILCO took many of Guthrie’s unrecorded written lyrics adding instrumentation, creating several instant classics, none more so than this anthem to a night spent staring up into the night’s wide sky at the end of the road.

You can find the whole thing here on Spotify.

Remember when? Here’s a post on Route 66 in Illinois from the All Plaidout archives.