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Route 66 Playlist: 13 Artists Rockin’ the Mother Road

I have had a lifelong love of music. For me, music is memory and memories make us who we are.

"Route 66" Is the Ultimate Road Song

"Route 66" is one of the most recognizable pop songs released since World War Two. It's been covered by hundreds, if not thousands, of artists in multiple genres. The reason for the song's popularity isn't difficult to decipher. People love road movies, and road songs are a musical variation on the formula.

In fact, the lyrics read as a travelogue about the major stops along the 2,248-mile-long route: Chicago, St. Louis, Joplin, Oklahoma City, Amarillo, Gallup, Flagstaff, Winona, Kingman, Barstow, San Bernardino, and Los Angeles.

13 Songs That Tell the Story of Route 66

So, I want to take a look at 13 different artists representing the 13 different stops along the Mother Road.

  1. Ground Zero: Various Artists, “(Get Your Kicks on) Route 66”
  2. Chicago: Eddie Harris, "Cold Duck Time"
  3. St. Louis: Chuck Berry, "Route 66 (Swing Version)"
  4. Joplin, MO: Charles McPherson Quintet, Live at Dizzy's
  5. Oklahoma City: Flaming Lips, "Bad Days"
  6. Amarillo, TX: Big & Rich, "Fake I.D."
  7. Gallup, NM: Navajo Healing Song
  8. Flagstaff, AZ: R. Carlos Nakai, *Canyon Trilogy*
  9. Winona, AZ: Wynonna Judd, "Simply the Best"
  10. Kingman, AZ: Kris Kristofferson, "Me and Bobby McGee"
  11. Barstow, CA: Jay Farrar, "Barstow"
  12. San Bernardino, CA: Frank Zappa, "San Ber'dino"
  13. Los Angeles: Natalie Cole, "Unforgettable"

1. Ground Zero: Various Artists, “(Get Your Kicks on) Route 66"

Bobby Troup wanted to be a songwriter in Hollywood, so in early 1946, he and his wife Cynthia loaded up their Buick and set off from Pennsylvania to California. Their trip began on Highway 40, but they picked up Route 66 to shift southwest.

Bobby's original idea was to write about Highway 40; it was Cynthia who came up with the line, "Get your kicks on Route 66." They wrote the song as they traveled and added the finishing touches when they reached Los Angeles.

Troup eventually worked in the city's jazz scene, supplementing his music career with appearances on TV and in movies. He had a small part in the film M*A*S*H* (1970), in which he spoke the last line, "Goddamned Army."

Shortly after that, Troup and his second wife, Julie London, starred in the TV drama, Emergency!, a gig that lasted for seven seasons. And yet, despite these many accomplishments, Troup will forever be known as the "(Get Your Kicks on) Route 66” guy.

"Route 66": Rock 'n' Roll Standard

When Bobby and Cynthia Troup wrote the song, they couldn't have imagined that Nat King Cole would take it to #3 on the race records chart (what they called R&B in less enlightened times) and #11 on the pop charts. A couple months later, Bing Crosby recorded a version with the Andrews Sisters that rose to #14.

"Route 66" stayed in the public consciousness because artists kept recording it. In the 20th century alone, the following artists recorded the track:

  • Troup himself (1957)
  • Louis Jordan (1958)
  • Chuck Berry (1961)
  • Louis Prima (1961)
  • Rolling Stones (1964)
  • Them (1965)
  • Tom Petty and the Heartbreakers (1978)
  • Eddie Hazel (1983)
  • Depeche Mode (1987)
  • Replacements (1987)
  • Buckwheat Zydeco (1990)
  • Cramps (1994)

The Group That Made the Song Famous: King Cole Trio

The King Cole Trio recorded "Route 66" on March 15, 1946, within weeks of the song being written. As I noted earlier, it was a massive crossover success at a time when Black music and White music were largely segregated.

It's easy to forget now because Nat King Cole presents such a relaxed, uncontroversial figure, but he was a pioneer for Black musicians. As it happens, later in 1946, he began broadcasting King Cole Trio Time, the first radio program hosted by a Black man.

Eleven years later, Cole again broke the race barrier by hosting The Nat King Cole Show on NBC TV. The show ran for 42 episodes, but it was cancelled because sponsors were leery about associating with a Black entertainer.

2. Chicago: Eddie Harris, "Cold Duck Time"

Since 1933, the starting point of Route 66 has been Jackson Boulevard at Lakeshore Drive in Chicago. So, we're going to begin our journey west there, in a city with a strong musical tradition that serves as a hub for great musicians even today.

A hundred years ago, Chicago was critical to the development of jazz, arguably America's first significant musical art form. The origin of the word "jazz" is unclear, but according to jazz historian Lawrence Gushee, New Orleans musicians first heard the word being used in Chicago to describe their music. In fact, the first use of "jazz" in print was in 1916, when jazz as a genre description was already well-established in Chicago.

Our artist representing the Chicago jazz tradition is Eddie Harris. Born in the Windy City in 1934, Eddie was an accomplished tenor saxophonist and keyboard player whose "Freedom Jazz Dance" was famously covered by Miles Davis for his 1967 album, Miles Smiles. He was overshadowed in the 1960s by saxophone legends like John Coltrane, Sonny Rollins, Wayne Shorter, and Stan Getz, but Harris found a niche by combining jazz, funk, and R&B.

Eddie Harris was the first to introduce an electrically amplified sax, and he invented several instruments in the 1970s: a trumpet with a saxophone mouthpiece (reed trumpet), a saxophone with a trombone mouthpiece (the saxobone), and a combination of guitar and organ (the guitorgan).

3. St. Louis: Chuck Berry, "Route 66 (Swing Version)"

If you motor west of Chicago, you eventually arrive at the Mississippi River and the Gateway to the West: St. Louis. Route 66 has been realigned in and around the city over the years, but I-44 approximates much of 66 between St. Louis and Springfield.

St. Louis also happens to be my wife's hometown and where I was once a regular visitor. Whenever I was in town, I made a point of going to Delmar in The Loop to visit a wonderful second-hand bookstore, then crossed the road to have beers at Blueberry Hill. This iconic bar serves great food and is a shrine to Chuck Berry, who played there over 200 times. Regular live music makes Blueberry Hill a must-go venue.

Born in St. Louis, Chuck Berry is known as the "Father of Rock and Roll" for turning R&B into guitar music with badass solos and memorable storytelling. Without Chuck Berry, there would be no Beatles, Rolling Stones, Dylan, or Hendrix—or, they would exist, but sound far less interesting. When the Rock and Roll Hall of Fame was established in 1986, Chuck was one of the first musicians to be inducted.

4. Joplin, MO: Charles McPherson Quintet, Live at Dizzy's

Near the Ozark Mountains, Joplin was an important center of lead and zinc mining and still shows evidence of its industrial past. Bonnie and Clyde hid out in Joplin for a few weeks in 1933. Escaping after a shootout, they left behind a camera that contained now-famous photos of the pair.

Sadly, Joplin is known as much for tornadoes as anything else. The town was hit by a massive tornado in 1971, resulting in one death and 50 injuries. However, the EF5 tornado that hit Joplin on May 22, 2011, killed 158 people (including eight indirect deaths), injured 1,150 others, and caused almost $3 billion in damages.

Charles McPherson is an alto saxophonist like his idol, Charlie Parker. He was born in Joplin in 1939, but he grew up in Detroit and came up in that city's jazz scene. He moved to New York City in 1959 and is most associated with legendary bassist Charles Mingus, with whom he worked on and off for 14 years (1960–74).

5. Oklahoma City: Flaming Lips, "Bad Days"

Route 66 in Oklahoma is now known as the Will Rogers Highway, named after native son, Will Rogers. Unfortunately for 66, its route was basically taken over by Interstate 44, which is mostly a toll road, and Interstate 40 west of Oklahoma City. That said, there's actually over 400 miles of Route 66 in Oklahoma, the second most of any other state.

Think Oklahoma and you probably think cowboy culture. In the 1930s and '40s, when Bob Wills and the Texas Playboys were one of the biggest bands in the country, they basically lived in Tulsa, ruling the roost at Cain’s Ballroom and radio station KVOO. OKC is also the home of the American Banjo Museum.

But, Oklahoma City boasts a population of almost 1.5 million in its metro area (20th largest in the U.S.), and its modern musical history is surprisingly diverse. Leon Russell, J.J. Cale, The Gap Band, Hanson, Chainsaw Kittens, Angelical Tears, and The All-American Rejects all hail from Oklahoma.

The most important Oklahoma band of the last 30–40 years are The Flaming Lips, who formed in OKC in 1983. They started out as psychedelic noise punks, but singer and principal songwriter Wayne Coyne learned to incorporate melody and song structure into the noise. By the late '90s and early '00s, the Lips had evolved into symphonic pop.

6. Amarillo, TX: Big & Rich, "Fake I.D."

In Amarillo, we're about an hour's drive away from the midpoint of Route 66, which lies in Adrian to our west. From Adrian, it's 1,139 miles back to Chicago and the same distance to cover before we reach Los Angeles.

My one and only visit to Amarillo was a brief stop on the outskirts on a trip to New Mexico. My wife and I stopped at a store to pick up Trivial Pursuit cards to help pass the time. To our surprise, these replacement cards belonged to the Canadian edition, which caused some consternation—and the realization that we had a lot to learn about Canada.

We are now firmly in country music territory. John Rich, our artist representing Amarillo, was born in the city. He was part of Lonestar before starting on a solo career and then joining up with Big Kenny to form Big & Rich.

7. Gallup, NM: Navajo Healing Song

Route 66 ran east–west across central New Mexico, along the path now taken by Interstate 40. However, until 1937, it took a longer route via Los Lunas, Albuquerque, and Santa Fe, now roughly New Mexico State Road 6, Interstate 25, and U.S. 84.

Gallup was a popular center of operations when Hollywood Western movies were in their heyday. The small city was founded as a railhead in 1881 and sits on the edge of the Navajo reservation, although tribes like the Hopi and Zuni are represented here, too.

Since we are passing through their land, it's only fitting that we listen to some traditional indigenous music.

8. Flagstaff, AZ: R. Carlos Nakai, Canyon Trilogy

The Flagstaff area had a wagon trail to California in the 1800s, but by 1886, Flagstaff was the largest city on the railroad line between Albuquerque and the west coast.

In the 1920s, local businessmen lobbied hard for Route 66 to pass through the city, and they succeeded. 66 changed the local industry from lumber to tourism, and downtown Flagstaff was essentially born.

In 1930, astronomer Clyde Tombaugh discovered Pluto at Lowell Observatory in Flagstaff, the first object discovered in what later came to be identified as the Kuiper belt.

R. Carlos Nakai is of Navajo and Ute descent and was born in Flagstaff in 1946. He began playing a traditional Native American cedar flute after an accident left him unable to play the trumpet. He has since received 11 Grammy Award nominations for his elegant, mesmerizing flute music.

9. Winona, AZ: Wynonna Judd, "Simply the Best"

No disrespect to the town of Winona, but it's a very small place. If it weren't for the railroad, it probably wouldn't be there at all. It was once also known as Walnut, a name that wouldn't have suited the song's needs at all.

Winona holds the distinction of being the only town out of sequence in "Route 66." It was a small settlement east of Flagstaff that might have been forgotten, if not for the lyric, "Don't forget Winona," written to rhyme with "Flagstaff, Arizona."

Fortunately for our musical ride, Wynonna Judd, the famed country singer, took her stage name from the mention in our song.

10. Kingman, AZ: Kris Kristofferson, "Me and Bobby McGee"

Kingman is not a big place, but it makes a big deal of Route 66. In fact, the Arizona Route 66 Museum is located on the second floor of the Powerhouse Building, and it tells the history of Route 66 through vehicles, photographs, artifacts, and even a one-hour documentary.

Kingman is also the birthplace of Miki Garcia, Playboy's Playmate for January 1973, but I decided that featuring her would probably be a breach of copyright and break our theme.

Monte Hellman's cult movie, Two-Lane Blacktop (1971), was largely shot in and around Kingman. The movie stars Warren Oates, James Taylor, and Beach Boy Dennis Wilson, and its soundtrack includes Kris Kristofferson singing his composition, "Me and Bobby McGee." A tenuous connection, I know, but it's a great road song.

11. Barstow, CA: Jay Farrar, "Barstow"

Barstow is a hot, dusty outpost in the Mojave Desert. The town's roots lie in the rich mining history of the Mojave Desert following the discovery of gold and silver in the Owens Valley and in mountains to the east in the 1860s and 1870s.

Before the advent of the interstate highway system, Barstow was an important stop on both Routes 66 and 91. The two routes met in downtown Barstow and continued west together to Los Angeles.

"Barstow" appears on Jay Farrar's mournful 2001 album, Sebastopol. As drummer Matt Pence (Centro-Matic) plays a languid beat in 3/4 time, David Rawlings plays a keening lap steel, and Gillian Welch sings high harmony. Farrar speaks for many who've driven through this arid city:

"By the time we make it to Barstow
We'll be more than halfway to hell"

12. San Bernardino, CA: Frank Zappa, "San Ber'dino"

The Route 66 Rendezvous was a 4-day, 3-night, classic car show that encompassed 35 blocks of downtown San Bernardino and ran from 1990 to 2012.

In 2012, the San Bernardino Convention & Visitors Bureau lost its funding from the city, so a 2.0 version of the event was unveiled in 2013. The Rendezvous Back to Route 66 is only one day and doesn't cover 35 blocks, but it continues to celebrate classic cars and Route 66.

"San Ber'dino" is based on an actual experience. In 1964, Zappa spent 10 days in San Bernardino County Jail because he made a fake sex tape at his recording studio and the sheriff arrested him on a trumped up obscenity charge. He was ultimately given a six-month sentence, with all but ten days suspended, plus three years probation. Even worse, the sheriffs confiscated 80 hours worth of tapes and returned them erased.

13. Los Angeles: Natalie Cole & Nat King Cole, "Unforgettable"

Route 66 ends—or begins, depending on which way you're driving—in Santa Monica, California. But in the song, the Mother Road "winds from Chicago to LA."

So, in Los Angeles we'll turn off our engine and reflect on our unforgettable trip by coming full circle. Let's listen to Natalie Cole (born in Los Angeles) duet with her own father through the magic of technology. "Unforgettable" won three Grammys at the 1992 Awards: Record of the Year, Traditional Pop Vocal Performance, and Arrangement Accompanying Vocals.

Fun fact: Natalie also recorded "Route 66" for Unforgettable... with Love, the 1991 album (a tribute to her father) from which "Unforgettable" comes.