A Route 66 Playlist Worth Cruising To

When the weather transitions past the colder months to the warmth of summer, it motivates people to get out of the house and take a trip. You can hit up the beach or hike the mountains. But sometimes, you don’t want to be that active. Sometimes you just want to cruise or take a road trip. What better way to experience a number of states in one stretch than through Route 66?  Route 66 runs from Chicago, Illinois, through Missouri, Kansas, Oklahoma, Texas, New Mexico, and Arizona before finishing in Santa Monica, California. The whole route is 2,448 miles (or 3,429 kilometers) and can take anywhere from 30-40 hours to drive. With tons of fun places to stop along the way, geared toward folks driving it, there’s plenty to experience. Road trips are incomplete without a great playlist, so we’ve put together a list of songs that relate to Route 66 and how they relate.  

The playlist encompasses all eight states that are driven through, starting in Chicago, Illinois, and ending in Santa Monica, California. Each state will have five songs with artists that are from the area or are about the state itself. As much as I’d like to create a playlist that would carry you through all of Route 66, that would be around 30-40 hours, and no one wants to read a list of that many hours of music (and some awesome ones already exist like this one that’s 38 hours). Let’s get started at the entrance to Route 66 – in Chicago! 

Illinois (Chicago) 

“Don’t Let Me Cave In” - The Wonder Years 

The Wonder Years are part of the essential core of pop punk in Chicago, and “Don’t Let Me Cave In” references places within Chicago, such as Logan Square and The Sears Tower.  

“Chicago Is So Two Years Ago” - Fall Out Boy 

Another essential pop punk group from Chicago, Fall Out Boy’s discography is full of references to The Windy City, but you can’t get more Chicago than “Chicago Is So Two Years Ago,” speaking on the comfort of the lights of the city. 

“Sweet Home Chicago” - The Blues Brothers 

There are many versions of this classic blues song, including one by Chicagoans Ramsey Lewis, with the original being credited to Robert Johnson. The Blues Brothers version is a fun one to highlight for a playlist like this one.  

“Angels” - Chance the Rapper ft. Saba 

Chance the Rapper is a proud Chicagoan, and his nonprofit, SocialWorks, provides locals access to mental health care year-round through an initiative called My State of Mind. “Angels” pays tribute to Chicago, where he was born and raised.  

“Chicago” - Frank Sinatra 

Sinatra sings a joyful song about his love of Chicago, his hometown. You “lose the blues” leaving Chicago, but Frank Sinatra’s voice can comfort you as you begin your journey along Route 66.  

Missouri 

“Missouri Waltz” - Johnny Cash 

We can’t leave out the state song! First published in 1914, there are many versions of the song from artists/groups like The Victor Military Band, Henry Burr & Albert Campbell, and Earl Fuller. Yet despite its many versions, many of the most popular versions don’t even come from people originally from Missouri. So, while Cash isn’t from the state, his cover is a great one for a road trip. 

“St. Louie” - Nelly 

Nelly speaks on what it’s like to live in St. Louis, Missouri, with lyrics referencing places in the city. Some of those lyrics include, “Catch me in the Galleria, Plaza, or Chesterfield/Rollin' down Hanley Hills in a black Sedan Deville” and “Natural Bridge and Kingshighway is where I'm goin'.” 

“Missouri on My Mind” - Roman Alexander 

Country singer Roman Alexander represents his pride in Missouri with his song “Missouri on My Mind,” which is an ode to not only the state but also Missouri University (MU) and its football team, The Missouri Tigers.  

"Missouri Uncompromised" - Pat Metheny 

This instrumental by Pat Metheny is a great track to cruise to. “Missouri Uncompromised” was inspired by Missouri, obviously, Metheny’s home state. It’s also a reflection on the musical influences he absorbed during his youth.  

“Route 66” - Chuck Berry 

I had to include this song in here somewhere. Not doing so would have been a crime! That said, there are many versions of this song, but Chuck Berry’s is the best for the playlist because he is actually from Missouri. The song is, just as the title says, all about driving Route 66.   

A bonus artist you can throw onto the playlist from Missouri is Chappell Roan. “The Giver” has been described as a track going back to her Missouri roots. The chorus is an earworm you’ll never get out of your head (and that’s absolutely a compliment).  

Kansas 

“Song for America” - Kansas 

As you traverse the United States, why not throw on a song that explores American history, both before and after European colonization? And of course, if you’re driving through Kansas, you’ve got to listen to some Kansas. Folks disappointed “Carry On My Wayward Son” wasn’t the song selected, can add it into the rotation too. 

“This One’s for the Girls” - Martina McBride 

McBride grew up in Kansas and has expressed a deep love for her home state, but there isn’t a song to pull from her discography that is about the state of Kansas. So instead, here’s one of her songs that’s a good song to cruise to. While the title says it’s for the girls, it can be for anyone to jam and enjoy. 

"Q.U.E.E.N." - Janelle Monáe 

This Monáe track directly references their home state, Kansas, with the line “Whether in Savannah, Kansas, or in Atlanta,” which is meant to flex her impact no matter the place. That self-assured confidence is something any playlist needs for good vibes. 

“Undo Me” - Jennifer Knapp 

Jennifer Knapp released an album in 1998 that’s named after her home state of Kansas, of which “Undo Me” hails. She is one of the first and most well-known Christian music artists to come out as gay in the 2010s. The song is about a desire to be freed from constraints. Even if religious music is not your thing, you may still vibe with Knapp’s Sheryl-Crow-esque vocals.  

“Campfire Kansas” - The Get Up Kids 

This song embodies the feeling of camping in the summertime. It’s simply about enjoying nature and making the most of everything, and since they’re from Kansas, they’re most certainly talking about life in the Kansas wilderness. You can add their cover of “Home on the Range” as a bonus since it’s one they covered to help promote Kansas tourism.  

Oklahoma 

“I Ain’t in Checotah Anymore” - Carrie Underwood 

This Underwood song reminisces about what her life was like before she became the famous country star she is today. In it, she references details about the city of Checotah, Oklahoma, where she grew up. You won’t be driving through Checotah on Route 66, so you can miss the city with Underwood as you drive through the Sooner State. 

“Oklahoma Sky” - Miranda Lambert 

While Miranda Lambert didn’t grow up in Oklahoma, she owns property and has a connection to the state. At the time of the song’s release, she had married an “Okie,” as she phrased it (her ex-husband, Blake Shelton). While she says she’ll always love Texas, “Oklahoma Sky” was an ode to her new home state.  

“Take Me Back to Tulsa” - Asleep at the Wheel 

Asleep at the Wheel is also not from Oklahoma, but they have a deep connection to the state, clearly since they’ve covered a song about the city of Tulsa. Fun fact: Tulsa is actually the official capital of Route 66 (here’s the proof). The song is about not being ready to grow up and face the world.  

“Dirty Little Secret” - All American Rejects 

Multi-hit rock band All American Rejects got their start in Stillwater, Oklahoma, where it was difficult to break out if you’re not performing covers, but they managed to get their big break. There aren’t any songs directly about Oklahoma, so one of their greatest hits will have to be slotted in.  

“No U in Oklahoma” - Reba McEntire 

Reba McEntire sings of a relationship that only brings heartache, so when there’s no “U” in Oklahoma, she’s relieved she gets a break to try to heal. Born and raised in Oklahoma, it’s nice to think the comfort from the bad relationship isn’t following her to her home state. 

A bonus Oklahoma-themed song is a recent release, “Out of Oklahoma” by Lainey Wilson, which was written for the 2024 Twisters soundtrack.  

Texas 

“Deep in the Heart of Texas” by Gene Autry 

This is a classic song about Texas with many versions dating back to the 1940s. That said, Gene Autry’s is the perfect vibe for a playlist like this. Toss this one on to welcome you as you pass over the Texas state line. 

“Texas Cowboy” - Michael Martin Murphey 

Country singer Michael Martin Murphey hails from Texas and often talks about his home state within his music. “Texas Cowboy" celebrates the Texas landscape and cowboy life. What’s more fitting than that for a road trip playlist? 

“Texas Blood Money” - Upon a Burning Body 

This metal track is all about the pride of Texas, and what can happen if you mess with Texas and the people from there. The song has lyrics like “Everything is bigger in Texas/loaded double barrel blow you to pieces.” This is a common sentiment when it comes to songs about Texas. It also references the song “Deep in the Heart of Texas” in its intro.  

“El Paso” by Marty Robbins 

“El Paso” tells the story of a man who falls in love with a Mexican girl who has caught the eye of multiple cowboys in El Paso, which leads to a shootout and a man on the run. The song is obviously set in Texas, but the way Robbins sings the story is also perfect to cruise to.  

“Texas On My Mind” by Pat Green 

This Pat Green song personifies the state of Texas, speaking about it as an object of love. “Texas On My Mind” captures the affection for the state, its people, and all its traditions. What could be more fitting for a section appreciating the state of Texas? 

New Mexico 

"(El Corrido De) La Prison De Santa Fe" - Al Hurricane 

Al Hurricane and his son (Al Hurricane Jr.) are two of the biggest artists associated with the state of New Mexico. Even if you don’t speak/know Spanish, you can get the vibe from any of their songs. I chose what he wrote in response to a 1980 New Mexico State Penitentiary riot.  

"Ranchera Jam" - Lorenzo Antonio

Raised in Albuquerque, New Mexico, Lorenzo Antonio has had a career with a mix of Spanish and English songs. While I couldn’t find a song directly about the state, he did do the "Ranchera Jam," which was a mashup of him performing a New Mexico-style version of Mexican staples like "Cielito Lindo" and Tito Guízar's "Allá en el Rancho Grande." 

"Santa Fe" - Beirut  

The indie folk band Beirut and their song aptly named “Santa Fe” is an ode to the place where they got their start. While they also have connections to Albuquerque, their connection to Santa Fe shines in this song.  

"Santa Fe” - Newsies Soundtrack 

How could we not include this song that longs for life in Santa Fe? Character Jack Kelly wants to escape his difficult life in New York, and Santa Fe represents his dream of a new life. He longs for a fresh start there. He sees the city as a place of freedom, hope, and opportunity.  

“My Fair New Mexico" by Morgan Miles 

This track pays homage to the New Mexico state song and has been making rounds on the local radio stations, so you may not even need it on a playlist! The song is all about celebrating the things people love about New Mexico, and the lyrics even reference Route 66: “66 is the American drive/And there’s nothing bluer than the Western desert sky.” 

Arizona 

“Big Iron” - Marty Robbins 

Yes, Robbins shows up twice on this list. He has so many great songs referencing the South, especially Texas. That said, “Big Iron” is a song that does reference Arizona, the Agua Fria River specifically, and an Arizona Ranger who has a fateful duel with the notorious outlaw Texas Red.  

“By the Time I Get to Phoenix” - Glen Campbell 

Although Campbell is from Arkansas, he has lived in Phoenix for two decades. This version of the song is a reinterpretation of Jimmy Webb’s version, which is a torch song longing for his girl he left in Phoenix.  

“Arizona” - Scorpions 

This Scorpions song is all about finding love in Arizona. The state becomes generalized as a great place because of the positive experience the singer has picking up a girl there.  

“If You Don’t, Don’t” – Jimmy Eat World 

The rock band Jimmy Eat World formed in Mesa, Arizona, and their song “If You Don’t, Don’t” isn’t about their home state, but it does reference Ninth and Ash in Tempe, Arizona. The song explores the sentiment: if you have to ask, it’s probably a no--because if you love someone, it’s instinctive.

“Everywhere” - Michelle Branch 

“Everywhere” is a song that fits well into an upbeat road trip playlist. Even if you don’t think you know this song, I’ll bet you do, as it’s playing in retail stores all the time. Michelle Branch was born and raised in Arizona, and while “Everywhere” isn’t a song about Arizona, using her to represent the state is never a bad idea.  

California (Santa Monica) 

“California” - Mazzy Star 

This Mazzy Star track fits the coastal vibes of Santa Monica, speaking of longing for California, even if it feels like a distant place. If you began your drive in Chicago, I’m sure Santa Monica did feel like a distant place, but you made it! 

“Where’s California” - Teena Marie 

This song also longs for California, referencing Santa Monica. “Where’s California” uses the city as a symbol of the California coast, a beautiful place where there’s only sunshine and happiness.  

“Tell Me Ma” - Gaelic Storm 

This Celtic band was founded in Santa Monica, California, but they don’t have songs specifically about the Santa Monica area. So instead, this playlist features one of their popular songs, “Tell Me Ma,” which is all about the joys of youth and courtship.  

“Santa Monica” - Everclear 

One cannot make a list of songs about Santa Monica without including this classic from Everclear. The song was written about the singer’s hometown. In an interview, she said about the song, “I've lived in cold places and been in bad relationships, and I think everybody has a place in their mind that is like a safe haven.” Santa Monica is that safe haven.  

“Santa Monica” - The Front Bottoms 

The Front Bottoms aren’t from Santa Monica, but they do have a song about the city. “Santa Monica” reflects on a weekend trip to Santa Monica and the narrator's realization that one shouldn’t suppress their feelings. This moment of self-realization is a great way to end the Route 66 road trip.  

Bonus: “All I Wanna Do” - Sheryl Crow is another great way to end the drive because of its feel-good vibes and reference to Santa Monica Boulevard. 

This playlist gives you at least 40 songs (with a few bonus tracks) to bump as you take your journey. We hope you get your kicks cruising through Route 66. Bring us back a souvenir! 

Written and compiled by Kristen Petronio