Adrian's Top Five
My top five road trip albums
A month ago, my family and I ventured into the Southwest for a puppy. We drove 1,700 miles over two days, our tires touching some of the same asphalt Sal and Dean drove in Jack Kerouac’s On the Road. A stretch of our road trip also coincided with the iconic Route 66’s centennial anniversary. It was a puppy-fueled, Americana weekend.
Once a journey is designed, equipped, and put in process, a new factor enters and takes over. A trip, a safari, an exploration, is an entity, different from all other journeys. It has personality, temperament, individuality, uniqueness. A journey is a person in itself; no two are alike. And all plans, safeguards, policing, and coercion are fruitless. We find after years of struggle that we do not take a trip; a trip takes us.
John Steinbeck, Travels with Charley: In Search of America
Twenty-five hours in a car, you have a lot of time to think, talk, and listen to music. We are a family of music aficionados, so it was only natural for each of us to come prepared with albums and playlists for the road trip. Each of us has our preferences, and so when my teenagers needed a break from Dad’s music, they put on their headphones and drifted off to their own music memories.1 Since my children are more playlist creators than album listeners, we had fun alternating between the two. Playlists are a part of their generation, the way mixtapes and burning CDs was mine. When we gifted them a Spotify account, they spent hours adding their favorite songs to a single, massive playlist. Now that they are older, they have developed talents for curating songs for different occasions.2 Over our two days of driving, I loved taking turns sharing music with my children and accepting their musical offerings.
Here are my top five road trip albums, with my wife’s and children’s favorite picks, too.
5. Hopes and Fears (2004) | Keane
When Keane’s debut album, Hopes and Fears, was released in the summer of 2004, I was teaching during the day and working in Barnes and Noble’s newly created music section at night. I had never heard of this band from the UK (touted as the next Coldplay), but Somewhere Only We Know was part of B&Ns in-store soundtrack, mixed in with Adult Alternative, folk, jazz, and classical music. Think Sarah McLachlan, Jack Johnson, Enya, Corinne Bailey Rae, and Norah Jones on a repeat loop until closing. My job was to unbox and restock CDs, and to feature the albums playing at the store’s listening stations. I had never heard anything like Keane; they were a rock band with no guitars, layered piano front and center, and Tom Chaplin’s killer vocals. I immediately purchased Hopes and Fears and it became one of my 2004 summer staple CDs. Twenty years later, Hopes and Fears is still a great album. Whenever I am stuck in traffic or have about an hour’s worth of driving, I play the album. 10/10, no notes.
4. Little Creatures (1985) | Talking Heads
There is something about the Talking Heads sound that makes a great soundtrack to the start of a journey, especially Little Creatures, their sixth album. Opening with And She Was, David Byrne’s Hey! is one of the most recognizable openings to any 80s song. Start to finish, Little Creatures is perfect driving music. I used this album to introduce my children to Talking Heads because it is the most approachable. The lyrics make more sense than on Speaking in Tongues, the melodies are catchy, and the music video for And She Was is just strange enough to intrigue my teenagers into wanting more. As we drove and listened, I watched David Byrne’s voice settle over them. Every time I looked in the rearview mirror, I saw smiles on their faces. It is impossible to listen to this album without smiling.3 Plus, the final track, Road to Nowhere, has the best build. It feels like the opening of a Sunday Sermon! Fun fact: the album cover was drawn by self-taught folk art legend Rev. Howard Finster. If you look closely, there are twenty-six Bible verses scattered throughout the painting.
3. Cat Stevens Greatest Hits (1975) | Yusuf Islam
I take my fatherly job as music influencer to my children seriously. I can trace my own musical tastes to both of my parents. My mom’s obsession with blasting ABBA whenever we ran errands may have been embarrassing, but as an adult, I am chuffed that she shamelessly listened to whatever she wanted to. My dad’s taste in music ranged from ZZ Top to The Doobie Brothers and The Moody Blues. It only seems fitting that I continue this tradition by playing Cat Stevens for my own children.
I love Cat Stevens’ Greatest Hits so much, I stole my dad’s CD when I left home for college. Now going by the name Yusef Islam, he is one of the most prolific singer-songwriters of the 70s. Listening to songs like Wild World, Father And Son4, Peace Train, and Morning Has Broken was not a new experience for my teenagers. I often listen to Cat Stevens after a long day of teaching while I am making dinner. Start to finish, this is a no-skip album that made an hour of driving go by quickly. Last year, Yusef released a new Greatest Hits compilation, On the Road to Findout: Greatest Hits, spanning his 58-year recording career. I think I may need to buy this boxset on vinyl so that my children will have something to steal from me when they leave home.
2. Greatest Hits (1976) | Tom Petty and the Heartbreakers
I will forever associate Tom Petty with the summer after my parents’ divorced. I spent the summer helping my mother move into her new apartment in Southern California. I was fifteen, bored, broke, and could not drive anywhere. Unpacking boxes, I found Tom Petty and the Heartbreakers’ Greatest Hits. Suddenly, my lonely summer was not so bad. I had Petty’s American rock canon, my favorites including American Girl5, Runnin’ Down A Dream, Free Fallin’, Learning to Fly, and Into the Great Wide Open. What makes this particular Greatest Hits album such a great road trip listen is Tom Petty. His driving guitar hooks capture the feeling of the open road. I admit, when I played this album for everyone in the car, I wanted to roll down the windows and just cruise.
1. Pet Sounds | The Beach Boys
Pet Sounds recently celebrated its 60th birthday. Surviving band members, Mike Love, Al Jardine, Bruce Resnikoff, and Bruce Johnston all attended the 60th Anniversary6 at the Capitol Records building on May 11, 2026. Rolling Stone Magazine puts Pet Sounds at number 2, just behind Marvin Gaye’s What’s Going On. Many consider this Pet Sounds to be one of the best albums of all time. In fact, Pet Sounds was Tom Petty’s favorite album and influenced much of his own music. Pet Sounds (especially Brian Wilson) even influenced The Beatles, inspiring Sgt. Pepper’s Lonely Hearts Club Band.
Legend has it that Wilson wrote most of Pet Sounds in his head by the time the rest of the band returned from a tour. Wilson desperately wanted to evolve away from The Beach Boys’ surf-rock image, and so he imagined using orchestral instruments and unconventional sound effects like bicycle bells, Coca-Cola cans, and barking dogs.
I love the whole Pet Sounds record. I got a full vision out of it in the studio. After that, I said to myself that I had completed the greatest album I will ever produce. I knew it. It was a spiritual record. I wanted to grow musically, to expand our horizons and do something that people would love, and I did it.
Brian Wilson
I can listen to Pet Sounds on repeat for hours. I never tire of it. I think I listened to it five times on our road trip. Brian Wilson says that the experience of recording Pet Sounds was spiritual. As I drove through the Southwest ruminating, this album was often playing. It is my quintessential road trip record for that very reason. I lose myself in the harmonies and lyrics. God Only Knows is the best pop song ever recorded.
Our road trip was quite an experience, made even more special because of our shared soundtrack. I got the opportunity to learn more about my children’s preferences in music. We often listen to and talk about music as a family, but being in a car for two days, I better understood why they like certain songs and artists. Nothing beats road trip bonding! Music has a way of connecting people. Each album I shared came with a story (I am a teacher, after all!), letting me take my children on a tour of my childhood. Each song they shared meant something to them, and after the thirty hours we spent together in the car, we emerged a closer family, better connected through music.
Have a great week!
— Adrian
What artists, songs, albums, or playlists do you crank up in the car on long road trips?
On Monday, June 8, I am joining four education Substackers for a FREE webinar built around the idea that teachers deserve better support, and that we are better together. Hosted by SEMH Education’s Kieran Smith, we plan to share what we write about, highlight posts, answer questions, share free resources for helping teachers improve, and offer glimpses of future projects.
Resources
This video is fascinating! Marty Music interviews Nicole Richard, a neurologic music therapist and professor from Belmont University to talk about how music affects our brains and stirs up memories, evoking strong feelings of nostalgia.
If you have not watched any of Rick Beato’s videos, you are missing out. He is incredibly knowledgeable about all things music. My favorite is his video series, What Makes This Song Great? In the above video, Rick Beato counts down his favorite one-hit wonders of the 90s. Watch until the end because he has some surprises! Want to explore a different decade? Here is Beato’s Top 20 One Hit Wonders of the '00s and Top 20 One Hit Wonders of the '80s.
10 Albums That Are Practically Summer Road Trip Essentials | Buzzfeed
I am a sucker for Top 10 lists. I love seeing what other people think is important, especially in how they rank books, movies, and music. This Buzzfeed list is decent; it reminded me of some great albums and artists that I had not listened to in a while (Paramore’s After Laughter and Bruno Mars’, An Evening With Silk Sonic).
10 Pitchfork Staffers on Their Favorite Driving Albums
This list is interesting. I love how personal it is to Pitchfork’s staffers. I love the stories that accompany each album recommendation. Mark Richardson’s idea to listen to Bob Dylan’s box set Biograph from start to finish while he drove from Grand Haven, Michigan to the Detroit Metro Airport is quite an accomplishment!
13 Best Road Trip Albums for Every Leg of the Journey by Emma Singer | purewow
The intriguing part of this list is how Emma Singer chooses albums for different parts of a road trip. Need an album for night driving? Try Ramblin’ Man by Hank Williams. Which album is best for driving in the country? The Band by The Band.
In 2025, NPR Music’s Stephen Thompson and Lars Gotrich curated their own road trip playlist. Even if you don’t like every song, this playlist has a little bit of everything for everyone. And, it is already made for you. Just press play!
If you do not like NPRs Road Trip Mix, try this one from Rolling Stone Magazine. They picked songs that “are all about forward motion, propelling you down the road and into the future” and songs that “celebrate the very fact of being alive in a car, because a good road trip is worth celebrating.” It is quite the eclectic mix!
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The scientific term is Music-Evoked Autobiographical Memories (MEAMs).
One of our favorite family games is Game That Song and they are very good at it!
Or to listen to Stephen Colbert gush over them.
Yusef rerecorded Father and Son for its 50th anniversary. The new version has Yusuf now singing the role of the father brought together digitally with a recording of his 1970s self singing as the son – taken from a recording at the legendary Troubadour Club, Los Angeles. The effect of the two generations of one man duetting with himself is deeply moving.
Again, such a great album opening! Drummer Stan Lynch provided a Bo Diddley-inspired backbeat with Petty’s intro riff. The combination is addictive. If you listen carefully, what may sound like a 12-string guitar was really two six-string guitars played by Petty and guitarist Mike Campbell. Petty layered the guitars on top of each other and Campbell left the third out of several chords, making it sound in tune and creating a horn-like sound.
For audiophiles and Beach Boys devotees, Capitol Records is releasing The Pet Sounds Sessions Highlights, a commemorative collection of a cappella versions of the songs, tracking sessions, new liner notes, and a Vinylphyle Edition of Pet Sounds cut from original mono and stereo analog tapes.
We’re doing a road trip across Oregon after school gets out next week. I’m going to institute a “no skips” album rule for music. TP-Wildflowers, U2 Achtung Baby, and FM Rumours will be in the mix.
I think I vibes most with your wife’s playlist (especially The Chicks and Simon and Garfunkel), but also YES to Tom Petty. Perfect summer/roadtrip music.
I’ll have to check out the other 4 albums.