I want you to picture something for a second.
Imagine you are standing in a driveway in Pennsylvania.
Okay. It's early 1946. The world is just starting
to exhale after the Second World War. Exactly.
And you're packing the trunk of a 1941 Buick.
You're loading up suitcases, double -checking
the tires, and staring at this massive paper
map that stretches all the way to the sunny coast
of California. You're chasing a massive dream.
You really are, specifically making it big as
a songwriter in Hollywood. So you turn the key,
you hit the road, and you are completely, blissfully
unaware that before you even reach the Pacific
Ocean, you are going to write a piece of absolute
music history. Which is wild to think about.
Welcome to the Deep Dive. We are jumping into
a story today that is going to completely alter
the way you hear a legendary piece of Americana.
It really is the quintessential American road
trip narrative. What we're doing today is sorting
through a massive encyclopedic breakdown of the
1946 Rhythm and Blues classic, Get Your Kicks
on Route 66. Oh, yeah. And the documentation
we have covers everything, you know. Its highly
spontaneous origins, its immediate and enduring
chart -topping history, and its incredibly strange
cultural footprint that spans across oceans and
generations. The mission for today is to trace
how a very simple map inspired tune became the
ultimate musical chameleon. Looking at a standard
that effortlessly jumped from its R &B roots
right into pop, rock, jazz, country. And even
British punk adjacent folk. Yes. OK, let's unpack
this. We have to go back to that 1941 Buick and
see what was actually happening in the passenger
cabin. Right. So behind the wheel is Bobby Troop.
He's an American songwriter and he's taking this
massive 10 day cross -country relocation. with
his wife, Cynthia. A 10 -day drive. Yeah, and
anyone who has ever done a multi -day drive knows
the highway hypnosis sets in quickly. Oh, definitely.
Your mind starts scanning for anything to focus
on. And for a songwriter like Troop, the road
itself became the canvas. But the funny thing
is, his initial idea wasn't even about Route
66. No, it wasn't. He was driving west and thought,
I should write a raid song about U .S. Highway
40. Which, U .S. 40 was a major artery, but is
a lyric. It's incredibly clunky. Yeah, it lacks
that rhythmic punch. It really does. And that
is the exact moment Cynthia Troop steps in and
alters music history because they eventually
transition off US 40 and merge onto US Highway
66. The famous stretch from Chicago down to L
.A. Right. And Cynthia turns to him and casually
pitches the title, Get Your Kicks on Route 66.
She handed him the definitive hook of his career.
Yeah. I mean, it's got that sharp. percussive
consonants, the kicks, 66. It's perfect. But
the timeline of the actual songwriting process
is what really stands out in the documentation.
Troup gets this title from his wife and starts
working out the melody and the concept during
the 10 -day drive. Literally writing it while
the tires are rolling over the asphalt. Exactly.
But he couldn't actually finish the lyrics from
memory. Wait, he drove the entire route and still
couldn't remember the towns in order? Not well
enough to write a cohesive song. It wasn't until
they finally parked in Los Angeles that he was
able to sit down at a desk, unfold a physical
paper map of the very highway he had just traversed,
and manually construct the lyrics by listing
the cities and towns along the way. That is hilarious.
He needed an atlas to finish his own diary entry.
Basically, yeah. And the best part is that even
with the map sitting right in front of him, tracing
the route with his finger, he makes a massive
geographical blunder. A huge omission. Cynthia
later pointed out her utter disbelief that he
managed to write a song cataloging their trip
and completely left out Albuquerque. He just
sailed right past it. One of the biggest cities
in New Mexico. What's fascinating here is how
that highly specific list -based lyric style
actually functions for the listener. Right. By
meticulously or almost meticulously minus Albuquerque.
Right. Minus Albuquerque. Naming these waypoints
like St. Louis, Joplin, Oklahoma City and Amarillo,
Troup isn't just writing a vague ode to travel.
He is handing the listener a tangible itinerary.
It grounds the song. You feel like you are sitting
in the backseat of that Buick watching the road
signs blur past. Exactly. So Troop is in Los
Angeles. He's got these map assisted lyrics and
he pitches it. And the song lands in the hands
of an absolute titan. Nat King Cole. On March
16th, 1946, Nat King Cole and the King Cole trio
walk into radio recorders in Los Angeles and
lay down the very first studio recording. And
Capitol Records puts it out. The context of that
release. tells you a lot about the musical landscape.
Yeah, the B -side is interesting. Right, the
B -side to this single was a track called Everyone
Is Saying Hello Again, Why Must We Say Goodbye?
Which is a classic, sentimental 1940s ballad.
Very standard for the era. But flip that record
over, and the A -side, Route 66, is a completely
different beast. It explodes. It immediately
hits number three on the race records chart.
Which we now know as the R &B charts. Yes, and
it climbs to number 11 on the broader pop singles
chart. Nat King Cole loved the track so much
that he made it a permanent fixture of his career.
He re -recorded it a few times, didn't he? He
did. Once for his 1956 album, After Midnight,
and again for the Nat King Cole story in 1961.
And we really need to pause and examine why Nat
King Cole's original arrangement. became the
bedrock for everything that followed let's do
it if you listen to that 1946 recording it is
built on a very standard 12 bar blues progression
musically speaking that is one of the sturdiest
most universally understood frameworks in Western
music. It's the architectural equivalent of a
steel frame building. You know it's not going
to fall over. Precisely. The King Cole trio took
that 12 -bar blues structure and injected it
with this incredibly tight, swinging, upbeat
rhythm. The interplay between the piano and the
guitar. It's light but driving. It mimics the
momentum of a car cruising down the highway.
By establishing it as this infectious rhythm
and blues standard right out of the gate, Cole
proved the song's structural integrity. Because
it was mathematically simple enough. Exactly.
You could speed it up, slow it down, or completely
change the instrumentation without losing the
song's core identity. Here's where it gets really
interesting. Because the moment a song proves
it has that kind of bulletproof structure, every
other artist wants to take it for a test drive.
They want their own spin on it. The genre hopping
begins almost instantaneously. In that very same
year, 1946, Bing Crosby teams up with the Andrews
sisters and drops their own version. And they
take it to number 14 on the Billboard chart.
So in its birth year, you have the pioneering,
swinging R &B of Nat King Cole and the heavily
orchestrated, tight commercial pop harmonies
of the Andrews sisters, both charting simultaneously.
It's the first proof of the chameleon effect.
And the song just keeps absorbing the cultural
shifts around it. When the rhythm and blues era
gives way to the rock and roll revolution. 1966
doesn't get left behind it gets weaponized fast
forward to 1964 the British invasion is in full
swing And a young band called the Rolling Stones
decides Route 66 needs to be on their self -titled
debut album. The music critic Richie Unterberger
has a great piece of analysis on this. He calls
the Stones take the most famous rock version
of the song. Because it wasn't just album filler.
No, it was the centerpiece of their early live
tours. They were cutting their teeth on this
American road anthem. They even released a live
version on their 1965 UK EP Got Live, if you
want it. And the U .S. The sonic shift from Nat
King Cole's smooth piano trio to Keith Richards'
gritty, overdriven guitar is massive. Completely
different vibe. But the craziest part of the
Stones' version is the actual lineage of how
they put it together. They weren't trying to
channel Nat King Cole at all. No, they were channeling
Chuck Berry. Berry had recorded a phenomenal
guitar -heavy version for his 1961 album, New
Jukebox Hits. And the Stones worshipped Chuck
Berry. They adopted his raw, aggressive rhythm.
Oh, this is the best part. This is one of those
wonderfully chaotic details of music history.
Unterberger notes that when Mick Jagger needed
the actual lyrics in the studio, he didn't use
Barry's version or Cole's version. He apparently
used a lyric sheet pulled from Perry Como's 1959
easy listening album Como Swings. Let's just
visualize that for a second. The Rolling Stones
are furiously trying to replicate Chuck Berry's
pioneering rock swagger, but Mick Jagger is standing
at the microphone reading from a Perry Como record.
It is a brilliant, messy game of musical telephone.
It really is. It shows how deeply embedded the
song was. It was everywhere. You could pull the
lyrics from a crooner and the riff from a rock
pint. in here and synthesize it into something
uniquely British. And speaking of the British
taking this Americana anthem and twisting it.
We have to talk about Billy Bragg. Yes. The Billy
Bragg adaptation is easily the wildest variation
in this entire deep dive because Bragg doesn't
just cover the song. He completely demolishes
the map. He threw out the map entirely. In 1985,
he goes into the BBC studios to record a legendary
John Peel radio session. These sessions were
famous for capturing raw alternative performances.
And Bragg debuts a completely anglicized version
of the track. He rips out the American geography.
Entirely. He retitles it A13, Trunk Wrote to
the Sea. The audacity of it is brilliant. He
keeps Bobby Troop's original 12 -bar blues progression
and that driving rhythm. But instead of romanticizing
the American Southwest, he replaces the lyrics
with towns along the A13 highway in England.
So instead of singing, get your kicks on Route
66. He's belting out, go motoring on the A13.
And instead of St. Louis or Oklahoma City, he's
charting a course through Wapping, Dagenham and
Grays. Which is just fantastic. The backstory
is that Bragg actually penned these localized
lyrics way back in 1977 when he was playing in
a punk band called Riff Raff. They had Route
66 in their set list, but Bragg just felt like
a total fraud singing about a sprawling American
highway he had never seen. He wanted authenticity.
Growing up in Barking, in East London, that drive
down the A13 toward the coastal town of South
End was his version of the open road. He even
described that specific route as feeling Springsteen
-ish. A working class escape route to a promised
land by the sea. If we connect this to the bigger
picture. What Billy Bragg did proves something
profound about Bobby Troop's original composition.
Troop didn't just write a song about U .S. geography.
He accidentally built a universal template for
the romanticism of the open road. Exactly. The
feeling of escape, of momentum, of rolling down
the windows and leaving your current reality
for something better just over the horizon. That
isn't strictly American. It's a fundamental human
urge. Whether you're in a Buick in the desert
or a beat -up Ford Escort heading to the Essex
Coast, the emotional resonance is identical.
Bragg just recognized the sturdy framework of
the song and bolted his own local map onto it.
though it took a while for people to actually
hear it. It's true. Bragg originally wanted A13
to be on his 1983 debut album, Life's a Riot
with Spy vs. Spy, but the legal red tape of getting
permission to alter the lyrics of Route 66 held
it up. That punk folk reimagining sat in the
vault for two decades. It finally got a commercial
release on his 2003 compilation, Must I Paint
You a Picture? The irony is that while Bragg
was waiting for clearance, Route 66 was busy
conquering entirely new sonic landscapes in the
1980s. In 1982, the vocal group, the Manhattan
Transfer, released a sophisticated, incredibly
complex vocal arrangement of the track. It charted
on the Hot 100. But more impressively, it won
a Grammy Award for Best Jazz Vocal Performance.
They even got it featured on the soundtrack for
the Burt Reynolds movie, Sharky's Machine. So
the song has mastered R &B, pop, rock and jazz
and then 1988 rolls around and the track takes
a hard pivot into the dark underground club scene
depeche mode yes a band known for their moody
industrial synthesizer sound releases a medley
combining route 66 with their own original track
behind the wheel this is where the 12 bar blues
foundation proves it is virtually indestructible
The contrast between Nat King Cole's acoustic
piano trio and Depeche Mode's cold metallic drum
machines and heavy synths is staggering. It sounds
like it shouldn't work. But because Troop's melody
is so fundamentally sound, you can strip away
all the organic instruments, dress the whole
thing up in black leather and electronic sequencing,
and it still functions perfectly as a driving,
hypnotic piece of music. It actually reached
number 61 on the Billboard Hot 100. It's wild.
And just to demonstrate that there was absolutely
no genre off limits, a couple of years later,
Michael Martin Murphy takes the song into the
heart of country music. He puts it on his 1989
album, Land of Enchantment. Releases it as a
single. in 1990 and it peaks at number 67 on
the billboard hot country singles chart which
makes perfect sense when you think about the
dna of country music the entire genre is built
on storytelling the imagery the traveler and
the working class journey murphy didn't even
need to radically alter the song to make it fit
he just leaned into the inherent twang and storytelling
that was already woven into the map based lyrics
which brings this unbelievable timeline all the
way into the 21st century because every new generation
eventually needs a road trip anthem. In 2006,
Pixar released the animated film Cars. Which
is a massive multi -million dollar love letter
to the real life fading towns along the actual
Route 66 highway. And naturally, the soundtrack
brings the song full circle. It honors the legacy
beautifully. The film actually features two distinctly
different renditions. They include the classic
Chuck Berry version from 1961. The very recording
that inspired the Rolling Stones and gave the
song its rock and roll teeth. And they also commissioned
a brand new, highly polished blues rock version.
by John Mayer. Mayer's guitar -heavy take wasn't
just tossed in for background ambiance either.
It earned him a Grammy nomination for Best Solo
Rock Vocal Performance. That is six decades after
Bobby and Cynthia Troup packed their bags in
Pennsylvania, and the song is still racking up
award nominations and reaching millions of kids
in movie theaters. So what does this all mean?
We started with a guy staring at a highway in
1946 trying to write a catchy tune to jumpstart
his Hollywood career. He writes a literal list
of cities from a paper map. And from that simple
list, we end up tracking a piece of music that
lived through Nat King Cole's swinging R &B,
Bing Crosby's pop, The Rolling Stones' chaotic
rock, Billy Bragg's Essex punk folk, Depeche
Mode's dark synths, Michael Martin Murphy's country
twang, and finally, a Pixar blockbuster. It is
an unmatched 60 -plus year sprint through modern
music history. It is a stunning trajectory. And
I think for you listening today, there's a...
Profound practical takeaway here about the nature
of creating something that lasts. Bobby Troup
didn't try to reinvent the wheel. Right. He took
an incredibly relatable human experience, the
optimism of a road trip, and he gave it a clear
logical structure. He literally used a map to
give it direction. And he used a foundational
12 -bar blues progression to give it rhythm.
He built a solid house. He built a house with
a perfect foundation. And because that framework
was so sturdy, the song could be endlessly remodeled.
It's a great reminder that you don't always need
to create something utterly incomprehensible
or wildly avant -garde to leave a mark. Sometimes
you just need a sturdy foundation, a good framework,
and the willingness to let others bring their
own unique perspectives to it. The Stones brought
their aggressive swagger, Depeche Mode brought
their industrial edge, and Bragg brought his
local working class pride. The song accommodated
all of them because the core was so strong. It
is the ultimate blank canvas. As long as you
keep moving forward, the song works. But this
raises an important question. Let's think back
to Bobby Troop sitting at that desk in Los Angeles
looking closely at his map and completely forgetting
to include Albuquerque in his lyrics. Right.
He mapped out his westward journey perfectly
step by step, but he accidentally left out a
massive, unmissable milestone right in the middle.
Just skipped right over it. If you were to sit
down today and map out a song or a story about
your own daily life or your own career journey
from where you started to where you are now.
What Albuquerque would you suddenly realize you
left out because you were so hyper -focused on
the final destination? It's definitely something
to think about the next time you're out on the
road.