WEBVTT

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I want you to picture something for a second.

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Imagine you are standing in a driveway in Pennsylvania.

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Okay. It's early 1946. The world is just starting

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to exhale after the Second World War. Exactly.

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And you're packing the trunk of a 1941 Buick.

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You're loading up suitcases, double -checking

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the tires, and staring at this massive paper

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map that stretches all the way to the sunny coast

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of California. You're chasing a massive dream.

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You really are, specifically making it big as

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a songwriter in Hollywood. So you turn the key,

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you hit the road, and you are completely, blissfully

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unaware that before you even reach the Pacific

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Ocean, you are going to write a piece of absolute

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music history. Which is wild to think about.

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Welcome to the Deep Dive. We are jumping into

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a story today that is going to completely alter

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the way you hear a legendary piece of Americana.

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It really is the quintessential American road

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trip narrative. What we're doing today is sorting

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through a massive encyclopedic breakdown of the

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1946 Rhythm and Blues classic, Get Your Kicks

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on Route 66. Oh, yeah. And the documentation

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we have covers everything, you know. Its highly

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spontaneous origins, its immediate and enduring

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chart -topping history, and its incredibly strange

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cultural footprint that spans across oceans and

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generations. The mission for today is to trace

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how a very simple map inspired tune became the

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ultimate musical chameleon. Looking at a standard

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that effortlessly jumped from its R &B roots

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right into pop, rock, jazz, country. And even

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British punk adjacent folk. Yes. OK, let's unpack

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this. We have to go back to that 1941 Buick and

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see what was actually happening in the passenger

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cabin. Right. So behind the wheel is Bobby Troop.

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He's an American songwriter and he's taking this

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massive 10 day cross -country relocation. with

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his wife, Cynthia. A 10 -day drive. Yeah, and

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anyone who has ever done a multi -day drive knows

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the highway hypnosis sets in quickly. Oh, definitely.

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Your mind starts scanning for anything to focus

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on. And for a songwriter like Troop, the road

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itself became the canvas. But the funny thing

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is, his initial idea wasn't even about Route

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66. No, it wasn't. He was driving west and thought,

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I should write a raid song about U .S. Highway

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40. Which, U .S. 40 was a major artery, but is

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a lyric. It's incredibly clunky. Yeah, it lacks

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that rhythmic punch. It really does. And that

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is the exact moment Cynthia Troop steps in and

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alters music history because they eventually

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transition off US 40 and merge onto US Highway

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66. The famous stretch from Chicago down to L

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.A. Right. And Cynthia turns to him and casually

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pitches the title, Get Your Kicks on Route 66.

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She handed him the definitive hook of his career.

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Yeah. I mean, it's got that sharp. percussive

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consonants, the kicks, 66. It's perfect. But

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the timeline of the actual songwriting process

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is what really stands out in the documentation.

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Troup gets this title from his wife and starts

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working out the melody and the concept during

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the 10 -day drive. Literally writing it while

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the tires are rolling over the asphalt. Exactly.

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But he couldn't actually finish the lyrics from

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memory. Wait, he drove the entire route and still

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couldn't remember the towns in order? Not well

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enough to write a cohesive song. It wasn't until

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they finally parked in Los Angeles that he was

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able to sit down at a desk, unfold a physical

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paper map of the very highway he had just traversed,

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and manually construct the lyrics by listing

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the cities and towns along the way. That is hilarious.

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He needed an atlas to finish his own diary entry.

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Basically, yeah. And the best part is that even

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with the map sitting right in front of him, tracing

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the route with his finger, he makes a massive

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geographical blunder. A huge omission. Cynthia

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later pointed out her utter disbelief that he

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managed to write a song cataloging their trip

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and completely left out Albuquerque. He just

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sailed right past it. One of the biggest cities

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in New Mexico. What's fascinating here is how

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that highly specific list -based lyric style

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actually functions for the listener. Right. By

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meticulously or almost meticulously minus Albuquerque.

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Right. Minus Albuquerque. Naming these waypoints

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like St. Louis, Joplin, Oklahoma City and Amarillo,

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Troup isn't just writing a vague ode to travel.

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He is handing the listener a tangible itinerary.

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It grounds the song. You feel like you are sitting

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in the backseat of that Buick watching the road

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signs blur past. Exactly. So Troop is in Los

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Angeles. He's got these map assisted lyrics and

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he pitches it. And the song lands in the hands

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of an absolute titan. Nat King Cole. On March

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16th, 1946, Nat King Cole and the King Cole trio

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walk into radio recorders in Los Angeles and

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lay down the very first studio recording. And

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Capitol Records puts it out. The context of that

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release. tells you a lot about the musical landscape.

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Yeah, the B -side is interesting. Right, the

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B -side to this single was a track called Everyone

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Is Saying Hello Again, Why Must We Say Goodbye?

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Which is a classic, sentimental 1940s ballad.

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Very standard for the era. But flip that record

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over, and the A -side, Route 66, is a completely

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different beast. It explodes. It immediately

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hits number three on the race records chart.

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Which we now know as the R &B charts. Yes, and

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it climbs to number 11 on the broader pop singles

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chart. Nat King Cole loved the track so much

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that he made it a permanent fixture of his career.

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He re -recorded it a few times, didn't he? He

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did. Once for his 1956 album, After Midnight,

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and again for the Nat King Cole story in 1961.

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And we really need to pause and examine why Nat

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King Cole's original arrangement. became the

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bedrock for everything that followed let's do

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it if you listen to that 1946 recording it is

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built on a very standard 12 bar blues progression

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musically speaking that is one of the sturdiest

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most universally understood frameworks in Western

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music. It's the architectural equivalent of a

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steel frame building. You know it's not going

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to fall over. Precisely. The King Cole trio took

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that 12 -bar blues structure and injected it

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with this incredibly tight, swinging, upbeat

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rhythm. The interplay between the piano and the

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guitar. It's light but driving. It mimics the

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momentum of a car cruising down the highway.

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By establishing it as this infectious rhythm

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and blues standard right out of the gate, Cole

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proved the song's structural integrity. Because

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it was mathematically simple enough. Exactly.

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You could speed it up, slow it down, or completely

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change the instrumentation without losing the

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song's core identity. Here's where it gets really

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interesting. Because the moment a song proves

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it has that kind of bulletproof structure, every

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other artist wants to take it for a test drive.

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They want their own spin on it. The genre hopping

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begins almost instantaneously. In that very same

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year, 1946, Bing Crosby teams up with the Andrews

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sisters and drops their own version. And they

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take it to number 14 on the Billboard chart.

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So in its birth year, you have the pioneering,

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swinging R &B of Nat King Cole and the heavily

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orchestrated, tight commercial pop harmonies

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of the Andrews sisters, both charting simultaneously.

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It's the first proof of the chameleon effect.

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And the song just keeps absorbing the cultural

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shifts around it. When the rhythm and blues era

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gives way to the rock and roll revolution. 1966

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doesn't get left behind it gets weaponized fast

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forward to 1964 the British invasion is in full

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swing And a young band called the Rolling Stones

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decides Route 66 needs to be on their self -titled

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debut album. The music critic Richie Unterberger

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has a great piece of analysis on this. He calls

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the Stones take the most famous rock version

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of the song. Because it wasn't just album filler.

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No, it was the centerpiece of their early live

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tours. They were cutting their teeth on this

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American road anthem. They even released a live

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version on their 1965 UK EP Got Live, if you

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want it. And the U .S. The sonic shift from Nat

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King Cole's smooth piano trio to Keith Richards'

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gritty, overdriven guitar is massive. Completely

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different vibe. But the craziest part of the

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Stones' version is the actual lineage of how

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they put it together. They weren't trying to

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channel Nat King Cole at all. No, they were channeling

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Chuck Berry. Berry had recorded a phenomenal

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guitar -heavy version for his 1961 album, New

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Jukebox Hits. And the Stones worshipped Chuck

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Berry. They adopted his raw, aggressive rhythm.

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Oh, this is the best part. This is one of those

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wonderfully chaotic details of music history.

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Unterberger notes that when Mick Jagger needed

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the actual lyrics in the studio, he didn't use

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Barry's version or Cole's version. He apparently

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used a lyric sheet pulled from Perry Como's 1959

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easy listening album Como Swings. Let's just

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visualize that for a second. The Rolling Stones

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are furiously trying to replicate Chuck Berry's

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pioneering rock swagger, but Mick Jagger is standing

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at the microphone reading from a Perry Como record.

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It is a brilliant, messy game of musical telephone.

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It really is. It shows how deeply embedded the

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song was. It was everywhere. You could pull the

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lyrics from a crooner and the riff from a rock

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pint. in here and synthesize it into something

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uniquely British. And speaking of the British

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taking this Americana anthem and twisting it.

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We have to talk about Billy Bragg. Yes. The Billy

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Bragg adaptation is easily the wildest variation

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in this entire deep dive because Bragg doesn't

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just cover the song. He completely demolishes

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the map. He threw out the map entirely. In 1985,

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he goes into the BBC studios to record a legendary

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John Peel radio session. These sessions were

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famous for capturing raw alternative performances.

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And Bragg debuts a completely anglicized version

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of the track. He rips out the American geography.

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Entirely. He retitles it A13, Trunk Wrote to

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the Sea. The audacity of it is brilliant. He

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keeps Bobby Troop's original 12 -bar blues progression

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and that driving rhythm. But instead of romanticizing

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the American Southwest, he replaces the lyrics

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with towns along the A13 highway in England.

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So instead of singing, get your kicks on Route

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66. He's belting out, go motoring on the A13.

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And instead of St. Louis or Oklahoma City, he's

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charting a course through Wapping, Dagenham and

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Grays. Which is just fantastic. The backstory

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is that Bragg actually penned these localized

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lyrics way back in 1977 when he was playing in

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a punk band called Riff Raff. They had Route

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66 in their set list, but Bragg just felt like

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a total fraud singing about a sprawling American

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highway he had never seen. He wanted authenticity.

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Growing up in Barking, in East London, that drive

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down the A13 toward the coastal town of South

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End was his version of the open road. He even

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described that specific route as feeling Springsteen

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-ish. A working class escape route to a promised

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land by the sea. If we connect this to the bigger

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picture. What Billy Bragg did proves something

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profound about Bobby Troop's original composition.

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Troop didn't just write a song about U .S. geography.

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He accidentally built a universal template for

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the romanticism of the open road. Exactly. The

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feeling of escape, of momentum, of rolling down

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the windows and leaving your current reality

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for something better just over the horizon. That

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isn't strictly American. It's a fundamental human

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urge. Whether you're in a Buick in the desert

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or a beat -up Ford Escort heading to the Essex

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Coast, the emotional resonance is identical.

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Bragg just recognized the sturdy framework of

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the song and bolted his own local map onto it.

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though it took a while for people to actually

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hear it. It's true. Bragg originally wanted A13

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to be on his 1983 debut album, Life's a Riot

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with Spy vs. Spy, but the legal red tape of getting

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permission to alter the lyrics of Route 66 held

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it up. That punk folk reimagining sat in the

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vault for two decades. It finally got a commercial

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release on his 2003 compilation, Must I Paint

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You a Picture? The irony is that while Bragg

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was waiting for clearance, Route 66 was busy

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conquering entirely new sonic landscapes in the

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1980s. In 1982, the vocal group, the Manhattan

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Transfer, released a sophisticated, incredibly

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complex vocal arrangement of the track. It charted

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on the Hot 100. But more impressively, it won

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a Grammy Award for Best Jazz Vocal Performance.

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They even got it featured on the soundtrack for

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the Burt Reynolds movie, Sharky's Machine. So

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the song has mastered R &B, pop, rock and jazz

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and then 1988 rolls around and the track takes

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a hard pivot into the dark underground club scene

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depeche mode yes a band known for their moody

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industrial synthesizer sound releases a medley

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combining route 66 with their own original track

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behind the wheel this is where the 12 bar blues

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foundation proves it is virtually indestructible

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The contrast between Nat King Cole's acoustic

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piano trio and Depeche Mode's cold metallic drum

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machines and heavy synths is staggering. It sounds

00:12:27.480 --> 00:12:29.799
like it shouldn't work. But because Troop's melody

00:12:29.799 --> 00:12:32.700
is so fundamentally sound, you can strip away

00:12:32.700 --> 00:12:34.940
all the organic instruments, dress the whole

00:12:34.940 --> 00:12:37.039
thing up in black leather and electronic sequencing,

00:12:37.299 --> 00:12:40.720
and it still functions perfectly as a driving,

00:12:40.820 --> 00:12:43.200
hypnotic piece of music. It actually reached

00:12:43.200 --> 00:12:46.250
number 61 on the Billboard Hot 100. It's wild.

00:12:46.389 --> 00:12:48.450
And just to demonstrate that there was absolutely

00:12:48.450 --> 00:12:51.409
no genre off limits, a couple of years later,

00:12:51.529 --> 00:12:54.169
Michael Martin Murphy takes the song into the

00:12:54.169 --> 00:12:57.090
heart of country music. He puts it on his 1989

00:12:57.090 --> 00:13:00.269
album, Land of Enchantment. Releases it as a

00:13:00.269 --> 00:13:04.299
single. in 1990 and it peaks at number 67 on

00:13:04.299 --> 00:13:06.240
the billboard hot country singles chart which

00:13:06.240 --> 00:13:08.039
makes perfect sense when you think about the

00:13:08.039 --> 00:13:11.000
dna of country music the entire genre is built

00:13:11.000 --> 00:13:14.039
on storytelling the imagery the traveler and

00:13:14.039 --> 00:13:16.080
the working class journey murphy didn't even

00:13:16.080 --> 00:13:18.679
need to radically alter the song to make it fit

00:13:18.679 --> 00:13:21.840
he just leaned into the inherent twang and storytelling

00:13:21.840 --> 00:13:24.759
that was already woven into the map based lyrics

00:13:24.759 --> 00:13:27.559
which brings this unbelievable timeline all the

00:13:27.559 --> 00:13:30.200
way into the 21st century because every new generation

00:13:30.250 --> 00:13:33.070
eventually needs a road trip anthem. In 2006,

00:13:33.389 --> 00:13:36.200
Pixar released the animated film Cars. Which

00:13:36.200 --> 00:13:39.200
is a massive multi -million dollar love letter

00:13:39.200 --> 00:13:42.259
to the real life fading towns along the actual

00:13:42.259 --> 00:13:45.019
Route 66 highway. And naturally, the soundtrack

00:13:45.019 --> 00:13:47.659
brings the song full circle. It honors the legacy

00:13:47.659 --> 00:13:51.539
beautifully. The film actually features two distinctly

00:13:51.539 --> 00:13:53.519
different renditions. They include the classic

00:13:53.519 --> 00:13:56.740
Chuck Berry version from 1961. The very recording

00:13:56.740 --> 00:13:59.220
that inspired the Rolling Stones and gave the

00:13:59.220 --> 00:14:01.519
song its rock and roll teeth. And they also commissioned

00:14:01.519 --> 00:14:05.000
a brand new, highly polished blues rock version.

00:14:05.340 --> 00:14:08.179
by John Mayer. Mayer's guitar -heavy take wasn't

00:14:08.179 --> 00:14:10.179
just tossed in for background ambiance either.

00:14:10.340 --> 00:14:13.039
It earned him a Grammy nomination for Best Solo

00:14:13.039 --> 00:14:16.220
Rock Vocal Performance. That is six decades after

00:14:16.220 --> 00:14:18.519
Bobby and Cynthia Troup packed their bags in

00:14:18.519 --> 00:14:21.120
Pennsylvania, and the song is still racking up

00:14:21.120 --> 00:14:23.379
award nominations and reaching millions of kids

00:14:23.379 --> 00:14:25.440
in movie theaters. So what does this all mean?

00:14:25.600 --> 00:14:27.820
We started with a guy staring at a highway in

00:14:27.820 --> 00:14:30.559
1946 trying to write a catchy tune to jumpstart

00:14:30.559 --> 00:14:32.980
his Hollywood career. He writes a literal list

00:14:32.980 --> 00:14:35.600
of cities from a paper map. And from that simple

00:14:35.600 --> 00:14:37.679
list, we end up tracking a piece of music that

00:14:37.679 --> 00:14:40.159
lived through Nat King Cole's swinging R &B,

00:14:40.419 --> 00:14:43.519
Bing Crosby's pop, The Rolling Stones' chaotic

00:14:43.519 --> 00:14:47.059
rock, Billy Bragg's Essex punk folk, Depeche

00:14:47.059 --> 00:14:50.179
Mode's dark synths, Michael Martin Murphy's country

00:14:50.179 --> 00:14:53.879
twang, and finally, a Pixar blockbuster. It is

00:14:53.879 --> 00:14:57.659
an unmatched 60 -plus year sprint through modern

00:14:57.659 --> 00:15:00.779
music history. It is a stunning trajectory. And

00:15:00.779 --> 00:15:02.679
I think for you listening today, there's a...

00:15:03.679 --> 00:15:06.679
Profound practical takeaway here about the nature

00:15:06.679 --> 00:15:09.980
of creating something that lasts. Bobby Troup

00:15:09.980 --> 00:15:12.559
didn't try to reinvent the wheel. Right. He took

00:15:12.559 --> 00:15:15.200
an incredibly relatable human experience, the

00:15:15.200 --> 00:15:17.600
optimism of a road trip, and he gave it a clear

00:15:17.600 --> 00:15:20.019
logical structure. He literally used a map to

00:15:20.019 --> 00:15:22.019
give it direction. And he used a foundational

00:15:22.019 --> 00:15:24.580
12 -bar blues progression to give it rhythm.

00:15:24.700 --> 00:15:26.899
He built a solid house. He built a house with

00:15:26.899 --> 00:15:29.220
a perfect foundation. And because that framework

00:15:29.220 --> 00:15:32.000
was so sturdy, the song could be endlessly remodeled.

00:15:32.269 --> 00:15:33.789
It's a great reminder that you don't always need

00:15:33.789 --> 00:15:35.929
to create something utterly incomprehensible

00:15:35.929 --> 00:15:39.129
or wildly avant -garde to leave a mark. Sometimes

00:15:39.129 --> 00:15:42.610
you just need a sturdy foundation, a good framework,

00:15:42.830 --> 00:15:45.129
and the willingness to let others bring their

00:15:45.129 --> 00:15:47.509
own unique perspectives to it. The Stones brought

00:15:47.509 --> 00:15:50.090
their aggressive swagger, Depeche Mode brought

00:15:50.090 --> 00:15:53.169
their industrial edge, and Bragg brought his

00:15:53.169 --> 00:15:56.559
local working class pride. The song accommodated

00:15:56.559 --> 00:15:58.879
all of them because the core was so strong. It

00:15:58.879 --> 00:16:02.159
is the ultimate blank canvas. As long as you

00:16:02.159 --> 00:16:05.500
keep moving forward, the song works. But this

00:16:05.500 --> 00:16:08.240
raises an important question. Let's think back

00:16:08.240 --> 00:16:10.879
to Bobby Troop sitting at that desk in Los Angeles

00:16:10.879 --> 00:16:13.639
looking closely at his map and completely forgetting

00:16:13.639 --> 00:16:15.899
to include Albuquerque in his lyrics. Right.

00:16:16.019 --> 00:16:18.200
He mapped out his westward journey perfectly

00:16:18.200 --> 00:16:21.320
step by step, but he accidentally left out a

00:16:21.320 --> 00:16:24.159
massive, unmissable milestone right in the middle.

00:16:24.240 --> 00:16:26.379
Just skipped right over it. If you were to sit

00:16:26.379 --> 00:16:29.460
down today and map out a song or a story about

00:16:29.460 --> 00:16:31.899
your own daily life or your own career journey

00:16:31.899 --> 00:16:33.659
from where you started to where you are now.

00:16:34.679 --> 00:16:36.879
What Albuquerque would you suddenly realize you

00:16:36.879 --> 00:16:39.279
left out because you were so hyper -focused on

00:16:39.279 --> 00:16:41.679
the final destination? It's definitely something

00:16:41.679 --> 00:16:43.399
to think about the next time you're out on the

00:16:43.399 --> 00:16:43.620
road.