1. "On the Road Again" by Willie Nelson. Willie Nelson's iconic country-pop crossover "On the Road Again" is a genuine road trip anthem. The 1980 tune was named by Rolling Stone magazine as one of the "500 Greatest Songs of All Time." Also honored as a Grammy Hall of Fame song, it is about life on tour with a band of music-making buddies who are best friends.. The Long and Winding Road - The Beatles. This song was written amid The Beatles' breakup. Full of tension, regret, and reflection, this song talks about the steadiness of a path back to your roots. No matter where you go, what you face, or how you change, "the long and winding road that leads to your door will never disappear.".

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2. "Goodbye Yellow Brick Road" By Elton John. One of the most popular hits about roads is Elton John 's "Goodbye Yellow Brick Road.". The titular road here was inspired by the movie The Wizard of Oz, where Dorothy and company traverse the yellow brick road. In the song, the yellow brick road is a metaphor for opulence.. Songs With "Road" in the Title. These are the most popular songs whose titles contain the word "Road." RANK SONG TITLE ARTIST(S) YEAR; 1: The Long and Winding Road: The Beatles: 1969: 2: Roadhouse Blues: The Doors: 1970: 3: Hit the Road, Jack: Ray Charles: 1961: 4: Goodbye Yellow Brick Road: Elton John: 1973: 5: