3 Songs That Made Me Understand These Iconic 20th-Century Artists on a Deeper Level

It only takes one song to turn you on to an artist. That’s the whole concept behind the “big break.” One hit can completely change someone’s life. Moreover, this kind of instant connection can happen to already established artists. Listeners encounter legends in different ways and at different times. The three songs below helped me to “get” three iconic musicians.

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“The Great Compromise” — John Prine

John Prine has long been an artist I’ve frequented, but prior to hearing “The Great Compromise,” I didn’t truly understand what the Americana icon was getting at. Sure, his tongue-in-cheek yet strikingly honest lyricism always had an impact, but his worldview didn’t take shape until I uncovered this ballad.

Prine has many songs that speak to the world around us, politics, and social issues, but none are as striking as this one. “The Great Compromise” sees Prine lay bare his view on America post-Vietnam. For an artist in the country/roots space, this was a bold opinion. He delivered his hard-earned perspective in a way only he could: with a humor capable of lightening the load.

“To Ramona” — Bob Dylan

Similarly, I’ve always recognized the era-defining genius of Bob Dylan, but it never fully hit me until I heard “To Ramona.” Dylan uses his sprawling lyricism here, giving the song’s subject (and the listener by proxy) some well-needed advice.

“I’ve heard you say many times / That you’re better than no one / And no one is better than you / If you really believe that / You know you have / Nothing to win and nothing to lose,” the lyrics read. Dylan penned this song for Joan Baez, but it has universal applications. This is the song that turned me from a Dylan appreciator to a full-blown fan.

“Hey, That’s No Way To Say Goodbye” — Leonard Cohen

Leonard Cohen has never really been an artist that I felt particularly strong about. I knew his biggest hits and understood his appeal, but his complex and deeply emotive songwriting wasn’t something I turned to often. That is, until I heard “Hey, That’s No Way To Say Goodbye.”

This simple love song is one of the tenderest I’ve ever heard. “Walk me to the corner, our steps will always rhyme / You know my love goes with you as your love stays with me / It’s just the way it changes, like the shoreline and the sea,” the lyrics read. Deeply poetic and relatable to any pair of lovers, this song has a universality that I hadn’t recognized in Cohen until I heard it.

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