How Willie Nelson Went Against the Nashville Grain To Score His First-Ever US Pop Hit

Some artists are pretty adept at giving audiences just what they want time and again. Then there are those with a knack for delivering something that music fans didn’t realize that they needed to hear.

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Willie Nelson, following his outlaw tendencies, did just that in 1975. He walked away with a massive country hit and his first-ever pop crossover success by going way against the grain.

Willie’s Way

Willie Nelson became a kind of warm, avuncular presence in the 80s. He even made his impact on the pop charts with some sweet ballads now and again. But his first journey into that rarefied air came as a result of him forging his own path, much to the consternation of the music industry powers-that-be.

Nelson found his first taste of success in the early 60s as an ace songwriter, penning massive hits like “Hello Walls” and “Crazy” for others. He eventually grabbed the opportunity to be an artist in his own right in that decade, where he established himself as a reliable hitmaker, if not a superstar.

As the 70s dawned, Nelson began to chafe at the expectations of the Nashville establishment that ruled the country music roost. He disliked the lush orchestration constantly ladled on his recordings. And he longed to try different things that usually weren’t done in the country genre, such as concept albums.

‘Stranger’ Days

Nelson started to find his footing when he recorded the albums Shotgun Willie (1973) and Phases And Stages (1974). The latter was a concept record, and each of the albums found Nelson going a bit adrift from the topics and song structures found in typical country songs of the era.

The next step was complete recording autonomy, which he received upon signing with Columbia Records. Nelson worked out an unshakeable contract by which he controlled what went on his records without fail. That set the stage for the album Red Headed Stranger in 1975.

Nelson had always been fond of the 50s song “Tale Of The Red Headed Stranger”. Only he imagined a much larger narrative behind the song, one that he could tease out over the entirety of an album. He did this with both original songs and carefully chosen covers. “Blue Eyes Crying In The Rain” was one of the latter and was chosen as the lead single off the album Red Headed Stranger.

The “Rain” Song

Fred Rose wrote “Blue Eyes Crying In The Rain”. The first recording of it came all the way back in 1947. Country legends like Roy Acuff, Hank Williams, and Conway Twitty all recorded it. Nelson heard it as a perfect evocation of the album protagonist’s sorrow.

Like much of Red Headed Stranger, “Blue Eyes Crying In The Rain” came adorned with only the sparsest of instrumentation, Nelson’s woebegone vocal taking center stage. Columbia execs allegedly flipped when they heard the album, believing Nelson had essentially delivered them a glorified demo.

Yet “Blue Eyes Crying In The Rain” turned into a country chart-topper and made it to No. 21 on the pop charts, the first time Nelson accomplished either feat. And it acted as the emotional centerpiece for one of the most influential country albums in history.

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