While he is hailed today as one of the iconic musicians of his time, there was a time when Willie Nelson was trying to sell his songs for meal money like a fruit vendor on the streets.

Such was the case when he arrived in Nashville, Tennessee in 1960, a broke balladeer armed with a trove of songs that would eventually become hits for other artists, including a yearning ballad for a lost lover that was originally called "Stupid," before getting retitled as "Crazy."

At the time, country singer Patsy Cline was enduring her own professional and personal difficulties, her momentum stalled since her 1957 breakthrough with "Walkin' After Midnight." In June 1961, as she was finally making headway with a much-needed follow-up hit, "I Fall to Pieces," she was in a horrific car accident that left her hospitalized in critical condition.

Nelson brought a demo to Cline's home but wouldn't go inside

Things were soon looking up for both artists. "I Fall to Pieces" reached the top spot on the country charts while Cline was recuperating, and word was out around Nashville's music community that she was ready to make another splash. Meanwhile, Nelson had scored a gig with Pamper Music, his reputation as a gifted, albeit unorthodox, songwriter gaining steam thanks to his recent successes for Faron Young ("These Walls") and Billy Walker ("Funny How Time Slips Away").

There are differing accounts of how "Crazy" wound up with the chanteuse who delivered its definitive version. According to Willie Nelson: An Epic Life, Cline's husband and manager, Charlie Dick, had irritated his wife by playing a Nelson song over and over, leaving a bad taste in her mouth when the songwriter's name was mentioned. As a result, when Nelson and fellow Pamper Music scribe Hank Cochran arrived a few days later with a demo of "Crazy," Nelson hid in the car until Cline went out to retrieve "that little son of a b***h" herself.

‌In the alternate version relayed in It's a Long Story: My Life, Nelson claimed he played the "Crazy" demo for Dick at the local hangout, after which Dick insisted on immediately bringing it home for his wife to hear. Because it was after 1 a.m., Nelson was hesitant to go inside, until Cline, a hospitable "sweetheart," came to get him.

Cline's reaction to "Crazy" is also disputed. Nelson recalled her saying she was "glad" he wrote the song and planned to record it, while other sources say she had her eye on different material and was loath to take on an aching heartbreaker of this type.

READ MORE: Inside Patsy Cline and Loretta Lynn's Instantaneous and Unbreakable Bond

Cline nailed her recording performance in one take

Regardless, "Crazy" was placed on Cline's recording schedule at producer Owen Bradley's Quonset Hut Studio. Recognizing the potential in this piece of music, Bradley whipped up a lavish arrangement, focusing on instruments like the drums, electric guitar and piano, unusual for country music at the time. He also pulled in the Jordanaires, a quartet that found fame backing Elvis Presley, for an extra layer of harmonies.

The lead vocals were another story. Nelson's demo, which featured his idiosyncratic sense of meter and phrasing, left everyone flummoxed as they tried to mold it into a number befitting Cline's style. Furthermore, the singer was still in pain and unable to belt out certain notes with her customary vigor. After temporarily shelving her input, Cline returned to the studio a few days later and nailed her performance, with its melodic leaps and dramatic pauses, in one take.

There was one more obstacle to "Crazy" reaching the masses: Billy Walker, who valued Nelson after the success of "Funny How Time Slips Away," had a "hold" on the song that gave him first rights to its release. That was quickly rectified, however, when Cochran promised to provide another hit song in its place.

"Crazy" became one of the biggest jukebox hits of all time

Released in October 1961 by Decca Records, "Crazy" became a No. 2 country hit and rose to No. 9 on the Hot 100, though its chart performance only tells a small part of its legacy. It became one of Cline's signature songs, the torch of a life cut short by a plane crash a year and a half later, as well as a standard covered by the likes of Loretta Lynn, Linda Ronstadt and LeAnne Rhimes, among others. In 1988, as part of celebrations for the 100th-year anniversary of the jukebox, the Amusement and Music Operators Association named "Crazy" and Presley's "Hound Dog" as the most-played jukebox hits of all time.

All it took were the combined powers of two legendary artists, one an out-of-the-box songwriter and the other a perfectionist, powerhouse singer, who were crazy enough to tap into the universal longing that made this song a classic for the ages.