Willie Nelson’s songs had always been a big part of the country music scene. He has established himself as the most ‘unique and versatile country artist of all time’ as Rolling Stones described him in their article for the legend’s 85th. He is that country swooner with jazz phrasing showing off his guitar licks on his signature beat-up classical guitar that his fans know all too well.
In his decades-long career, Willie Nelson successfully showcased his talent in writing hits not only for himself but for other country music artists as well. He was also no slave to any style and pretty much did anything he wanted. He explored hard-core country, western swing, gospel, folk, jazz, and many more. He also collaborated with many great music artists and covered many different songs that definitely made an impact.
To say it’s difficult to pick the best 10 best Willie Nelson songs would be an understatement. In this list, we featured a bit of everything that represents the American music icon. These songs definitely deserve a listen, even at this age.
1. Crazy, 1961
Crazy was a ballad penned by Willie Nelson himself when he was still a struggling songwriter back then. According to sources, Nelson pitched the song to Patsy Cline’s husband in Nashville’s Tootsie’s Orchid Lounge which turned out to be Patsy Cline’s career-changing hit in 1962.
Patsy Cline released the song as a follow-up to another previous hit, I Fall to Pieces, in late 1961. It immediately became a huge hit peaking at number 2 in the country hits. Aside from being a jukebox and karaoke favorite, the song also easily became one of her signature tunes. Her version amongst many became the most notable one earning the 85th spot on Rolling Stone’s The 500 Greatest Songs of All Time, the third highest-ranking song by a solo female artist.
This also propelled Nelson’s songwriting prowess. His own version appeared on his 1962 debut album …And Then I Wrote.
2. Half a Man, 1963
Up to this point, Willie Nelson was still struggling to make his own name in the industry despite being one of the go-to composers in Nashville thanks to many of his chart-topping hits like the above mentioned Patsy Cline’s Crazy, Faron Young’s Hello Walls, and Ray Price’s Night Life.
Half a Man was inspired by a moment wherein Nelson woke up in the middle of the night to smoke, but his arm was around a sleeping woman. He couldn’t release his arm without waking her. And that was how he told a story of a man who said that if he lost a part of his body, he would be half a man which a lost love turned him into.
Half a Man made considerable chart success reaching number 25 on Billboard’s Hot Country Singles and also number 20 on Cashbox’s country singles. In 1982, another legend Merle Haggard covered the song for his album Going Where the Lonely Go. And then in 1985, Nelson recorded a duet of the song with George Jones for his album Half Nelson.
3. Whiskey River, 1973
This song was originally co-written by Texas country singer Johnny Bush alongside composer Paul Stroud for his 1972 album of the same name. The song peaked at number 14 on the country charts.
A year later, Willie Nelson, who is also Bush’s good friend, covered the song for his 1973 album Shotgun Willie. But it was only in 1978 that the cover was released as a single in the live album Willie and Family Live, which also earned attention and praises. The song peaked at number 12 on the country chart and also earned Nelson a Grammy nomination for Best Country Vocal Performance (Male). Despite not being an original Nelson song, it became one of his signature songs and also a staple opener for his concerts.
4. Blue Eyes Crying in the Rain, 1975
Before this song, Willie Nelson was more popularly known as a songwriter rather than a performer. But with the release of the song as part of his 1975 album Red Headed Stranger, Nelson earned his first number 1 hit as a singer. Blue Eyes Crying in the Rain became so big that it also reached number 21 on the Billboard Hot 100 and was named the 3rd biggest song of 1975 on the Billboard Hot Country Singles chart.
The song was originally released in the ‘40s, written by songwriter Fred Rose and originally performed by Roy Acuff. It was also covered by various artists, but Nelson’s cover was undeniably the most iconic.
5. Georgia On My Mind, 1978
When people mention this 1930 song, it’s commonly more associated with American musician Ray Charles who recorded the song for his 1960 album Genius Hits the Road. And in 1979, the State of Georgia even designated Ray Charles’ version as the official state song.
The song, which was originally penned by Hoagy Carmichael and Stuart Gorrell and first officially recorded by Hoagy Carmichael in 1930, was also covered by Willie Nelson. Nelson recorded it for his 1978 album Stardust and the song hit number one on the country charts making it his third solo number one.
6. My Heroes Have Always Been Cowboys, 1980
This song was written by Sharon Vaughn and was first recorded by Waylon Jennings for his 1976 album Wanted! The Outlaws. And like many other cover songs immortalized by Willie Nelson, this song was no exception. The song was his debut single from his The Electric Horseman album, which also served as a soundtrack to the film of the same name starred by Robert Redford and Jane Fonda, where he also appeared.
The song became his fifth number one on the country chart and was also chosen as one of the Top 100 Western songs of all time by the Western Writers of America. In 1992, it was also named as one of the Top 100 Country Songs of All Time.
7. Angel Flying Too Close to the Ground, 1980
Angel Flying Too Close to the Ground was a song written and performed by Willie Nelson as part of his film Honeysuckle Rose soundtrack. The film was his first leading role in a major motion picture, and he was already 47 at the time. The song was released in January 1981 as the second single of the soundtrack and earned Nelson his seventh number one on the country charts.
Aside from commercial success, the song also hit close to home as he would often dedicate it to his son Billy Nelson who died from suicide in 1991 during his live performances. Bob Dylan also covered the song for his 1983 album Infidels, while Alison Krauss recorded a cover for her 2017 release Windy City.
8. On The Road Again, 1980
On the Road Again song was also part of his film Honeysuckle Rose’s soundtrack. While the film was not a great success, the songs received a better reception. This song which was originally written by Willie Nelson on an airsickness bag on the plane, earned him another country hit and also one of his biggest crossovers at that time. Not to mention that it also bagged him a Grammy for Best Country Song.
In 2004, it also ranked on the 500 Greatest Songs of All Time by the Rolling Stone. And in 2011, it was inducted into the Grammy Hall of Fame.
9. Always on My Mind, 1982
This song was considered Willie Nelson’s biggest hit as an artist that he did not write. Always on My Mind was a ballad song originally penned by Wayne Carson, Johnny Christopher, and Mark James. It had been a crossover hit in country, western, and pop categories with over 300 recorded releases. His was definitely one of the most iconic versions ranking at number 5 on Billboard’s Hot 100 and also earning Nelson another number one hit.
According to his 1988 autobiography, Willie really bowled over the moment he heard the song. It was one of the beautiful, sad songs with haunting melodies that you couldn’t get out of your mind, and the lyrics really stuck with him. In 1982, the Country Music Association named it Single of the Year and it also earned Nelson 3 Grammy Awards, including Song of the Year, Best Male Country Vocal Performance, and Best Country Song.
10. Pancho & Lefty, 1983
Of course, we couldn’t leave out the collaboration between Willie Nelson and Merle Haggard in the list. The Pancho & Lefty song was originally written by country music artist Townes Van Zandt, and he also recorded it for his 1972 album The Late Great Townes Van Zandt. The 1983 duet of the legends, Nelson and Haggard, definitely popularized the song making it one of the most recognizable Texas songs ever.
In the music video depicting Nelson as Pancho and Haggard as Lefty, the original songwriter also appeared in a supporting role. Lana, Willie Nelson’s daughter, who also suggested the duet, directed the music video. The song reached number 1 on Billboard’s Hot Country Songs that year.
If you ever want to really get into country music, then these 10 best Willie Nelson songs will definitely help you out!