Willie Nelson’s 10 Best Songs

By Sergio Ariza

Willie Nelson is the second greatest songwriter in country history, behind only the giant Hank Williams, but he's also a unique performer who managed to breathe new life into the genre from his exile in Austin. The fact that the guy who wrote Crazy more than 60 years ago is still with us, and recording new albums, is a miracle on a par with the fact that Trigger, his faithful guitar, still works - despite having holes the size of a golf hole! The fact is that we can still enjoy this country music legend and we want to celebrate it by choosing our 10 favorite songs from a repertoire that now counts 95 studio albums... and counting. 

10. Blue Skies (1978)

In 1978 Willie Nelson was, after 32 years of career, the most important country star in the USA. He was leading, together with Waylon Jennings, the 'Outlaw' movement and had recently released the first album of the genre that had sold more than a million copies. So when that year he decided to record, with Booker T. Jones as producer, an album of covers of standards from the American Songbook, many thought he was committing commercial suicide. He wasn't, and that wonderful record went platinum and give him two new number ones on the country singles charts, Georgia On My Mind and this Blue Skies. His version of the Irving Berlin classic is a true marvel, with his Family (his backing band) in excellent form, although the real stars are Nelson himself, who once again proves that he is as good a performer as he is a composer, and Trigger, his classic Martin N-20 with nylon strings, with which he plays a splendid solo in which he brings out the great
Django Reinhardt lover that he was.


9. Me & Paul (1971)

A song about life on the road (not the only one on this list) with his drummer and best friend, Paul English. Both the song, and the album that contains it (Yesterday's Wine), can be seen as the first glimpse of the outlaw Willie Nelson, more skeletal and outside the restrictions of Nashville - one of which was that they wouldn't let him record with his own musicians, like the Paul of the title. Although the album was a flop, which even led Nelson to temporarily retire from music, it was the one that gave him a break in his career and with which he began the magnificent run of conceptual works that would be the peak of his career, Shotgun Willie, Phases And Stages and Red Headed Stranger.


8. Hello Walls (1962)

Another one of those historic songs with which Nelson earned a few bucks and made a name for himself, in the early 60's, handing out hits to others. In this case the lucky one was the great Faron Young who recorded it in January 1960, shortly after hearing it from Nelson himself at Tootsie's Orchid Lounge, the bar across the road from the Grand Ole Opry, where the songwriter hung out. The song is a marvel in which a broken heart consoles itself by speaking to the lonely walls of its home. Nelson also recorded an exceptional version of his own for his 1962 album ...And Then I Wrote.


7. Angel Flying Too Close to the Ground (1980)

One of the most emotional songs of his career, composed for the Honeysuckle Rose soundtrack, and thought by many to be dedicated to his ex-wife Connie Koepke. Again the way Nelson caresses each word is sublime, as well as delivering yet another wonderful solo with Trigger. Suffice to say that the song was good enough for
Bob Dylan himself to cover it during the sessions for his 1983 album Infidels.


6. Funny How Time Slips Away (1962)

One of the greatest classics of Nelson's career, first recorded by Billy Walker in 1961, the composer made his own version the following year on the fundamental ...And Then I Wrote and since then it has seen hundreds of cover versions - catch your breath and see a small sample of the artists who have recorded this song, besides Walker and Nelson himself: Wanda Jackson, Joe Hinton, Brenda Lee, The Supremes, Stevie Wonder, Ray Price, Jerry Lee Lewis, Rick Nelson, Tom Jones. Georgie Fame, Joe Tex, Elvis Presley, Lulu, Bryan Ferry, Tina Turner, Johnny Cash,
B.B. King & Bobby Bland, Lucinda Williams and, above all, the torrid soul version by Al Green, for his 1973 album Call Me, proving, once again, that when a song is good it sounds good in any genre.


5. Time Of The Preacher (1975)

Time Of The Preacher
was the backbone of Red Headed Stranger, a concept album about a fugitive - the red-haired stranger of the title - who has killed his wife and her lover. Despite being an album with a story, Time Of The Preacher, is one of the few original songs on the album and appears several times in the development of the album. It is also the song that kicks off the album and the one that sets the tone for what is to come. It has an austere production - little more than Nelson's thrilling vocals accompanied by Trigger, until his regular bandmates come in, such as Paul English on drums, his sister Bobbie on piano and Mickey Raphael on harmonica. For once in a Nelson song the heartbroken man doesn't stay drinking and talking to the lonely walls, this time he saddles up his pony and ends the lives of his wife and her lover: "It was the time of the preacher in the year of '01. Now the lesson is over and the killing's begun".


4. I Still Can't Believe You're Gone (1974)

Red Headed Stranger
may be Nelson's great masterpiece, but his previous album, Phases And Stages, is almost on the same level. Another concept album, in this case about a divorce, with the first part taking the woman's point of view and the second, that of the man. I Still Can't Believe You're Gone pertains to the second part and is one of the most devastating songs in history, dealing with the tremendous impact that the departure of a wife has on a man - Nelson had not composed it specifically for the album, although it fits perfectly in it, but he did so after the suicide of his friend Paul English's wife.


3. On The Road Again (1980)

In 1980, at the age of 47, Nelson was at the peak of his popularity and was offered his first starring role in a movie called Honeysuckle Rose. During a plane ride the producer of the film approached him and asked him to write a song about life on the road to be used on the soundtrack - Nelson promptly grabbed one of the vomit bags and a pen and wrote the lyrics to this song before the plane landed. It is an enthusiastic and optimistic vision of being on tour, being one of the most cheerful songs in a canon full of sad songs and waltzes... However, with last year's pandemic, this song about concerts and touring took on a new meaning, as the Swedish band First Aid Kit recorded it to raise funds for the musicians most affected by not being able to play.


2. Blue Eyes Crying in the Rain (1975)

As we have said Willie Nelson is one of the most important songwriters in the history of country music, so it is a little strange that one of the biggest hits of his career, and the song that definitely made him a star, was a cover. But what Nelson did with this classic by the legendary duo Acuff/Rose was a full-fledged appropriation, making it the sentimental heart of his best album, Red Headed Stranger, re-stripping the style and bringing it to a new audience. The way he sings it is dark and desolate, but gives it a hint of hope as only he can do.


1. Crazy (1962)

is not only the best song Willie Nelson ever wrote, it is, quite simply, one of the best songs in the history of popular music - that is, however, in the glorious version of Patsy Cline, who is possibly the best female interpreter of the genre. Here you can appreciate Nelson's love of jazz and heartbreak from a young age. The melody is so good and classy that it could pass for one of those wonders from the pen of one of the greats of Tin Pan Alley, such as his beloved Irving Berlin or Cole Porter. Despite there being thousands of versions of his own songs by some of the biggest names in 20th century popular music (Elvis Presley, Aretha Franklin, Bob Dylan, Neil Young, Johnny Cash, Marvin Gaye...), Nelson himself admits that Cline's interpretation is his favorite of all. Of course, like many of his early hits for others, Nelson also recorded his own version of the song in 1962 for his album ...And Then I Wrote. He has also performed it countless times live, such as his duet with Sheryl Crow that we have included in our video selection.