If you were to create a list of the best country stars of all time, then Willie Nelson would have to appear on that list. His ability to tell a story in his songs and deliver his vocals to perfection stand out above almost every other country star to have ever performed.
But with so many different albums and songs having been produced over the decades, trying to narrow it down to his best tracks for the ultimate playlist was not easy. Yet, here we go with our list of the 25 best Willie Nelson songs of all time.
1. On the Road Again
This song was a huge hit, and it was one of those tracks that literally popped out of his head from nowhere. Those songs often work out to be the best, and it is just such a catchy track that it sticks with you once you have heard it for the first time. It is pretty simple to follow, but Nelson adds so much fun to it all as he recounts tales of traveling for shows and non-stop touring.
2. Always On My Mind
This classic Willie Nelson song was almost never his in the first place. Initially, the track was given to Merle Haggard who declined to record it. However, Nelson loved the concept and snapped it up instead. Almost like a country ballad, his voice is outstanding and injects just the correct amount of emotion at the right time.
Of course, it was a cover version of the Elvis Presley song, but the way he produced and sang the track led to his version winning a Grammy.
3. Whiskey River
This song represents classic Willie Nelson, and it remains one of his own favorite tracks. Released in 1973, he added a heavier bass line to the song before adding huge vocals as he worked his way through the verses. Viewed as a track with a bit more tempo than others, it has to appear on any Willie Nelson playlist.
4. Blue Eyes Crying in the Rain
This track was written by Fred Rose, and then Nelson came along in 1975 to make his own version, and he turned it into a classic. The song is a heavy, sad ballad that was different from his normal type of music since it appeared on a concept album. In the track, he managed to incorporate so much emotion that you cannot help but feel pulled along with him.
5. Blue Skies
Released in 1978, this track manages to pack so much emotion into it that you feel drawn into the song within the first few seconds. Nelson does this amazing thing with his voice where he sucks you in before softly guiding you through the track, leaving you feeling as if you are in a better place. It’s just gorgeous to listen to.
6. To All the Girls I’ve Loved Before
This song was a duet with Julio Iglesias, and the two of them somehow manage to get everything to work. With two completely different vocal styles, this slow ballad tugs on the heartstrings just as you would expect. It has to be one of the standout tracks by Nelson in his career and is a must for your playlist.
7. My Heroes Have Always Been Cowboys
This song was also recorded by Waylon Jennings, but it was Nelson who got it to number one in the charts. In the track, the concept of the cowboy is romanticized, and it certainly manages to get you to think about life as he takes you on this slow-tempo musical journey.
8. Angel Flying too Close to the Ground
This short song keeps things nice and simple, but in just a few minutes, Nelson manages to push across the story attached to the track of a man loving a woman. It’s a slow song designed to tug at your heartstrings, and that is something he is pretty good at with his numerous tracks. It’s a slow-burner that still pulls you along with so much skill and talent that you cannot help but feel touched by the song at the end.
This song may be one you associate with Patsy Cline, but that’s because Nelson pitched it to her. She released the track in 1961, and he did his own version in 1962, and it quickly became a fan favorite. Viewed as one of the best ballads ever written, the way he links in his vocals offset to the beat gives it an edge that is missing in her version. For music purists, his version is the better one, and yet we think you should just sit back and listen to how a song by two people can just sound so different.
10. Bloody Mary Morning
This track came at a time when Nelson was struggling with both his career and private life. For that reason, it’s a surprise that the song had so much of an up-tempo. Coming in his concept album, he incorporates a banjo into the track, which adds a whole new feeling to the song. Once again, he tells a story about himself, but this track would be one of those that would turn his entire life around.
11. Hello Walls
This song was first released in 1962 when it was only written by Nelson and performed by Faron Young. However, it became a major hit, and Nelson eventually released his own take on the track later. Viewed as a tragic comedic song, the original version reached number one on the country charts for nine weeks. Yet, it’s just cool to hear him sing his own track even if his version didn’t reach the heights of the original.
12. Pancho and Lefty
This version of the song was a duet between Nelson and Merle Haggard, and that’s almost like a dream team. They took this track about Mexican bandits to new heights, and it was one of the best outlaw songs to have ever been produced within country music. The double-tracked guitar solo produced by Nelson is brilliant, and the song has a finished feel to it without coming across as too polished. Overall, it’s a great version with the two of them working together with absolute perfection.
13. Who’ll Buy My Memories
This track was on an album released by Nelson to pay off his debts to the IRS, so that kind of explains the title of the song. It’s a magnificent track, considering what he was dealing with, and the combination of both piano and guitar is electric. It also includes Bobby Nelson, and it’s her on the piano, adding her own take on the music. Overall, it’s quite haunting and beautiful together, resulting in a stunning song that deserves more praise than it actually gets.
14. Forgiving You Was Easy
This ballad from 1985 showed Nelson at his best yet again. His crooning adds depth to the song as he talks about relationships and love, which are his favorite subjects. But as always, you cannot help but feel drawn into a track thanks to his voice adding a lot of emotion to the verses.
15. Darkness on the Face of the Earth
With a tinge of a Spanish two-step included in the music, the track is not as dark as the title appears to suggest. However, it still involves Nelson punching in a whole lot of emotion and feeling just because of his voice, and he’s an expert at doing that. Released in 1962, it’s catchy with a harmonious feel to it throughout with him inspiring you to spend time looking at things in the world with a bit more thought than you had perhaps been doing up until now.
16. Night Life
This song focuses more on the guitar than other instruments, and that’s partly the reason why it has been covered by so many other musicians. The track brings a whole lot of honky-tonk to the fore, but there’s more of an ambiance around the song that helps bring out the emotion in it. As always, Nelson is perfect with his vocals just having this ability to bring so much feeling to it all.
17. Half a Man
What we love about this track is the way it slowly moves along, giving Nelson the opportunity to croon in his familiar style while also telling a story throughout. This is classic storytelling via song, and his heavy vocals certainly add to the overall feeling you get while you listen. With some rockabilly thrown in, and listen out for the pedal steel, this is another fantastic track penned by him.
18. Family Bible
Nelson originally wrote this track for another country star, but he then decided he liked it so much that he had to do his own version. Released in 1971, it wouldn’t go on to be as big a hit as the original, but it was a song he held dear to his heart. That feeling is something that comes across in the way he plays the track, so we suggest listening intently to it in order to get a real feel for what’s going on.
19. Funny How Time Slips Away
This song from 1962 takes you back to the early days of Nelson, and even though it has been covered by numerous musicians, it is his version that stands out above all others. Throughout the track, he manages to really punch his way through the verses, giving the song a real sense of power with his delivery. Designed to be a ballad, the track has taken on a life of its own and is a must on your Willie Nelson playlist.
20. Roll Me Up and Smoke Me When I Die
Nelson works his magic again with a song that deals with the complexities of life, as he shows he still has what it takes to produce amazing music even decades after starting out. To say this track is beautiful is an understatement, but then that’s up to you to decide by checking it out.
21. Georgia On My Mind
This song from 1978 was Nelson doing a cover version of an already established track, but his version is viewed as one of the best. With the slow tempo, he has the time and space to add emotion and feeling through the song. It’s mellow and immediately memorable while also showing how different artists can put their own slant on the same track. It’s best played while comparing it to other versions to see just how good this one really is.
22. Pretty Paper
This track was originally for Roy Orbison, but Nelson managed to take the song and add his own country twist to it all. The is completely different from the Orbison version, and it has more of a sweetness to it along with giving it something of a Southern feel to the track. Also, there’s something of a warmth to his voice that adds a new layer of emotion to the song that is unmissable.
23. Good Hearted Woman
This song was actually a duet with Waylon Jennings, and the two of them worked perfectly in harmony with one another, as you would expect. But there was a twist, as Jennings had released the track some four years earlier and it involved some dubbing in production. It’s just a good old country song that jives along tugging on your emotions as you would expect from a double act such as this pair.
24. Getting Over You
This duet with Bonnie Raitt is wonderful. The two of them blend together with perfection but let’s not forget the use of pedal steel to ensure there are no gaps in the music. Also, she adds another level to the song by including her slide playing, and ultimately, it just leads to country music at its best.
25. Me and Paul
This track is all about being on the road, and it’s a dedication to his drummer, hence the name Paul appearing. In the song, it’s clear that his emotions are heartfelt and that the drummer played an important role in the development of his career. Incorporating some honky-tonk vibes, it’s a thoughtful track with some introspection throughout and is well worth checking out.
Barry has worked as a freelance writer for over a decade and has developed an eye for detail when it comes to unearthing cool and interesting facts.
His love of music stems from his student days checking out up and coming bands playing in the darkest corners of bars and clubs in Edinburgh.
The love of uncovering something new also remains with him. With an appreciation for music that’s best described as eclectic, his musical tastes range from Eric Clapton to Eminem through to Snow Patrol and Incubus. The memories that music can bring back to the fore is something he tries to portray in his writing.
For him, the voyage of discovery and unearthing something new is what makes this task of writing for MusicGrotto.com so interesting.