Willie Nelson songs
AP Photo/Ric Feld

20 of the Best Willie Nelson Songs

There are many reasons why Willie Nelson is a revered name in country music. They range from his 1962 debut to his part in founding the outlaw movement with future Highwaymen partners Waylon Jennings, Johnny Cash and Kris Kristofferson. Then there's some tales tell of his softer side with his sister Bobbie and the Family Band and his fellow Farm Aid co-founders. The Red Headed Stranger's legacy runs deeper than some might expect.

There's a slew of songs that Nelson has written over the years. Indeed, it seems for every song he's written that is undeniably his own, there's another iconic tune he's penned for another influential artist.

In other cases, it's his covers that Nelson's done particular justice. With a taste that ranges from the Great American Songbook to Coldplay, you can bet this legend has made his mark on a wide spread of songs.

There's just something everlasting about Nelson's talents. Since ...And Then I Wrote was released in 1962, the Texas outlaw has released over 170 albums, ranging from Christmas favorite Pretty Paper and country classic Yesterday's Wine to Gershwin brothers tribute Summertime and collection of standards Stardust. Among them are dozens of long-lasting hits that have secured his place as one of America's finest singer-songwriters ever to live. Here are 20 of the best Willie Nelson songs.

20. "Always On My Mind"

Although it's arguably the song Nelson is best known for, "Always On My Mind" isn't even a tune that he'd written himself. Penned by Denver songwriter Wayne Carson, Johnny Christopher and Mark James, the song was first recorded by Gwen Macrae in 1972. While Elvis Presley and Brenda Lee released their versions that same year, it was Nelson's rendition that broke records and went platinum a decade later.

19. "Angel Flying Too Close to the Ground"

Near the peak of his popularity in the mid-1980s, Nelson starred in a romantic drama called Honeysuckle Rose. Not only did he play the lead character, Buck Bonham, but he also wrote songs to feature in the film, including "Angel Flying Too Close to the Ground." The heartbreaking love song remains a staple in country music today, from Austin to Nashville and all around the world.

18. "Bloody Mary Morning"

Nelson originally wrote "Bloody Mary Morning" in 1970 to reflect his worries about parenting. When it was reworked for his 1974 album Phases and Stages, the song took on a whole new meaning, this time as a heartbreaking rambler about a jilted man left by his lover.

17. "Blue Eyes Crying in the Rain"

Nelson hit his stride in the mid-70s, and it's this song that is credited with revitalizing his career. Originally written by Fred Rose in the 1940s, other country greats like Hank Williams had already recorded renditions of the song. But it's Nelson's stripped-back take on this traditional country tune that resonates the most with listeners today.

16. "Blue Skies"

"Blue Skies" exemplifies Willie Nelson's knack for taking a tune from the Great American Songbook and transforming it into something that's all his own. The song was written in 1926, as a last-minute addition to the musical The Jazz Singer. Nelson's version gives the standard a bluesy, dreamy quality.

15. "City of New Orleans"

Nelson has covered some folk songs in his day, the most notable being Steve Goodman's "City of New Orleans." Arlo Guthrie had the first notable cover in 1972, but Nelson's 1984 recording brought the tune all the to No. 1 on the Billboard country charts. Goodman even won a posthumous Grammy Award for writing the song in 1985 as a result.

14. "Crazy"

Most songs that Nelson writes are best associated with his quirky twang and ability to sink just about any arrangement right into his offbeat phrasing. That said, "Crazy" is best known as Patsy Cline's breakout hit and for many a good reason.

13. "Funny How Time Slips Away"

Written by Nelson back at the start of his career in 1961, it wasn't until 2001 that he released a studio version of the song with collaborator Juice Newton. However, he's performed it for decades alongside many of his contemporaries. The track was well received by the country music community long before him and Newton's rendition. Fifteen other artists recorded the song before Nelson and Newton's take, including George Jones and Al Green.

12. "Georgia On My Mind"

It may not be as iconic as Ray Charles' take in 1960, but Nelson still offered enough gusto to this easygoing and soulful rendition that is often remembered by his fans as one of his very best covers.

11. "Good Hearted Woman"

Amongst all of The Highwaymen, it's Nelson's relationship with Jennings that may well be the most warmly regarded. The two put out a string of hits together, and it all started with "Good Hearted Woman" in 1971.

10. "Hello Walls"

Near the very start of his career in the early 1960s, Nelson was already exercising his songwriting muscle and shopping tunes around to other performers. Faron Young was one of the first to notably take on one of Nelson's tunes, with "Hello Walls," becoming a big success for him in 1961. It spent 23 weeks at the top of the Billboard charts. Nelson released his smooth-crooning version the following year.

9. "Last Thing I Needed the First Thing This Morning"

Nelson offers such a personal take on the heartbreak within the lyrics that one wouldn't be remiss to assume he'd written them himself. Instead, Gary P. Nunn wrote it with Donna Farar. More recently, Chris Stapleton offered his soulful rendition on From A Room, Vol 1.

8. "Mammas Don't Let Your Babies Grow Up to Be Cowboys"

Another hit record of Jennings and Nelson featured on their 1978 duet album of nearly the same name. The anthemic country swing tune went on to win a Grammy for Best Country Performance by a Duo or Group with Vocal.

7. "Mr. Record Man"

At the start of his career, Willie Nelson was down on his luck. Finding himself in poverty, he tried selling "Mr. Record Man" to Larry Butler, who instead gave him a job as one of his songwriters. When his songs proved to be successes for other artists, Nelson was recognized by Liberty Records and given his gig as a country singer. Henceforth, his take on "Mr. Record Man" was one of his first notable performances.

6. "My Heroes Have Always Been Cowboys"

Honeysuckle Rose wasn't the only movie for which Nelson wrote songs. Although his buddy Jennings first put out his take on the song in 1976, Nelson's version was featured in The Electric Horseman film. It's a reflection on the dream of being a cowboy set directly against a reality that many listeners may be able to relate to.

5. "On the Road Again"

What might very well be Nelson's most iconic song was written on a barf bag, of all things. Most noteworthy, though, is its rollicking "train beat" and enduring tale of travel. Those alone make it a country music chestnut for the ages.

4. "Pancho and Lefty"

Often seen as Townes Van Zandt's most well-known song, several dutiful interpreters have covered it over the years. All the while, it's Nelson and Merle Haggard's rendition for their collaborative Pancho & Lefty album that stands best alongside Van Zandt's as a stunning take on this classic outlaw ballad.

3. "Seven Spanish Angels"

After Nelson released his take on a Charles' "Georgia on My Mind," the two musical masters came together to perform a duet. The two artists crossover into each other's lanes magnificently on the track, culminating into a ballad that is just as much country as it is gospel and soul.

2. "Night Life"

Along with Cline's "Crazy," Ray Price's hit recording of "Night Life" established Nelson as an elite country music songwriter. It's since been recorded by not just Nelson but also Aretha Franklin and B.B. King.

1. "Whiskey River"

Originally recorded by Johnny Bush, Nelson put his stamp on this heartache-drenched country song back in 1973 on Shotgun Willie. Since then, it's become one of his go-to songs at live shows. This includes its sport as the opening track on the setlist for his live album Live at Billy Bob's Texas. As always, he puts his stamp on the song with this rollicking rendition worthy of any country road trip.

Honorable mentions: "Me and Paul" and "Family Bible"

Products featured on Wide Open Country are independently selected by our editors. However, when you buy something through our links, we may earn a commission.

This post was originally published on November 6, 2017. 

READ MORE: Willie Nelson's 60-Year Career Celebrated in New Vinyl Box Set