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 his partners Waylon Jennings, Johnny Cash and Kris Kristofferson. Then there are tales that tell of his softer side with his sister Bobbie and the Family Band. The Red Headed Stranger’s legacy runs deeper than some might expect.

There are a slew of songs that Willie has undoubtedly made his own. Yet, it seems for every song he’s written that is undeniably a Nelson song, there’s another iconic tune he’s penned for another influential artist.

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

There’s just something everlasting about Willie Nelson’s talents. Since …And Then I Wrote was released 55 years ago, the Texas outlaw has released a whopping 172 albums. Among them are dozens of long-lasting hits that have secured his place as one of America’s finest singer-songwriters to ever live. Here are 10 of the best Willie Nelson songs.

“Always On My Mind”

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

“Angel Flying Too Close to the Ground”

Near the peak of his popularity in the mid-1980s, Willie 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.

“Bloody Mary Morning”

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

“Blue Eyes Crying in the Rain”

Nelson hit his stride in the mid-70s, and it’s this song that is often credited for 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 Willie’s stripped-back take on this traditional country tune that resonates the most with listeners today.

“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.

“City of New Orleans”

Nelson has covered a number of old 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 charts. Goodman even won a posthumous Grammy Award for writing the song in 1985 as a result.

“Crazy”

Most songs that Nelson writes are best associated with his own 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.

“Funny How Time Slips Away”

Written by Willie all the way back at the start of his career in 1961, it wasn’t until 2001 that he released a studio version of the song alongside Juice Newton. However, he’s performed it for decades alongside many of his contemporaries. The track was received well by the country music community long before him and Newton’s rendition. It was recorded by 15 other artists prior to Nelson and Newton’s take, including George Jones and Al Green.

“Georgia On My Mind”

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

“Good Hearted Woman”

Amongst all of The Highwaymen, it’s Willie’s relationship with Waylon 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.

“Hello Walls”

Near the very start of his career in the early 1960s, Willie 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 Willie’s tunes, with “Hello Walls” becoming a big success for him in 1961. It spent 23 weeks at the top of the Billboard charts. Willie released his own smooth-crooning version the following year.

“Last Thing I Needed the First Thing This Morning”

Unlike other songs written by other names in the business, Willie Nelson was the first to offer up his take on this “cover.” He once again proves that he’s just as prolific a songwriter as he is an interpreter, offering such a genuine take on heartbreak that one wouldn’t be remiss to assume he’d written it himself. More recently, Chris Stapleton took on his own soulful rendition on From A Room, Vol 1.

“Mammas Don’t Let Your Babies Grow Up to Be Cowboys”

Another hit record of Waylon and Willie’s was 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.

“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 as job as one of his songwriters. When his songs proved to be successes for other artists, Willie was recognized by Liberty Records and given his own gig as a country singer. Henceforth, his own take on “Mr. Record Man” was one of his first notable performances.

“My Heroes Have Always Been Cowboys”

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

“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.

“Pancho and Lefty”

Often seen as Townes Van Zandt’s most well-known song, several dutiful interpreters of song have covered it over the years. All the while, it’s Willie and Merle’s rendition that stands best alongside Townes’ as a stunning take on this classic outlaw ballad.

“Seven Spanish Angels”

After releasing his own take on a Ray Charles tune, the two musical megatons 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.

“The Scientist”

Who knew that Willie Nelson and Coldplay would go together so well? At 76 years old in 2011, Willie brings a weathered and wizened version of this heart-wrenching contemporary classic. Consequently, it even rivals the quality of the original.

“Whiskey River”

Originally recorded by Johnny Bush, Willie Nelson put his stamp on this song back in ’73 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 own stamp on the song with this rollicking rendition worthy of any country road trip.

Now Watch: Remembering the Life and Music of Merle Haggard

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