Willie Nelson's 10 Best Songs: Critic's Picks

Willie Nelson performs during the Luck Reunion on March 16, 2017 in Spicewood, Texas.
Gary Miller/Getty Images

Willie Nelson performs during the Luck Reunion on March 16, 2017 in Spicewood, Texas.

Willie Nelson. The name is six letters each for both first and last name, yet there is nothing simple about the man. In his career, he has defied – and continues to defy genres or classifications. He has recorded albums with just about every musical theme known to man since he began recording in the late 1950s. He has tipped the hat to Cole Porter and Ray Price, and recorded with artists ranging from Hank Snow to Snoop Dogg.

To dissect Nelson’s recorded legacy in a (somewhat) comprehensive manner, we decided to make this about Nelson’s greatest solo singles over the years. Artists such as Waylon, Johnny, and Julio all belong on a greatest hits list…...but let’s hold that for a duet one. Here are ten of his finest moments in the solo spotlight!

Best Songs: Alan Jackson | Blake Shelton | Brad Paisley | Carrie Underwood | Eric Church | George Strait | Jason Aldean | Johnny Cash | Kenny Chesney | Kenny Rogers | Lady Antebellum | Miranda Lambert | Rascal Flatts | Reba McEntire | Shania Twain | Tim McGraw | Toby Keith

10. Willie Nelson - "September Song"

The names Kurt Weill, Maxwell Anderson, and Walter Huston were not – and are not now, for that matter – known to Country audiences in 1979. And, Weill and Anderson’s composition – which Huston took to number one in 1950, and was also recorded by crooners such as Sinatra and Crosby – wouldn’t probably make many lists of "Great Willie Nelson songs." But, the singer DID record this one for the 1978 triumph Stardust, and did climb to the Top-20 on the Country singles chart with it. And, if you heard it back then – you know that this was one of his greatest performances.

9. Willie Nelson - "Forgiving You Was Easy"

For all the success and all the awards that have come Nelson’s way over the years, the most telling sign of his greatness is just how purely simple his songs are. There wasn’t a lot of production or overblown words on this 1985 number one hit, but there didn’t need to be. The singer wrote what he felt, delivered it on record, and simply let the listener be the judge. And, that’s sometimes all you really need to do.

8.  Willie Nelson - "One in a Row"

Deciding to limit this list to just Nelson’s solo work ensured that I would be able to select at least one track from his pre-beard early days on RCA Victor. Nelson never did hit the top ten during his days on the label, which was a shame – as the singer came up with some very interesting and vital work during his several years at the label. One of his biggest Nipper-related moments came with this Top-20 hit from 1966 that allowed the singer to shine in this Nashville Sound-themed recording. Perhaps it was the dramatic element of the arrangement that made his unique vocal phrasing stand out so. This is definitely one of his most under-rated moments.

7.  Willie Nelson - "My Heroes Have Always Been Cowboys"

As incredible of a wordsmith as Nelson has been in his career, the casual listener might be a little bit shocked that this ode to the lifestyle of the Old West does not include Nelson’s name as a writer. Instead, that honor goes to Sharon Vaughn, who crafted this finely-tuned lyric that inspired many who grew up drawn to the exploits of Rogers, Autry, and Bonanza.

6.  Willie Nelson - "On The Road Again" 

A Honeysuckle Rose inclusion, this song serves as proof of Nelson’s love of the road – and all that it entails. There’s something about the allure of the highway and the stage that has kept the singer going from one stage to the other – for years and years.

5. Willie Nelson - "Whiskey River"

A concert staple since the early 1970s, this is perhaps Nelson’s closest thing to a theme song that he has in his catalog. But, actually, it’s not his catalog. Fellow Texan Johnny Bush wrote and recorded an amazing version of the song prior to Nelson, but it’s the singer’s 1979 cover that fans will point to as one of the greatest stage kick-off songs in country music history.

4. Willie Nelson - "Angel Flying Too Close To The Ground"

From his Honeysuckle Rose film, this one remains one of Nelson’s greatest compositions. Walk down Nashville’s Broadway on any given night – and you will hear at least one country singer wanna-be performing this classic Willie Nelson song of heartbreak. Perhaps the singer at his most authentic and vulnerable.

3. Willie Nelson - "Always On My Mind"

Brenda Lee recorded it. Elvis Presley enjoyed a minor hit with it. But, in the hands of Nelson – one of the master song interpreters of all time – this record became one that was yielded into the Great American Songbook of the 1980s. His 1982 recording of this was an across-the-board hit for the singer, and also yielded Song of the Year trophies for writers Wayne Carson, Johnny Christopher, and Mark James – all for a song that had been a decade old at the time!

2. Willie Nelson - "Blue Eyes Crying In The Rain"

After two decades in the business as a successful tunesmith, Nelson finally broke through to the top of the Billboard Country charts with – what else? A Fred Rose classic made famous by Roy Acuff some three decades prior! There was nothing about Nelson’s sparse recording of this chestnut – or the Red Headed Stranger album that it was selected from - that rang with commercial aplomb when it hit the market in 1975, but perhaps that’s what we love most about Willie Nelson – There is no rhyme or reason to the chorus. We simply love the chorus.

1. Willie Nelson - "Georgia On My Mind"

So, you’re on top of the musical world, as Willie Nelson’s star finally was in 1978. Chances are you are not looking to revisit musical legacies from a bygone era – but then again, Willie has always danced to his own musical beat. His decision to release the classics album Stardust – and to dust off this Hoagy Carmichael ballad was probably not the wisest conventionally, but any conversation about Willie Nelson songs has to include this one – which is best played over a stereo in the dark, with one’s favorite beverage within reaching distance.