top of page

20 Great Willie Nelson Songs

"Willie Nelson could, as they say, sing the phone book and make you weep – he could also write the phone book."


This great line by a great writer - none other than Bob Dylan – says it all.


Maybe Bob should have added: Willie could sing with anybody in the phone book!


At last count (and don’t hold your breath), Willie has released 99 studio albums, consisting of 73 solo and 26 collaborative albums. Add to this, 14 live and 51 compilation albums, as well as a couple of film soundtracks – The Electric Horseman and Honeysuckle Rose. In the U.S. alone, he has sold more than 40 million albums.


And if you multiply his output by, say a consecutive 10 per album, you get an incredible total of 1,640 plus songs. So, try and choose 20 Greats from all these.


Crossroads wanted to represent Willie across the various genres – from raw country to gospel – in his catalogue, as well as find a balance between self-penned and covers. Then there is the fabulous selection of duets to consider!


And it is all to celebrate a very special date – April 29, 2023. 

Happy 90th Birthday Willie Nelson

Photo Credit: Willie Nelson getting ready to perform. Farm Aid 2009. Photo by Larry Philpot,

Blue Eyes Crying in the Rain

Fred Rose’s weepy classic was made popular by Roy Acuff in 1947 and Hank Williams did a sensational live version four years later. But neither can compare with Willie’s astonishingly-sparse treatment for the conceptual Red Headed Stranger – the album which kick-started his legendary career. The song would become his first number one as a singer - he had already composed a string of hits for other artists – and was the third biggest seller in the 1975 Billboard Hot Country Singles chart. Rolling Stone placed it in its 500 Greatest Songs of All Time. Enough said.

Red Headed Stranger  

This is the title track from Willie’s album which is regarded by many as the greatest Country album ever released. The song, written by Edith Linderman Calisch and Carl Stutz in 1953, had always been one of Willie’s favourites and he would sing it to his young children. In 1974 his then wife Connie Koepke suggested he write a western concept album based on the song, which tells the tale of a fugitive on the run after killing his wife and her lover.  He did so – mixing old songs with original compositions – to produce not only a blockbuster album but one which would establish the right of an artist to be given complete creative control. The story goes that when Willie first presented it to Columbia, the record company thought it so sparse, it was a demo. It wasn’t and it was released as is - Willie and manager Neil Reshen had negotiated creative control. Back to the title-song and Edith’s lyrics, which include one of the most wonderful stanzas in country music:

The yellow-haired lady was buried at sunset/The stranger went free, of course

For you can’t hang a man for killin’ a woman/Who’s tryin’ to steal your horse

Funny How Time Slips Away

In his autobiography Willie recounts how he wrote some of his blockbuster songs – the likes of “Funny How Time Slips Away,” “Crazy” and “Night Life” – in a song-writing blitz while working as a DJ in Houston shortly before he moved to Nashville in 1960. Willie’s version of “Funny How Time Slips Away” was included on his debut studio album … And Then I Wrote, released in 1962.  But the song was first a single for Billy Walker a year earlier. The much-hyped Elvis Presley’s version surfaced on Elvis Country in 1970 and several big names, from Bryan Ferry to Brenda Lee, also included it in their recording catalogues. But, again, it is Willie’s version most remember.


These days, the saying goes that all songwriters in Nashville want Emmylou Harris to record their compositions. Sixty years ago, the artist of choice was Patsy Cline. Willie wrote “Crazy” before he left Texas for Nashville in 1960. He says he wrote it in an hour. (And remember this is a tune with several chords). Within 18 months, the song had reached Cline through an elaborate route involving Willie’s friend, singer-songwriter Hank Cochran, and Cline’s husband Charlie Dick. How Cline’s version finally got recorded would make a fascinating mini-series in itself. Suffice to say it would become her most successful pop single and in 1996 it was cited as the most played song ever in American jukeboxes. There are various versions of “Crazy,” as might expected for a song generating among the most royalties for a country song. And, it is no surprise that Willie has always regarded Patsy’s version as his favourite. Willie’s own rendition - on his 1962 debut album - came a year after Cline’s.

On the Road Again

This is one of Willie’s most recognizable tunes and indeed has become an anthem for touring musicians. He wrote it for the soundtrack to the 1980 film Honeysuckle Rose in which Willie had a leading role as an aging travelling musician. It was released in the same year on the Willie Nelson & Family Honeysuckle Rose album and reached #1 on the Billboard’s Top Country Albums. It had already been a hit single for him. It would win him a Grammy for Best Country Song and be nominated for Best Original song at the 53rd Academy Awards. In 2011, “On the Road Again” was inducted into the Grammy Hall of Fame.

Always on My Mind

Bob Dylan said it best when he wrote in The Philosophy of Modern Song: “He (Willie) sang the song Elvis had a hit with, ‘Always On My Mind.’ All you remember now is the Willie version.” Willie’s was released in early 1982, more than 10 years after Elvis. But it still shot up the Billboard charts and would win three Grammy Awards in 1983. Willie won for Best Male Country Performance, while songwriters Wayne Carson, Johnny Christopher and Mark James got Grammys for Song of the Year and Best Country Song. There are more than 300 recorded releases of “Always On My Mind” which was inducted into the Grammy Hall of Fame. But Willie’s version, as Bob says, sits above them all.

Sad Songs and Waltzes

This wonderful song, written by Willie, was somewhat overshadowed by the likes of “Whiskey River” and the title track on his impressive 1973 album Shotgun Willie. But in 1996, it got an unlikely resurgence when the group CAKE released a competent cover. “Sad Songs and Waltzes” is, as might be expected, in three-quarter time and again demonstrates Willie’s ability to cleverly improvise lyrics from any given situation. In this case, selling records:


I’m writing a song all about you/A true song as real as my tears

But you’ve no need to fear it/ ‘cause no one will hear it

‘Cause sad songs and waltzes aren’t selling this year

Mamas Don’t Let Your Babies Grow Up to be Cowboys, featuring Waylon Jennings

The statistics of this wonderful ditty by Ed and Patsy Bruce say it all. As the opening track on the famous 1978 duet album Waylon & Willie, “Don’t Let Your Babies Grow Up to Be Cowboys” propelled the album to #1 on the US country album charts for 10 weeks and it stayed in the charts for some 126 weeks. And as a single, it spent four weeks at the top of the country charts in March 1978. It also made the Billboard Hot 100 pop charts, peaking at 42, and would win a Grammy in 1979 for Best Country Performance by a Duo or Group with Vocal.How the pair from rival record companies –  RCA (Waylon) and Columbia (Willie ) – came to record an album together is another story in itself.

Uncloudy Day

If ever there was a song in Bob Dylan’s mind when he said Willie could sing the phonebook, then it is probably the gospel standard “Uncloudy Day.” Dylan was in awe of the famous 1956 version by the Staples Singers. Willie’s version came 20 years later. Though vastly different to the Staples family, it is equally impressive – helped by some superb backing, both instrumental and vocal. Tex-Mex legend Doug Sahm and his band comprised most of the session musicians. But a special feature is some beautiful piano from Willie’s sister Bobbie, a life-time member of his backing band. Bobbie died in 2022, aged 91. “Uncloudy Day” was the opening track on the 1976 release The Troublemaker, yet another Billboard #1 on the US Country Albums chart. It was also the album’s single and reached #4 on the Hot Country Singles. He later did a more rambunctious version with Dyan Cannon for the 1980 film Honeysuckle Rose in which they co-starred together.

Pretty Paper

The story goes that Willie wrote this enchanting ballad after seeing a disabled man crawling along a Fort Worth sidewalk. The man would call out “pretty paper” as he sold ribbons and wrapping-paper to passers-by. Nelson wrote it in 1963 and when producer Fred Foster first heard it, he decided to immediately pitch it to Roy Orbison who made it a hit. Nelson recorded his own version – produced by Chet Atkins - a year later. In 1979, he re-recorded it as the title track for his first Christmas album. He would do yet another recording with sister Bobbie for their 1997 Hill Country Christmas album. Over the years, it has become a standard Christmas song, recorded by countless artists - one of the best by Canadian-Kiwi Tami Neilson, who achieved a life-long ambition in 2022 when Willie joined her for a duet on “Beyond the Stars.”

Hard Promises to Keep, featuring Kimmie Rhodes

Willie put his Americana hat firmly on his head when he joined Kimmie Rhodes on her majestic 1996 album West Texas Heaven, a collection of 12 original Rhodes songs. It also features Texas legends Townes Van Zandt and Waylon Jennings. Willie does two duets with Rhodes – the other “I Never Heard You Say.”  But “Hard Promises to Keep” has to be the most beautiful and indeed perhaps the best of all his duets with female artists over the years. The subtle arrangement, helped immensely by Willie’s distinctive virtuoso guitar, is as soothing as the endearing vocals. And a weeping pedal steel further harmonizes Kimmie’s gentle lyrics:

I thought you’d want them back some day

I kept them for you anyway

But I know when I’ve been given hard promises to keep

Pancho and Lefty, featuring Merle Haggard 

The Ken Burns doco series History of Country Music nicely recounts how Willie and Merle came to have a hit with one of the finest country ballads ever written. But the pair did not model it on the original Townes Van Zandt version, but rather the spectacular cover by Emmylou Harris. In 1983, Willie and Merle were putting the final touches to a joint album, but they were short of a song to hang the whole project on. One night, Willie’s daughter Lana played him a song he had not heard - Emmylou’s version of “Pancho and Lefty.” Willie was so impressed he woke up Merle at 4am and insisted on recording it then and there at Willie’s studio in Texas. The song would become the album’s title track. It went straight to number one on the country charts, crossed over to pop and sold more than a million copies. And it was this version that got inducted into the Grammy Hall of Fame in 2020.

Seven Spanish Angels, featuring Ray Charles

Troy Seals and Eddie Setser had originally written “Seven Spanish Angels” as a homage to the Marty Robbins classic “El Paso.” They would have preferred that Robbins record it, but Marty was deceased. They soon successfully pitched it to Willie. Big-time producer Billy Sherrill then heard a demo and wanted it for Ray Charles. When he discovered it was reserved for Willie, he proposed a duet. Ray and Willie split both the verses, each also doing a chorus with backing singers. Ray then does another chorus before inviting Willie back for an outro. It is goose-bump listening. "Seven Spanish Angels" was released as a single from Ray’s 1984 album Friendship. It was the most successful of Charles' eight country hits. The single spent one week at number one and a total of twelve weeks on the country chart.

Me and Paul 

Willie has never been shy about poking fun at himself in song – listen to “Still Not Dead” from 2017. “Me and Paul” reflects on his life on the road with long-time drummer Paul English, who died in 2020, aged 87: 

I guess Nashville was the roughest/But I know I’ve said the same about them all

We received our education in the cities of the nation/Me and Paul.

The song is the title track of his 32nd album which was released in 1984, a period where Nelson is regarded as being at his performing pinnacle, helped indeed by English.  A successful nation-wide tour to promote the album only reinforced this, culminating with a much-acclaimed concert at New York’s Radio City Music Hall. 

Whiskey River

There has to be a place for “Whiskey River” in any Willie list, given that the man himself has long used the song to open his concerts. Though he didn’t release it as a single until 1978, it was originally recorded for the 1973 album Shotgun Willie, his first release for Atlantic – manager Neil Reshen having resolved his issues with RCA. The song was actually written by – and a top 10 hit for – “Country Caruso” Johnny Bush who had offered it to Willie the previous year. “I took the song the way it was, but adapted it to my style which was more blues than rock,” Willie told biographer David Ritz. It was a style to be adored by concert fans the world over.

Hello Walls 

This classic is as famous for its back story as it is for Willie’s simply gut-wrenching lyrics about a jilted man so lonely he talks to his bedroom – walls, windows, ceiling et al. The story goes that Willie was so broke in 1961 that he offered to sell the song to Faron Young for $500 -  Young having just released” Hello Walls”  as a single on his album of the same name. Feeling sorry for Willie, Young loaned him the 500 dollars so he could keep the publishing rights. It was about to became a massive #1 hit for Young, staying 23 weeks in the country charts. And within a few months, Willie received a royalty check for $20,000. How Willie thanked Young is nicely recalled in Faron’s biography. “I was sitting at Tootsie’s (a bar) and a big hairy arm came around my neck, and Willie French-kissed me. It’s probably the best kiss I ever had!” The song would turn out to be one of three – the other two being “Crazy” and “Funny How Time Slips Away” – royalty-rich tracks on Willie’s intriguing 1962 debut album.

Angel Flying Too Close to the Ground

This is another from Honeysuckle Rose and is one of eight he wrote out of the 24 tracks on the movie soundtrack. And while “On the Road Again” became the album’s blockbuster, “Angel Flying Too Close to the Ground” is often singled out for Willie’s stunning vocal performance. After all, he did have some of his most heart-breaking, yet endearing, lyrics to interpret.

Fly on, fly on past the speed of sound/I'd rather see you up than see you down
Leave me if you need to, I will still remember/Angel flying too close to the ground

Night Life

Of all the great lines penned by Willie, this has to be one of the finest:

The night life ain’t no good life, but it’s my life.


Like “On the Road Again,” it would serve as an anthem for entertainers the world over. Willie wrote it while balancing life as a day-time disc jockey and a nightclub singer around Houston in the late 1950’s. As with “Hello Walls,” it had a murky upbringing, being first sold by Willie to guitar instructor Paul Buskirk and then a short-time later on-sold to Ray Price who made it a hit and the title track of his 1963 album. Willie’s first release, under his own name, was as a single that same year. It would be included on his 1975 compilation album Country Willie: His Own Songs. Notable covers include Aretha Franklin, Frank Sinatra and BB King.

Angel Eyes, featuring Emmylou Harris 

This beautiful song written by fellow-Texan Rodney Crowell was another featured in the Willie movie Honeysuckle Rose, in which Emmylou Harris plays herself. Emmylou had released a solo version on her 1979 Christmas album Light of the Stable and Waylon Jennings also did a rendition on It’s Only Rock & Roll four years later. But there is something magical about Willie’s duet with Emmy, rated by Rolling Stone magazine as “arguably the greatest American harmony singer of the past half-century.” The high notes she hits alongside Willie only serve to justify this claim. 

Django and Jimmie, featuring Merle Haggard

This is the title track off the sixth and final collaborative studio album by Willie and Merle. It was released in June 2015, just 10 months before Merle died, and would be his last studio album. “Django and Jimmie” is a tribute to Django Reinhardt and Jimmie Rodgers, written by Jimmy Melton and Jeff Prince. It was forwarded to Willie and Merle by producer Buddy Cannon and their interest in the song proved the catalyst for their final album together. The charming lyrics indeed honour the pair as much as they do Django and Jimmie:

Might not have been a Merle or Willie

If not for a Django or Jimmie



The dates accompanying each song refer to the year of release.


Crossroads respects all creative copyright by songwriters and performers and lyrics and recordings are used for review purposes only.

Any factual errors and omissions are regretted.

bottom of page