30. I Don’t Know a Thing About Love (2023)
At 90, Willie Nelson continues to record and tour – it might be a while before his ashes are being rolled between the Rizlas. His 2023 album finds him focusing on the songs of Nashville’s premier songwriter, the late Harlan Howard; this, its title track, is perfect Nelson: wry, reflective and beautifully sung.
29. Bring Me Sunshine (1968)
Originally recorded by the Mills Brothers and best known in the UK as Morecambe and Wise’s theme song, Bring Me Sunshine gave Nelson the last hit of his Nashville era. When he returned to the charts in the mid-1970s, the thriving counterculture of Austin, Texas, had transformed Nelson’s look and sound.
28. Always on My Mind (1982)
A decade after Elvis scored with this bathetic ballad, Nelson took uber-producer Chips Moman’s advice and recorded it. Nelson’s weathered baritone conveys a relatable heartache and he scored the biggest country hit single and album (of the same name) of 1982 while scooping several Grammy and Country Music Association awards.
27. I Am the Forest (1983)
Recovering from collapsed lungs, Nelson wrote the songs for Tougher Than Leather, his first album of original material in eight years. His band (which featured his older sister Bobbie Nelson on piano until her death in 2022) provide beautiful accompaniment on a song that captures Willie’s Texas Zen spirit.
26. On the Road Again (1980)
Honeysuckle Rose gave Nelson his first starring role in a feature film (playing a struggling country singer having an affair), but it’s this song that he wrote for the soundtrack – which encapsulates his desire to live life on a tour bus – that fans remember.
25. Across the Borderline (1993)
Nelson’s album produced by Don Was found him surrounded by famous fans; inevitably with such a project, it’s uneven. Yet Nelson sang the title track, a haunting lament – written by Ry Cooder, John Hiatt and Jim Dickinson for Freddy Fender – about migrants crossing from Mexico to Texas, with such grace that it’s now a modern standard.
24. The Harder They Come (2005)
Countryman, Nelson’s long-gestating reggae-country album (Chris Blackwell initially paired him with Sly & Robbie, to no avail), was generally regarded as a failure. Yet Nelson works wonders here, transforming Jimmy Cliff’s Jamaican outlaw anthem into a stark, sharp outlaw country song powered by snapping guitar and fierce, foreboding percussion.
23. Too Sick to Pray (1996)
If the 1980s found Nelson dominating the charts (don’t mention that Julio Iglesias duet), the 1990s were more musically adventurous. Spirit is a striking album featuring this fine track on ageing and mortality. His exquisite acoustic picking (on his battered Trigger guitar) reinforces just how gifted Nelson is as a musician.
22. Seven Spanish Angels (1984)
Nelson had long been in awe of Ray Charles when the producer Billy Sherrill paired them to sing this dramatic, mariachi-flavoured gunfighter ballad. Both men rose to the occasion and delivered exceptional vocal performances. A huge hit in the US, Canada, New Zealand and Australia, this is a stunning recording.
21. God’s Problem Child (2017)
Tony Joe White, Leon Russell and Jamey Johnson join Nelson – who left Nashville for Austin in 1972 – on this atmospheric slice of southern rock. Nelson’s interpretations of Russell’s A Song for You and Gregg Allman’s Midnight Rider demonstrate the shared country and blues roots he and the rockers share.
20. What Is This Thing Called Love (2018)
Nelson’s album My Way is a collection of Frank Sinatra’s hits – Sinatra being the singer who most influenced his vocal style. Here, teamed with his regular duet partner Norah Jones, he cooks up a joyous country-jazz boogie.
19. Immigrant Eyes (2019)
Across the decades, Nelson has recorded several songs by his fellow Texas songwriters and outlaw country poets Billy Joe Shaver and Guy Clark, neither of whom ever enjoyed his mainstream success. This sublime interpretation of Clark’s homage to ancestors who crossed from Europe to Ellis Island is intimate and deeply felt.
18. Bloody Mary Morning (1974)
Disillusioned by Nashville and his lack of success, Nelson briefly left music in 1971 to raise hogs. When he returned, he continued to struggle until Phases and Stages, a concept album reflecting on a couple’s divorce, produced this jaunty, bluegrass-flavoured boogie, his first significant hit of the 1970s.
17. Good Hearted Woman (1976)
Nelson and Waylon Jennings wrote this rousing celebration of their longsuffering wives in 1969, recording it individually. Remixed as a duet for The Outlaws, a compilation RCA threw together that quickly sold more than 1m copies, Good Hearted Woman hit big and helped Nelson and Jennings become American legends.
16. Blue Skies (1978)
Columbia’s executives feared Stardust, interpretations of songs from Nelson’s childhood, would be rejected by fans who wanted the outlaw they knew. But they loved it. Backed by a small combo, Nelson sings the Irving Berlin standard with a wistfulness few before or since have matched. One of his finest vocal performances.
15. Pancho and Lefty (1982)
Nelson’s prodigious output has seen him record duet albums with many of his contemporaries, Bakersfield’s Merle Haggard – a real outlaw, having served time in San Quentin – being a favoured partner. Townes Van Zandt’s ode to weary bandits suited these grizzled singers’ personas and gave Nelson and Haggard a US hit.
14. Shotgun Willie (1973)
With Arif Mardin producing and the Memphis Horns blasting, the title track of Nelson’s debut for Atlantic Records is a raucous celebration of Nelson the “hellbilly” (a term for wild southerners coined by Rob Zombie) – he had recently had a gunfight with a son-in-law. Kris Kristofferson referred to Shotgun Willie as “mind farts” while Nelson later declared it “more clearing my throat”.
13. Willingly (1961)
This duet with Shirley Collie, then soon to be Nelson’s second wife, is a country torch song consisting of little more than aching voices and double bass. Willingly gave Nelson his first US country Top 10 hit (although he would have to wait until 1975’s album Red Headed Stranger to establish himself as a bestselling artist).
12. My Heroes Have Always Been Cowboys (1980)
Robert Redford cast Nelson in The Electric Horseman, his first acting job, and he delivered an engaging turn as the wisecracking Wendell. This peach of a ballad became the film’s theme song, appropriately addressing themes of ageing and faded dreams, although Nelson was a youthful 47 when he sang it.
11. Hello Walls (1961)
Faron Young’s version of Nelson’s song of existential dread – a jilted lover addresses the walls, window and ceiling of his room, like a prisoner locked in torment – gave him a career-defining hit in 1961. Nelson has since recorded Hello Walls many times, including as a duet with Young in 1985.
10. Roll Me Up and Smoke Me When I Die (2012)
Nelson is joined here by his old pal Kristofferson and his new pal Snoop Dogg, the trio joyously sharing a wry philosophy on what to do with their ashes. Willie released the song on green vinyl for Record Store Day and named his 2012 memoir after this irreverent celebration of getting blunted.
9. Mammas Don’t Let Your Babies Grow Up to Be Cowboys (1978)
Nelson and Jennings were seen as the Butch and Sundance of outlaw country. The opening track (and biggest hit) of the first (and best) of their three duet albums is a joyous decrying of the outlaws’ wayward lifestyle. Reggie Young’s electric guitar fires things up nicely.
8. Me and Paul (1971)
Nelson’s homage to Paul English (Nelson’s drummer from 1955 until his death in 2020) is a witty, proto-rockabilly bromance about mishaps they endured while touring. English also served as Nelson’s enforcer. “If you’re writing songs about shooting people, it’s nice to have a guy who’s shot people up there on stage with you,” noted English’s son Paul Jr.
7. Cowboys Are Frequently, Secretly Fond of Each Other (2005)
Nelson first demoed Ned Sublette’s ode to gay cowboys in the mid-80s, finally releasing it (“I kept it in the closet,” he joked) in the wake of Brokeback Mountain’s success. A warm, insightful song addressing small-town mores, it won Nelson plaudits – he has long been country music’s most progressive voice – and brickbats.
6. Funny How the Time Slips Away (1961)
Nelson’s bittersweet ballad about encountering a former partner is one of his most covered songs – everyone from Elvis and Al Green to Bryan Ferry and Tina Turner has sung it. Nelson has made several versions – perhaps to do with him having been married four times.
5. Highwayman (1985)
Jimmy Webb’s mythic ode to reincarnation provided not just the name for a country supergroup comprising Nelson, Johnny Cash, Kristofferson and Jennings, but also gave the quartet a giant, Grammy-winning hit. Nelson sings the first verse as a mythic outlaw “hung in the spring of ’45, but still alive”.
4. Blue Eyes Crying in the Rain (1975)
Fred Rose’s 1946 ballad had been recorded by everyone from Hank Williams to Gene Vincent before Nelson cut the definitive version. Aching and sparse, it’s the centrepiece of Red Headed Stranger, a concept album about a killer on the run, and gave Nelson his first US country No 1.
3. Night Life (1960)
Nelson’s label rejected Night Life as “not country”, forcing Nelson to record it under the alias Paul Buskirk and the Little Men. Ray Price made it a hit in 1963 and everyone from Doris Day through Aretha Franklin to BB King has sung the immortal lines: “The night life ain’t no good life, but it’s my life.”
2. Georgia on My Mind (1978)
When Booker T Jones produced Stardust, an album of Nelson singing a selection of standards from the 1930s, his label was aghast. Yet Stardust won Nelson international stardom. Here, he sings Hoagy Carmichael’s ballad with such keen, understated grace that it established him as one of popular music’s great interpretive singers.
1. Crazy (1961)
During one week in 1958, despondent about his career and marriage, Nelson wrote Night Life, Funny How Time Slips Away and Crazy, three songs that would become standards. Crazy demonstrates his innate grasp of what makes a great country song. It’s short, melodic and heart-rending, a self-flagellating portrait of a breakup that the protagonist knows they should have seen coming. When he first offered it to other stars, Nelson struggled for interest – Nashville musicians disliked the complex minor chords and jazz-influenced phrasing – until a reluctant Patsy Cline turned his stately demo into an era-defining hit. Nelson’s first version, from his 1962 debut, is even slower: timeless moody blues brimming with heartbreak’s hurt and sorrow.
