The first band Willie Nelson joined played polka. He was only 10, but he brought several years of experience to the group.
His grandparents bought him a guitar from Sears when he was 6, and he started writing his own songs the year after that. He hasn’t stopped since. Almost 300 albums, more than 2,500 songs, seven decades, and countless of miles later, Nelson is one of the most recognized and revered figures in the world, let alone music.
Nelson landed at No. 7 as the latest honoree on CMT All-Time Top 40: Artists Choice, a list of the most influential artists in history chosen by country stars themselves. Another honoree is named each week on CMT Hot 20 Countdown.
With such a massive catalog of songs and recordings, narrowing down his accomplishments to a short list is a challenging task, but in chronological order, here are 10 performances that have defined his career over more than five decades:
Nelson was relatively unknown when he wrote “Crazy.” In 1962, Patsy Cline was already a star and delivered the powerfully plaintive vocals we all know in one masterful take. She didn’t immediately warm to Nelson’s demo of the song, in which he monkeyed with phrasing — sometimes jumping the beat, sometimes lagging behind — but Owen Bradley, her legendary producer, heard potential. As for Nelson’s writing, he took country’s tear-in-my-beer sadness, mixed it with pop elegance and jazz irreverence to create an exquisite exercise in self-deprecation as well as one of country music’s most famous songs ever.
Its unmistakable percussive guitar and crazed songbird harmonica kick off almost every one of Nelson’s live shows, sometimes in a jazz-inspired rush, other times in a blues-soaked stroll. Nelson always picks the pace. Written by fellow Texan Johnny Bush and Paul Stroud, “Whiskey River” appeared on the 1973 album Shotgun Willie, Nelson’s decisive pivot from Nashville convention and toward the creation of Outlaw country. No, Nelson didn’t write “Whiskey River,” but like so many other songs composed by others that he’s recorded, it’s all his.
“Blue Eyes Crying in the Rain”
Just a sparse acoustic guitar and an inviting, campfire tenor carry this song, which became his first No. 1, earned him his first Grammy and introduced the world to Nelson as a recording artist. On the watershed 1975 album Red Headed Stranger, the song takes lovers’ separation to especially forlorn depths: “Love is like a dying ember, only memories remain/And through the ages I’ll remember blue eyes cryin’ in the rain.” Elvis Presley, Roy Acuff and others have also recorded the tune, which was written by Fred Rose, but Nelson’s aching rendition is the one that’s hung around.
“Mammas Don’t Let Your Babies Grow Up to Be Cowboys” (with Waylon Jennings)
If you don’t smile when listening to Jennings join his friend for a song, honky-tonk may not be your bag — or you may just need to check your pulse. The two won a Grammy for this 1978 No. 1 smash written by Ed and Patsy Bruce, wryly admonishing and romanticizing cowboys in a rollicking warning for moms who probably weren’t considering pushing cowpoking as a career in the first place.
“Georgia on My Mind”
In 1978, Nelson also released Stardust, an album that took his flirtations with jazz, rhythm and blues, rock and pop, blended them with his country core and unveiled an entirely new sound that he’d been inching toward for years. He was already an outlaw and a superstar. Now he was an artist on par with the best. His haunting cover of Hoagy Carmichael’s “Georgia on My Mind” — an American classic indelibly sung by Ray Charles — won a Grammy, and Stardust stayed on country charts for a decade.
“On the Road Again”
Legend has it Nelson wrote “On the Road Again” in about 20 minutes on an airplane barf bag. The signature song with a runaway train beat was featured in Nelson’s 1980 film, Honeysuckle Rose. The recording notched him his fourth Grammy, as well as his first and only Academy Award nomination for best original song. These days, he usually winds down most shows with this autobiographical tribute to highways, old friends and new towns — a fitting farewell that captures his undiminished anticipation and love of performing.
“Always on My Mind”
Sister Bobbie Nelson kicks off this No. 1 hit from 1982 on the piano before her brother launches into a list of concessions about falling short as a lover. But, he pleads earnestly, he was thinking about her the whole time. His delivery clinched another Grammy, his fifth, and firmly cemented his role as the outsider insiders love to love. Written by Wayne Carson, Johnny Christopher and Mark James, Elvis Presley offered a moving cover of the song not long after his separation from Priscilla, while Brenda Lee and the Pet Shop Boys have recorded it, too.
“Pancho and Lefty” (featuring Merle Haggard)
One of the greatest story songs ever written, “Pancho and Lefty” paired Nelson with fellow icon Haggard. A genius consistently ranked among the best songwriters to have ever lived, Townes Van Zandt penned the hardscrabble tale about bandits, betrayal and living with decisions made and originally recorded it in 1972. Nelson and Haggard’s definitive version plays like a John Ford film for your ears and climbed all the way to No. 1 in 1983.
“Highwayman” (with Kris Kristofferson, Waylon Jennings and Johnny Cash)
Along with Kristofferson, Jennings and Cash, Nelson formed the Highwaymen, Outlaw country’s version of the Rat Pack, in the ‘80s. The quartet’s single “Highwayman” — a trippy tale of reincarnation written by Jimmy Webb — topped the charts in 1985. All four take a verse with distinct style and swagger, and the result is an anthem celebrating the soul’s immortality that’s taken on an air of heightened poignancy with the passing of Jennings and Cash.
“Mendocino County Line” (featuring Lee Ann Womack)
Nelson is a generous and frequent collaborator. In addition to those on this list, his duet partners have ranged from Ray Charles, Julio Iglesias, Ray Price and Leon Russell, to Snoop Dogg, Rob Thomas, Wynton Marsalis and Toby Keith. For 2002’s “Mendocino County Line,” he called on Womack. The dreamy remembrance of long-gone love sweeps listeners away thanks to Womack’s lush vocals. Ultimately, though, the track is grounded in the gritty, glorious Nelson — the eternal, offbeat metronome of American music.