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Top 10 Willie Nelson Songs

Willie Nelson
Robert Mora, Getty Images

Willie Nelson songs are some of the most beloved of all time. The iconic singer-songwriter and guitarist has recorded songs from across almost every genre over the course of his legendary career, touching on country, folk, jazz and standards.

Nelson’s catalog is so vast that it’s difficult to select just 10 songs to represent it. He’s not only one of country music’s greatest songwriters, he’s also one of the genre’s most inimitable vocal stylists and guitarists, making this list of the Top 10 Willie Nelson Songs that much more impressive.

Willie Nelson A Horse Called Music


“Nothing I Can Do About It Now”

From: ‘A Horse Called Music’ (1989)



Written by Beth Nielsen Chapman, this No. 1 hit from 1989 tells Nelson’s own outlaw saga pretty well, which is perhaps why it also happens to be one of the singer’s breeziest performances on record. Set to a cool Cajun-tinged groove, the tune finds a wistful Nelson resigned to his fate. With a personal life that has included four marriages, tax troubles and “high times” that have led to occasional brushes with the law, there’s obviously nothing he can, or would, do about all of it now.


Willie Nelson And Then I Wrote


“Hello Walls”

From: ‘And Then I Wrote’ (1962)



A 1961 crossover smash by Faron Young, this weird and wonderful little drama put Nelson on the map as a songwriter. In a one-sided conversation with the walls, windows and ceiling of a lonely, deserted room, the iconic artist pours his broken heart out, knowing “she’ll be gone a long, long time.” Nearly 50 years later, the pain still feels brand-new and very real.


Willie Nelson Merle Haggard Pancho & Lefty


“Pancho and Lefty” (With Merle Haggard)

From: ‘Pancho & Lefty’ (1983)



One of the greatest story songs ever written by — and originally from a 1972 album titled — The Late, Great Townes Van Zandt, Nelson shares vocals on this track with the legendary Merle Haggard; the two made it the title track of a duets album they released in 1983. A haunting tale of bandits and betrayal, what’s really going on in the story is far from clear. But while the details are murky, the song captures two musical giants in their prime.


Willie Nelson The Troublemaker


“The Troublemaker”

From: ‘The Troublemaker’ (1976)



The title track from Nelson’s country-gospel album was released in 1976 but recorded three years earlier, when the Vietnam War was perhaps at its most controversial point. The title character of this sparse but electrifying tune is a long-haired, peace-loving rebel who wears sandals, travels with a motley group of friends, rejects the establishment and has “never held a job.” The last two lines are guaranteed to raise a few goosebumps.


Willie Nelson Willie and Family Live


“Whiskey River”

From: ‘Willie and Family Live’ (1978)



Leave it to Willie and Family to score a hit with this great live recording all about the tortured memories of that “amber current.” Another song not written by, but forever linked to, Nelson, the jaunty feel of the version most familiar to fans masks the tune’s tragic message. A longtime concert staple, Nelson has left fans intoxicated with several recorded versions of the Johnny Bush classic.


Willie Nelson Red Headed Stranger


“Blue Eyes Crying in the Rain”

From: ‘Red Headed Stranger’ (1975)



From Nelson’s landmark 1975 concept album, Red Headed Stranger, a disc that should be in every music fan’s record collection, this tune, written by Fred Rose and originally recorded by Roy Acuff, was already 30 years old when Nelson made it his own. His is the definitive version, becoming his first No. 1 hit as an artist and elevating “Red Headed Stranger” to iconic status.


Willie Nelson Honeysuckle Rose


“Angel Flying Too Close to the Ground”

From: ‘Honeysuckle Rose’ (1980)



Perhaps the saddest song Nelson has ever written and recorded, “Angel” tells a story of the healing power of love, and the bittersweet memory that remains when the healing is done and it’s time to move on. Remarkably, the 4:29 single version, a No. 1 country hit, includes a full one-minute solo of Nelson’s distinctive acoustic guitar, further enhancing its mournful beauty.


Willie Nelson On the Road Again


“On the Road Again”

From: ‘Honeysuckle Rose’ (1980)



The perfect theme song for a performer and his “band of gypsies” who have spent decades traveling across the country and around the world entertaining millions of fans. Taken from the Honeysuckle Rose soundtrack, in 1980 the song became Nelson’s ninth No. 1 country hit, and was a Top 20 pop hit as well. It has continued to travel well — in 2004, Rolling Stone ranked it among the 500 Greatest Songs of All Time.


Patsy Cline Showcase



From: ‘Showcase’ (1961)



One of the greatest country songs ever written or recorded, and (according to Rolling Stone) No. 85 among the 500 Greatest Songs of All Time. A career-changing hit for Patsy Cline in 1961, the year Nelson wrote it, the song remains a popular jukebox hit and a favorite of karaoke performers. Nelson wrote “Crazy” when he was still a struggling songwriter, and pitched it to Cline’s husband after running into him at Nashville’s famed Tootsie’s Orchid Lounge.


Willie Nelson Always on My Mind


“Always on My Mind”

From: ‘Always on My Mind’ (1982)



Nelson didn’t write it, and Elvis Presley, Brenda Lee and the Pet Shop Boys are among the hundreds of artists who have recorded it, but Nelson’s version remains the quintessential rendering of this tender, pleading ballad. A Top 5 pop hit, Nelson’s cover was Billboard‘s No. 1 country song of 1982, and a CMA Award winner in 1982 and 1983, as well as a Grammy recipient. Awards aside, it remains one of the most evocative, beautiful performances of his career.


NEXT: 25 Things You May Not Know About Willie Nelson

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