Essential Willie Nelson Albums

Shotgun Willie may not have been the first outlaw country album, but it’s the one that got the ball rolling. Valuing grit and attitude over ’70s Nashville overproduction, Willie and The Family mix it up with The Memphis Horns, David Bromberg, Waylon Jennings, and Doug Sahm for a stew of honky tonk, Western swing, R&B, and rock ‘n’ roll, setting a template for the second act of his career and for the rebel incursion that would revolutionize country music.

Along the way, Nelson introduced tunes that would be his concert staples for decades to come, like his loose-limbed reinvention of Johnny Bush’s “Whiskey River,” and delivered one of the most goosebump-inducing versions of Leon Russell’s much-covered “A Song for You” that you’re likely to come across.

The third in the holy trinity of Nelson’s mid-’70s outlaw milestones that include Shotgun Willie and Phases and Stages, Red Headed Stranger is the most stripped-down and popular of the three. Like Phases, it’s a concept album. As literal an example of outlaw country as you’ll find, it follows a protagonist who murders his cheating wife and her man before going on the run.

Part of the album’s mastery lies in the way Nelson stitches the narrative together by combining his compositions with covers of country songs from other eras. The Fred Rose-penned “Blue Eyes Crying in the Rain,” for instance, goes back to the ’40s, but the lament suits both the singer and the story, and it became one of Nelson’s biggest hits. The tale retained so much staying power that Nelson starred in a movie adaptation more than a decade later.

Even though The Sound in Your Mind was a commercial success, over the years it occasionally gets lost in the shuffle. It may not reinvent the wheel like the trinity before it, but it stands tall alongside them. Freed from the conceptual restraints of Phases and Stranger, Nelson wandered wherever the spirit moved him, recording material that already made up much of his live show at the time. 

Whether Willie and The Family are tackling “Amazing Grace” or his hero Lefty Frizzell’s “If You’ve Got the Money (I’ve Got the Time),” they sound as natural as a tumbleweed in a ghost town. Plus, the medley of early Nelson classics, “Funny How Time Slips Away/Crazy/Night Life,” is a definitive slice of Nelson’s genius as a songwriter and performer.

In 1977, the outlaw country sound Nelson helped to pioneer was at its commercial peak. The world was hungering for more of that rough ‘n’ ready rebel style. Instead, he’d just gone on a pair of idiosyncratic detours, with an album of Lefty Frizzell covers and a gospel record. His next move was even further afield. Against record company advice, he cut an album of jazz/pop standards, long before such shifts were in vogue. 

In true Nelson fashion, he refused to slather the songs with strings and worked with his stalwart band plus the legendary Booker T. Jones on keys. Nelson’s twangy transformation of swinging staples like “Georgia on My Mind” and “Don’t Get Around Much Anymore” connected with the public on a level nobody could have foreseen, making Stardust a multi-Platinum crossover phenomenon and Nelson’s best-selling album ever.

For all the classic studio recordings in Nelson’s immense catalog, he’s arguably at his best on the road. His decades of endless touring have shown that he feels more at home on a concert stage than anywhere else. His shows are where he and The Family kick up their heels and let it all hang out. Willie And Family Live documents exactly that, recorded in 1978 when he and his band had fully come into their own as avatars of the outlaw country movement. Mickey Raphael’s wailing harmonica, Nelson’s sister Bobbie’s gospel-meets-boogie piano licks, and the frontman’s gritty guitar licks come into focus in a way they never did in the studio. Whether they’re jazzing up an oldie like “Crazy” or busting out a breakneck “Bloody Mary Morning,” this acoustic-based band overflows with electricity.

Nelson and Leon Russell had a lot in common when they teamed up on One for the Road. They were both deeply steeped in musical Americana of all kinds, each was a maverick duty-bound to follow his heart, and both casually redefined any outside material they touched. So, when they joined forces, all of the above naturally came through, times two. 

Together the duo tackled songs from the past that they held close to their hearts, rolling with easy aplomb through classic country, jazz standards, and more. Both men were also sons of the West, and they maximize that shared touchstone by gliding across a batch of cowboy tunes made famous by Western film legends like Roy Rogers (“Don’t Fence Me In”) and Gene Autry (“Ridin’ Down the Canyon”). And if all that weren’t enough, Bonnie Raitt pops up to lay down some spine-tingling licks on “Trouble in Mind.

Almost every country legend worth their salt has at least one Christmas album in their discography. But when Nelson set out to record his, he already had a huge advantage in his back pocket—he’d already written his own country Christmas standard. Back in the early ’60s, when he was a songwriter for hire, he’d placed “Pretty Paper” with Roy Orbison, who made it a hit and inspired loads of cover versions. 

Nelson built his 1979 holiday collection around his new recording of the song, surrounding it with well-known carols and pop Christmas classics. Nelson comes at these yuletide favorites nice and easy; like on the previous year’s Stardust, he keeps it small-scale, adding only Booker T. Jones to his usual crew. The result is the rare holiday record that makes even the well-worn staples sound fresh and joyful again.

Three years after the monumental success of Stardust, Nelson took another trip through the Great American Songbook with Somewhere Over the Rainbow. This time around, the arrangements were even more intimate (drums and piano are absent) and distinctly jazzier.

Two looming influences on Willie’s work at the time were Western swing originator Bob Wills and gypsy jazz guitar innovator Django Reinhardt, and he used this batch of standards as a new way to honor those inspirations. On tunes like “You’re Sorry Now,” Nelson injects the kind of jump Wills might have brought to the table, and it doesn’t hurt that Wills’ fiddler Johnny Gimble is on hand. Throughout the album, Nelson digs into swinging guitar lines that highlight his respect for Reinhardt’s style.

Nelson had expanded from country hero to mainstream superstar by the time he cut Always on My Mind. Despite the ubiquity of his previous hits, though, he’d not yet had a full-on blockbuster pop single. The album’s triple Grammy-winning title track changed all that. Nelson inhabited the tune’s mix of regret and compassion with so much warmth and earnest emotion it’s hard to believe he didn’t write it.

In actuality, producers had pitched the song to Nelson and Merle Haggard during a duo album session, but the latter vetoed it; Nelson eventually snapped it up for himself. The interpretive triumphs don’t end there—he wraps himself like an old bandana around an eclectic batch of covers, teaming with Waylon Jennings on Procol Harum’s “A Whiter Shade of Pale” and soulfully soft-pedaling the Aretha Franklin hit “Do Right Woman, Do Right Man.”

When Haggard broke through as country music’s convention-bucking Bakersfield bad boy in the mid-60s, Nelson still played by the rules on buttoned-up, Chet Atkins-produced records. But by the time they recorded Poncho & Lefty together, both were legendary for reshaping country music in their image. The title track that defines their first duo album gave another country iconoclast his break, Townes Van Zandt.

Van Zandt first released his cinematic Old West bandit tale “Pancho & Lefty” in 1972, but when Nelson and Merle decided to cut it a decade later, Van Zandt was still a struggling underground artist. The record brought him his largest payday ever. It also let two country giants bring all their gravitas to bear in an evocative Western epic for the ears that climbed to the top of the country charts.