As a performer and a songwriter, Merle Haggard was the most important country artist to emerge in the 1960s, and he became one of the leading figures of the Bakersfield country scene. While his music remained hardcore country, he pushed the boundaries of the music quite far. Like his idol, Bob Wills, his music was a melting pot that drew from all forms of traditional American music -- country, jazz, blues, and folk -- and in the process, developed a distinctive style of his own. As a performer, singer, and musician, he was one of the best, influencing countless other artists. Not coincidentally, he was the best singer/songwriter in country music since Hank Williams, writing a body of songs that became classics. Throughout his career, Haggard was a champion of the working man, largely due to his rough-and-tumble history.

It's impossible to separate Haggard's music from his life. He was born to James and Flossie Haggard on April 6, 1937. His parents moved from Oklahoma to California during the Great Depression, converting an old boxcar into a home. Before their marriage, James played fiddle in local honky tonk bars. Flossie was a member of the Church of Christ, which led to her forcing her husband to stop playing the honky tonks. James died from a brain tumor when Merle was nine years old. After his father's death, Merle became rebellious. In an attempt to straighten her son out, his mother put him in several juvenile detention centers, but it had little effect on Merle's behavior. As a teenager, he fell in love with country music, particularly Bob Wills, Lefty Frizzell, and Hank Williams. When he was 12 years old, Haggard was given his first guitar by his older brother; Merle taught himself how to play by listening to records that were lying around the house.

Even though he had begun to pursue music, Haggard continued to rebel, running away with his friend Bob Teague to Texas when he was 14 years old. A few months later, the pair returned to California, where they were arrested as robbery suspects. After the real thieves were caught, Haggard was sent back to juvenile hall, but he and Teague took off to Modesto, California. For a brief time, he did manual labor, was a short-order cook, drove a truck, and committed a series of small crimes. Soon after he moved to Modesto, Haggard made his performing debut with Teague at a bar named the Fun Center; the two were paid five dollars and given all the beer that they could drink.

By the end of 1951, Haggard had returned home and he was again arrested for truancy, as well as petty larceny. In the beginning of 1952, he was sent to Fred C. Nelles School for Boys in Whittier, California; again, he ran away. This time, the courts decided he was incorrigible and sent him to the high-security Preston School of Industry; he was released after 15 months. Shortly after his release, he and a boy he met at PSI beat up a local boy during an attempted robbery, and Haggard was sent back to PSI.

After getting out of PSI for the second time, Haggard had the first major event in his musical career. He went with Teague to see Lefty Frizzell in concert in Bakersfield. Before the show, he went backstage with several friends and he sang a couple songs for Frizzell. Lefty was so impressed he refused to go on-stage until Haggard was allowed to sing a song. Merle went out and sang a few songs to an enthusiastic response from the audience.

The reception persuaded Haggard to actively pursue a musical career. While he was working during the day in oil fields and farms, he performed at local Bakersfield clubs. His performances led to a spot on a local television show, Chuck Wagon. In 1956, he married Leona Hobbs; the couple moved into his family's old converted boxcar. Throughout 1957, Haggard was plagued by financial problems, which made him turn to robbery. At the end of the year, he attempted to rob a restaurant along with two other burglars; the three were drunk at the time. Believing it was three o'clock in the morning, the trio tried to open up the back door of the restaurant. However, it was 10:30 and the establishment was still open. Although the trio fled the scene, Haggard was arrested that day. The following day, he escaped from prison in order to make peace with his wife and family; later that day, he was recaptured. Haggard was sentenced to a 15-year term and sent to San Quentin prison.

Prison didn't immediately lead Merle into rehabilitation. He was fired from a series of prison jobs and planned an escape from the jail, but was talked out of it by fellow inmates. Nearly two years into his sentence, Haggard discovered that his wife was pregnant with another man's child. The news sent Haggard over the edge. Soon, he and his cellmate began a gambling racket and brewing beer in their cell. Before long, Haggard was caught drunk and was placed in isolation for a week. During his time in isolation, he had several conversations with Caryl Chessman, an author and a member of death row. The conversations and the time in isolation convinced Haggard to turn his life around. After he left isolation, he began working in the prison's textile plant and took some high-school equivalency courses; he was also allowed to play in the prison's country band. At his second parole hearing in 1960, Haggard was given a five-year sentence -- two years and nine months in jail, two years and three months on parole; he left prison 90 days later.

Merle moved back in with Leona and returned to manual labor. In the meantime, he sang at local clubs at night. After taking second place at a local talent contest, Haggard was asked to become a relief singer for a band led by Johnny Barnett at one of the most popular Bakersfield clubs, Lucky Spot. Soon, Merle was making enough money playing music that he could quit his ditch-digging job. While singing with Barnett, he gained the attention of Fuzzy Owen, who owned the small record label Tally Records. Owen and his cousin Lewis Talley were instrumental in establishing Haggard's musical career. Owen made the first recording of Haggard, cutting a demo version of one of the singer's first songs, "Skid Row." Shortly after the recording, Haggard called Talley, who had praised him earlier in his career. Talley was able to land Haggard a job at Paul's Cocktail Lounge, which led to a slot on a local music television show.

During this time, Bakersfield country was beginning to become a national scene, largely due to the hit singles of Buck Owens. At a time when mainstream country was dominated by the lush, smooth countrypolitain sound of Nashville, Bakersfield country grew out of hardcore honky tonk, adding elements of Western swing. Bakersfield country also relied on electric instruments and amplification more than other subgenres of country, giving the music a hard, driving, edgy flavor. During the late '50s, Tommy Collins and Wynn Stewart were two of the Bakersfield artists to have hits, and both were influential on Haggard's career, musically as well as professionally. Haggard had admired Stewart's vocal style, and it helped shape his phrasing.

Early in 1962, Haggard traveled to Las Vegas to see Wynn Stewart's club show. Stewart was not at the club, having left to find a replacement bass player. During the show, one of Stewart's guitarists remembered Haggard and invited him to sing a couple of songs on-stage. Stewart walked in while Haggard was singing and was impressed, asking him to join his band as a bassist. For six months in 1962 and 1963, Merle performed with Stewart's band. During this time, Haggard heard Wynn's song "Sing a Sad Song" and asked the star if he could record it. Stewart gave him the song and Merle recorded it for Tally Records in 1963. Although Tally had minimal distribution, the record became a national hit, climbing to number 19 on the country charts early in 1964.

"Sam Hill," Haggard's second single, wasn't as successful, but a duet with Bonnie Owens, the former wife of Buck Owens, called "Just Between the Two of Us," broke into the Top 40. The next year, his version of Liz Anderson's "(My Friends Are Gonna Be) Strangers" broke him into the Top Ten and established him as a budding star. Capitol Records bought out his contract with Tally and Merle released "I'm Gonna Break Every Heart I Can," his first single for Capitol, in the fall of 1965. The single wasn't a success, scratching into the Top 50, but his next single, "Swinging Doors," was a smash hit, rocketing to number five in the spring of 1966. Late in 1965, Haggard began recruiting a backing band and named them the Strangers.

Haggard became a genuine country superstar in 1966, with three Top Ten hits, including "Swinging Doors." "The Bottle Let Me Down" climbed to number three and "The Fugitive" (later retitled "I'm a Lonesome Fugitive") became his first number one. He was voted the Top Male Vocalist by the Academy of Country Music Awards, while he and Bonnie were named the Top Vocal Group for the second year in a row.

Haggard's songwriting was beginning to blossom and audiences embraced his music, sending his "I Threw Away the Rose" to number three early in 1967, beginning a remarkable streak of 37 straight Top Ten hits, including 23 number one singles. "I Threw Away the Rose" was followed by four straight number one hits -- "Branded Man," "Sing Me Back Home," "The Legend of Bonnie and Clyde," and "Mama Tried," which was heard in Killers Three, a movie that featured Haggard's debut as an actor. With the exception of "Bonnie and Clyde," the songs represented a change in Haggard's songwriting, as he began to directly address his troubled history. By 1970, he was talking about his time in San Quentin in the press, yet these songs represented the first time he had mentioned his past directly. Each single was a bigger hit than the previous song, which encouraged Haggard to continue writing in a more personal style.

Throughout 1968, Haggard's star continued to rise, with two number one hits ("Bonnie and Clyde," "Mama Tried") and the number three "I Take a Lot of Pride in What I Am," as well as four albums. Later that year, he recorded his first conceptual album, Same Train, Different Time. Released in early 1969, the record was not only an affectionate salute to one of Haggard's heroes, it reflected a fascination with American history and a desire to expand his music by adding stronger elements of Western swing, jazz, and blues.

Merle released three singles in 1969 -- "Hungry Eyes," "Workin' Man Blues," and "Okie from Muskogee" -- and all three reached number one. In particular, "Okie from Muskogee" sparked a tremendous amount of attention. An attack on the liberal hippies who represented American pop culture in the late '60s, the song struck a chord in audiences across the country, just missing the pop Top 40. Because of the song, Haggard was asked to endorse George Wallace, but he refused. "Okie from Muskogee" cemented the singer's stardom, and he won a large amount of awards in 1969 and 1970. In both years, he was named the Top Male Vocalist by the ACM and the Strangers were voted the best band, while the new Country Music Association voted him Entertainer of the Year and Top Male Vocalist in 1970.

Haggard released a sequel to "Okie" called "The Fightin' Side of Me" at the beginning of 1970, and it also shot to number one. That year, he released A Tribute to the Best Damn Fiddle Player in the World (Or My Salute to Bob Wills), which helped spark a revival of Western swing in the '70s. Throughout 1971 and 1972, the hits kept coming, including "Soldier's Last Letter," "Someday We'll Look Back," "Daddy Frank (The Guitar Man)," "Carolyn," "Grandma Harp," "It's Not Love (But It's Not Bad)," and "I Wonder If They Ever Think of Me." In 1972, the governor of California, Ronald Reagan, granted Haggard a full pardon. The following year, his hit streak continued, and he scored his biggest hit, "If We Make It Through December," which peaked at number 28 on the pop charts. As his reign on the top of the country charts continued in 1974, he played on Bob Wills' last album, For the Last Time. Wills died in 1975, leaving Merle his fiddle.

Haggard stayed with Capitol Records until 1977, and never once did his grip on the American audience slip during his tenure there. During his time on MCA afterward, he continued to have a number of hits, but his work was becoming slightly inconsistent. His first two singles for the record label, "If We're Not Back in Love by Monday" and "Ramblin' Fever," hit number two and he continued to have hits with the label throughout the end of the decade and the first part of the '80s. "I'm Always on a Mountain When I Fall" and "It's Been a Great Afternoon" were number two hits in 1978. In 1979, he only had two hits, while in 1980, two selections from the Clint Eastwood movie Bronco Billy reached the Top Three, "The Way I Am" and "Misery and Gin"; Haggard also appeared in the film. The two hits paved the way for his two biggest singles with MCA, the number one duet with Eastwood "Bar Room Buddies" and the number one "I Think I'll Just Stay Here and Drink." Early in 1981, Haggard had a Top Ten hit with "Leonard," a tribute to his old friend Tommy Collins.

Later that year, Haggard published his autobiography, Sing Me Back Home; he also left MCA and signed with Epic Records. Once at Epic, he began producing his own records, which gave the music a leaner sound. His first two singles for the label, "My Favorite Memory" and "Big City," were number one hits. The following year, he released a duet album with George Jones called A Taste of Yesterday's Wine, which featured the number one single "Yesterday's Wine" and the Top Ten "C.C. Waterback." From 1983 until the beginning of 1985, Haggard continued to score number one hits, including the number one duet with Willie Nelson "Pancho and Lefty."

Merle's chart fortunes began to change in 1985 as a new breed of singers began to dominate the chart. Nearly every one of the artists, from George Strait to Randy Travis, was greatly influenced by Haggard, but their idol's new singles now had a tough time reaching the top of the charts. He had two Top Ten hits in 1986, and 1987's Chill Factor was a success, spawning the Top Ten title track and "Twinkle, Twinkle Lucky Star," which would prove to be his last number one hit. In 1990, he signed with Curb Records, but he continued to have trouble reaching the charts; 1994 spawned his last modest hit, "In My Next Life," which reached the Top 60.

When his contract with Curb ran out, Haggard, hoping for better promotion and greater artistic freedom, signed with Anti, a subsidiary of the Epitaph punk-pop label. His first effort for Anti was released in late 2000; titled If I Could Only Fly, the gentle acoustic album was greeted with strong reviews. Haggard released one more album for Anti, 2001's Roots, Vol. 1, before departing. After 2003's Like Never Before, Haggard returned to his old home, EMI, the following year, releasing a collection of American pop standards called Unforgettable at the end of that year. Chicago Wind appeared in the summer of 2005. Haggard then turned to bluegrass, releasing the appropriately titled The Bluegrass Sessions, which featured appearances by Marty Stuart, Aubrey Haynie, and Alison Krauss (among others) in 2007. In 2008 he got the Bear Family treatment with the release of the multi-disc box sets Hag: The Studio Recordings 1969-1976 and Hag: Concepts, Live & the Strangers: The Capitol Recordings 1968-1976. I Am What I Am, an album of new songs, appeared from Vanguard Records in 2010. A second Vanguard album, Working in Tennessee, co-produced by Haggard with Lou Bradley at Haggard's own northern California studio, appeared the following year in 2011. Four years later, Haggard teamed up with his old friend Willie Nelson for Django and Jimmie, their first collaboration in 20 years. Preceded by the single "It's All Going to Pot," the album debuted at number one on the Billboard country chart upon its June 2015 release. Less than a year later, exactly on his 79th birthday (April 6, 2016), Haggard died of complications from pneumonia at his home in Palo Cedro, California.

Even when success eluded him, Merle Haggard's music remained some of the most consistently interesting and inventive in country music. Not only have his recordings remained fresh, but each subsequent generation of country singers shows a great debt to his work. That fact stands as a testament to his great talent even more than his induction into the Country Music Hall of Fame. ~ Stephen Thomas Erlewine

As a songwriter and performer, Willie Nelson has played a vital role in post-rock & roll country music. Although he didn't become a star until the mid-'70s, he spent the 1960s writing songs that became hits for stars like Ray Price ("Night Life"), Patsy Cline ("Crazy"), Faron Young ("Hello Walls"), and Billy Walker ("Funny How Time Slips Away"), as well as releasing a series of records on Liberty and RCA that earned him a small but devoted cult following. During the early '70s, Willie abandoned Nashville for his native Texas, setting up shop with the redneck hippies in Austin and taking control of his music on the landmark Shotgun Willie (1973) and Phases & Stages (1974). Nelson found a kindred spirit in Waylon Jennings and, together, they spearheaded the outlaw country movement that finally made him a star by 1975. Following the crossover success of that year's Red Headed Stranger and "Blue Eyes Crying in the Rain," Nelson became a genuine success, as recognizable in pop circles as he was to country audiences; in addition to recording, he also launched an acting career in the early '80s. Even when he was a star, he never played it safe musically. Instead, he borrowed from a wide variety of styles, including traditional pop -- his biggest album was 1978's Stardust, a collection of interpretations of the Great American Songbook -- Western swing, jazz, traditional country, cowboy songs, honky tonk, rock & roll, folk, and the blues, creating a distinctive, elastic hybrid. Nelson remained at the top of the country charts until the mid-'80s, when his lifestyle -- which had always been close to the outlaw clichés with which his music flirted -- began to spiral out of control, culminating in an infamous battle with the IRS in the late '80s. Nelson's hit singles dried up by the early '90s, but he kept performing and recording at a prodigious pace, both on his own and in a variety of collaborative settings, including the country supergroup the Highwaymen. Occasionally, one of Willie's albums would garner attention from a wider audience, such as 1993's Don Was-produced Across the Borderline or 1998's Teatro, but by the 2000s, he was a beloved figure in American pop culture, embraced for his music, humor, and hippie lifestyle. Nelson wasn't one to rest on his laurels, either. During the 2010s, he struck up a fruitful collaboration with producer Buddy Cannon, who helmed a series of relaxed, mortality-minded albums over the next decade, a string that culminated in 2022's A Beautiful Time.

Nelson began performing music as a child growing up in Abbott, Texas. After his father died and his mother ran away, Nelson and his sister Bobbie were raised by their grandparents, who encouraged both children to play instruments. Willie picked up the guitar, and by the time he was seven, he was already writing songs. Bobbie learned to play piano, eventually meeting -- and later marrying -- fiddler Bud Fletcher, who invited both of the siblings to join his band. Nelson had already played with Raychecks' Polka Band, but with Fletcher, he acted as the group's frontman. Willie stayed with Fletcher throughout high school. Upon his graduation, he joined the Air Force but had to leave shortly afterward when he became plagued by back problems. Following his disenrollment from the service, he began looking for full-time work.

After working several part-time jobs, he landed one as a country DJ at Fort Worth's KCNC in 1954. Nelson continued to sing in honky tonks as he worked as a DJ, deciding to make a stab at recording career by 1956. That year, he headed to Vancouver, Washington, where he recorded Leon Payne's "Lumberjack." At that time, Payne was a DJ and he plugged "Lumberjack" on the air, which eventually resulted in sales of 3,000 -- a respectable figure for an independent single, but not enough to gain much attention. For the next few years, Nelson continued to DJ and sing in clubs. During this time, he sold "Family Bible" to a guitar instructor for 50 dollars, and when the song became a hit for Claude Gray in 1960, Nelson decided to move to Nashville the following year to try his luck. Though his nasal voice and jazzy, off-center phrasing didn't win him many friends -- several demos were made and then rejected by various labels -- his songwriting ability didn't go unnoticed, and soon Hank Cochran helped Willie land a publishing contract at Pamper Music. Ray Price, who co-owned Pamper, recorded Nelson's "Night Life" and invited him to join his touring band, the Cherokee Cowboys, as a bassist.

Arriving at the beginning of 1961, Price's invitation began a watershed year for Nelson. Not only did he play with Price -- eventually taking members of the Cherokee Cowboys to form his own touring band -- but his songs also provided major hits for several other artists. Faron Young took "Hello Walls" to number one for nine weeks, Billy Walker made "Funny How Time Slips Away" into a Top 40 country smash, and Patsy Cline made "Crazy" into a Top Ten pop crossover hit. Earlier in the year, he signed a contract with Liberty Records and began releasing a series of singles that were usually drenched in strings. "Willingly," a duet with his then-wife Shirley Collie, became a Top Ten hit for Nelson early in 1962, and it was followed by another Top Ten single, "Touch Me," later that year. Both singles made it seem like Nelson was primed to become a star, but his career stalled just as quickly as it had taken off, and he was soon charting in the lower regions of the Top 40. Liberty closed its country division in 1964, the same year Roy Orbison had a hit with "Pretty Paper."

When the Monument recordings failed to become hits, Nelson moved to RCA Records in 1965, the same year he became a member of the Grand Ole Opry. Over the next seven years, he had a steady stream of minor hits, highlighted by the number 13 hit "Bring Me Sunshine" in 1969. Toward the end of his stint with RCA, he had grown frustrated with the label, which had continually tried to shoehorn him into the heavily produced Nashville sound. By 1972, he wasn't even able to reach the country Top 40. Discouraged by his lack of success, Nelson decided to retire from country music, moving back to Austin, Texas, after a brief and disastrous sojourn into pig farming. Once he arrived in Austin, Nelson realized that many young rock fans were listening to country music along with the traditional honky tonk audience. Spotting an opportunity, Nelson began performing again, scrapping his pop-oriented Nashville sound and image for a rock- and folk-influenced redneck outlaw image. Soon, he earned a contract with Atlantic.

Shotgun Willie (1973), Nelson's first album for Atlantic, was evidence of the shift of his musical style, and although it initially didn't sell well, it earned good reviews and cultivated a dedicated cult following. By the fall of 1973, his version of Bob Wills' "Stay All Night (Stay a Little Longer)" had cracked the country Top 40. The following year, he delivered the concept album Phases and Stages, which increased his following even more with the hit singles "Bloody Mary Morning" and "After the Fire Is Gone." But the real commercial breakthrough didn't arrive until 1975, when he severed ties with Atlantic and signed to Columbia Records, which gave him complete creative control of his records. Nelson's first effort for Columbia, The Red Headed Stranger, was a spare concept album about a preacher, featuring only his guitar and his sister's piano. The label was reluctant to release it with such stark arrangements, but they relented and it became a huge hit, thanks to Nelson's understated cover of Roy Acuff's "Blue Eyes Crying in the Rain."

Following the breakthrough success of The Red Headed Stranger, as well as Waylon Jennings' simultaneous success, outlaw country -- so named because it worked outside of the confines of the Nashville industry -- became a sensation, and RCA compiled the various-artists album Wanted: The Outlaws!, using material Nelson, Jennings, Tompall Glaser, and Jessi Colter had previously recorded for the label. The compilation boasted a number one single in the form of the newly recorded Jennings and Nelson duet "Good Hearted Woman," which was also named the Country Music Association's single of the year. For the next five years, Nelson consistently charted on both the country and pop charts, with "Remember Me," "If You've Got the Money I've Got the Time," and "Uncloudy Day" becoming Top Ten country singles in 1976; "I Love You a Thousand Ways" and the Mary Kay Place duet "Something to Brag About" were Top Ten country singles the following year.

Nelson enjoyed his most successful year to date in 1978, as he charted with two very dissimilar albums. Waylon and Willie, his first duet album with Jennings, was a major success early in the year, spawning the signature song "Mammas Don't Let Your Babies Grow Up to Be Cowboys." Later in the year, he released Stardust, a string-augmented collection of pop standards produced by Booker T. Jones. Most observers believed that the unconventional album would derail Nelson's career, but it unexpectedly became one of the most successful records in his catalog, spending almost ten years in the country charts and eventually selling over four million copies. After the success of Stardust, Willie branched out into film, appearing in the Robert Redford movie The Electric Horseman in 1979 and starring in Honeysuckle Rose the following year. The latter spawned the hit "On the Road Again," which became another one of Nelson's signature songs.

Nelson continued to have hits throughout the early '80s, when he had a major crossover success in 1982 with a cover of Elvis Presley's hit "Always on My Mind." The single spent two weeks at number one and crossed over to number five on the pop charts, sending the album of the same name to number two on the pop charts as well as quadruple-platinum status. Over the next two years, he had hit duet albums with Merle Haggard (1983's Poncho & Lefty) and Jennings (1982's WWII and 1983's Take It to the Limit), while "To All the Girls I've Loved Before," a duet with Latin pop star Julio Iglesias, became another major crossover success in 1984, peaking at number five on the pop charts and number one on the country singles chart.

Following a string of number one singles in early 1985, including "Highwayman," the first single from the Highwaymen, a supergroup he formed with Jennings, Johnny Cash, and Kris Kristofferson, Nelson's popularity gradually began to erode. A new generation of artists had captured the attention of the country audience, which began to drastically cut into his own audience. For the remainder of the decade, he recorded less frequently and remained on the road; he also continued to do charity work, most notably Farm Aid, an annual concert that he founded in 1985 designed to provide aid to ailing farmers. While his career was declining, an old demon began to creep up on him: the IRS. In November 1990, Nelson was given a bill for $16.7 million in back taxes. During the following year, almost all of his assets -- including several houses, studios, farms, and various properties -- were taken away, and to help pay his bill, he released the double album The IRS Tapes: Who'll Buy My Memories? Originally released as two separate albums, the records were marketed through television commercials, and all the profits were directed to the IRS. By 1993 -- the year he turned 60 -- his debts had been paid off, and he relaunched his recording career with Across the Borderline, an ambitious album produced by Don Was and featuring cameos by Bob Dylan, Bonnie Raitt, Paul Simon, Sinéad O'Connor, David Crosby, and Kris Kristofferson. The record received strong reviews and became his first solo album to appear in the pop charts since 1985.

After the release of Across the Borderline, Nelson continued to work steadily, releasing at least one album a year and touring constantly. In 1993, he was inducted into the Country Music Hall of Fame, but by that time, he had already become a living legend for all country music fans across the world. Signing to Island for 1996's Spirit, he resurfaced two years later with the critically acclaimed Teatro, produced by Daniel Lanois. Nelson followed up that success with the instrumental-oriented Night and Day a year later; Me and the Drummer and Milk Cow Blues followed in 2000. The Rainbow Connection, which featured an eclectic selection of old-time country favorites, appeared in spring 2001.

Amazingly prolific as a recording artist, Nelson released The Great Divide on Universal in 2002. A collection of his early-'60s publishing demos for Pamper Music called Crazy: The Demo Sessions came out on Sugar Hill in 2003. Later that year, Nelson released Run That by Me One More Time, which reunited him with Ray Price and kicked off a relationship with Lost Highway Records. It Always Will Be and Outlaws and Angels both appeared on Lost Highway in 2004, followed by the release of Nelson's long-delayed attempt at a country-reggae fusion, Countryman, also on Lost Highway, in 2005. You Don't Know Me: The Songs of Cindy Walker arrived the following year, along with Songbird, Nelson's collaboration with alt-country singer/songwriter Ryan Adams and his band the Cardinals. The double-disc Last of the Breed, an ambitious project that paired Nelson with Merle Haggard, Ray Price, and Asleep at the Wheel, was released by Lost Highway in 2007, followed by the Kenny Chesney/Buddy Cannon-produced Moment of Forever a year later in 2008.

Also in 2008, Nelson paired with jazz trumpeter Wynton Marsalis for the live album Two Men with the Blues, and with harmonica player and producer Mickey Raphael for some serious-repair remixes of vintage Nelson releases from RCA originally recorded between 1966 and 1970 called Naked Willie. Lost Highway, an album of duets with country and pop singers ranging from Shania Twain to Elvis Costello, appeared in 2009. Also appearing in 2009 was the jazz-inflected American Classic from Blue Note. Country Music followed next from Rounder in 2010. Nelson reunited with Marsalis again for 2011's Here We Go Again: Celebrating the Genius of Ray Charles, which was recorded live on February 9 and 10, 2009, at the Rose Theater with Norah Jones also on board. A CD drawn from the shows appeared on Blue Note in the spring of 2011 and in the fall, Willie released a covers collection called Remember Me, Vol. 1. He then signed with Sony Legacy and released Heroes in the summer of 2012, following it in the spring of the next year with a collection of standards called Let's Face the Music and Dance. That fall, he released To All the Girls..., a collection of new duets with female singers.

Nelson kept to a rigorous touring schedule despite the fact that he turned 80 in 2013. Though he'd been recording mostly covers for well over a decade, Nelson re-engaged as a songwriter while traveling. Band of Brothers, issued in June 2014, featured nine originals (co-written with producer Buddy Cannon) among its 14 new songs. Six months later, Nelson launched a projected series of albums (given the collective name Willie's Stash, devoted to music especially close to his heart) with December Day, a low-key collaboration with his sister Bobbie Nelson, in which they performed a set of old standards and lesser-known tunes from Nelson's songbook. In 2015, Nelson teamed up with his old friend Merle Haggard for Django and Jimmie, their first collaboration in 20 years. Preceded by the single "It's All Going to Pot," the album debuted at number one on the Billboard country chart upon its June 2015 release. Early in 2016, Nelson issued Summertime: Willie Nelson Sings Gershwin, and later that year he saluted his early inspiration, Ray Price, with For the Good Times: A Tribute to Ray Price.

Nelson returned to original songs in April 2017 with the album God's Problem Child, which was once again co-produced by Buddy Cannon. Later that October, Nelson released the second volume in the Willie's Stash series: Willie Nelson and the Boys, a collection of classic country covers recorded with his sons Lukas and Micah. That same month, Light in the Attic issued two catalog projects by Nelson. Teatro: The Complete Sessions, produced by Daniel Lanois, included seven previously unreleased tracks and a DVD of director Wim Wenders' documentary of the live sessions for the album, which took place in a picturesque vintage movie theater. The latter volume was a Record Store Day reissue of the more somber 1996 Island Records' release of Spirit on gold vinyl. Undercelebrated at the time of its release, it has become among the most treasured outings of his late career, featuring the legendary fiddler Johnny Gimble among its personnel.

In April 2018, Nelson and Cannon were back with another studio album, Last Man Standing, which included the single "Me and You." The set debuted at number three on the Billboard Top Country Albums chart. Five months later, Nelson released My Way, a tribute to Frank Sinatra; it took home the Grammy for Best Traditional Pop Vocal Album in 2019. He issued his next studio LP, Ride Me Back Home, in June 2019. Its tracks were a mix of new material, co-written by Nelson and Cannon, and covers of songs from Mac Davis, Billy Joel, and others. The title track was co-written by Sonny Throckmorton and was the first single issued from the album; it went on to win the Grammy for Best Country Solo Performance. Nelson followed Ride Me Back Home with the mellow and elegiac First Rose of Spring, which relied primarily on covers, including versions of Toby Keith's "Don't Let the Old Man In" and Johnny Paycheck's "I'm the Only Hell My Mama Ever Raised." The record debuted at number five on Billboard's Country Albums chart and number 49 on its Top 200.

Nelson released the Grammy-nominated That's Life, his second album of Frank Sinatra covers, in February 2021. Later that year, he issued The Willie Nelson Family, a collection of spiritual tunes recorded with such family members as his sister Bobbie, his daughters Amy and Paula, and his sons Lukas and Micah, who both play in Promise of the Real.

Nelson's sister Bobbie died on March 10, 2022, roughly a month and a half before Willie released A Beautiful Time, another collaboration with Buddy Cannon. The album found Nelson addressing his mortality on such original tunes as "I Don't Go to Funerals" and "Live Every Day," and it also featured covers of the Beatles' "With a Little Help from My Friends" and Leonard Cohen's "Tower of Song." A Beautiful Time won the Grammy Award for Best Country Album in 2023, the same year Nelson won a trophy for Best Country Solo Performance for "Live Forever," a cut from the Billy Joe Shaver tribute album of the same name. Nelson saluted the great country songwriter Harlan Howard with I Don't Know a Thing About Love: The Songs of Harlan Howard, which appeared in March 2023.

Five months later, Nelson delivered Bluegrass, in which he played several selections from his songbook in a bluegrass style aided by such musicians as Dan Tyminski, Rob Ickes, and Aubrey Haynie. It was the first album where Nelson didn't play his signature guitar Trigger since he acquired the instrument in 1969. At the end of the year, Nelson released Long Story Short: Willie Nelson 90, a CD/Blu-Ray documenting his celebratory birthday concerts at the Hollywood Bowl in April 2023. ~ Stephen Thomas Erlewine & Steve Leggett