Oct 302023

In the Spotlight showcases a cross-section of an artist’s cover work. View past installments, then post suggestions for future picks in the comments!

Back in 2021, Cover Me compiled a list of the top 30 Willie Nelson covers of all time. A comprehensive list, it included covers of many of Nelson’s trademark songs such as “Crazy” and “Funny How Time Slips Away.” Even then we noted we were leaving out a key component of the story: the number of covers Nelson has recorded himself.

As of this writing, Secondhandsongs.com lists a whopping 991 covers. Granted it counts instances where he re-recorded new versions of his old cover songs with other people. For example: it lists every single duet of “Baby It’s Cold Outside.” Nelson’s catalog of covers is both extensive and exceptional. One could easily place many of his covers, such as “Always On My Mind,” “Stardust,” or “Blue Eyes Crying in the Rain,” among the best of all time.

In 2023, Nelson has hit two major milestones – he turned 90 in April. and in November he’ll be inducted into the Rock & Roll Hall of Fame – so we decided to revisit his covers collection.

For this particular list I decided to go by Rock N’ Roll Hall of Fame rules, which stipulate that artists are eligible to be inducted 25 years after their first commercial release. While Nelson released his first album in 1962, I only included covers he recorded or released after 1998. For most artists in the Rock Hall this would be a pretty weak selection. For Nelson, it gives a new definition to the expression “late career renaissance.” Since 1998 he has, according to Allmusic.com, released 51 studio and live albums, including a new album, Bluegrass, on Sept. 15 of this year. These releases over the years have included countless cover songs.

In his later years, Nelson has become an ideal artist for the streaming era. He releases new music the same way TikTok influencers put out videos. He drops two, sometimes three albums a year, along with many singles. In fact, it seems like every time I click on Spotify there’s something new from him. Without the burden of buying an album, one can listen to his new records, discover the new favorites, add them to a playlist, and wait (usually not long) for the next album or single to drop.

Though Nelson is first and foremost a country singer, he is also a natural choice for the Rock Hall. There isn’t a single alt-country rocker with long hair, a mullet or a beard who doesn’t owe some debt of gratitude, or at least some degree of influence, to the music and style of the Red Headed Stranger. As his music from the last two and a half decades shows, he has no problem shifting from genre to genre: whether it’s country, rock, R&B, or Big Band jazz, it all feels like pure Willie. To honor Nelson’s introduction into the Rock & Roll Hall of Fame, here’s a list of extraordinary covers he’s released in the last 25 years presented chronologically.

Note: Given the depth of his work during this timespan, I’m bound to have missed some gems, so please include your favorites from 1998-2023 in the comments below.

Willie Nelson – Rainbow Connection (Kermit the Frog cover)

“Rainbow Connection” is the classic Oscar-nominated song from The Muppet Movie, famous for its easy-to-sing, heartwarming chorus, as well as Kermit the Frog’s banjo playing. In his 2001 rendition, Nelson dropped the orchestration (and the banjo) and played it as a quiet cover. The track still carries the emotional heft of the original, but in Nelson’s signature, laid-back style.

Willie Nelson – Time After Time (Cyndi Lauper cover)

In 2002, Nelson released The Great Divide, a more radio-friendly album. It included collaborations with Rob Thomas and duets with Lee Ann Womack, Kid Rock, Sheryl Crow and Brian McKnight. Critics savaged the album, accusing Nelson of trying to be, well, contemporary. Two decades later some of the tracks have weathered better than critics’ disdain, including this cover of Cyndi Lauper’s “Time After Time.” Nelson combines fast-paced acoustic picking and hard-rocking electric guitar. Now it could almost be described as retro.

Willie Nelson – Cherokee Maiden (Bob Wills and His Texas Playboys cover)

Cindy Walker was a Texas born songwriter known for penning many hits “You Don’t Know Me,” and “Dream Baby (How Long Must I Dream).” Nelson’s 2006 tribute album You Don’t Know Me: The Songs of Cindy Walker contained this cover of “Cherokee Maiden.” A huge hit for Bob Wills and His Texas Playboys in the ‘40s, Nelson delivers the track as a spot-on Western-swing style cover. The track showcases his abilities to sing country music from all generations.

Willie Nelson – Stella Blue (Grateful Dead cover)

Throughout his career, Nelson has always been very open about the importance of collaborating with other great artists, and on this track the approach leads to near perfection. The late Neal Casal never became a superstar, but he was a well known musician in the jamband and alt-country music scenes. While serving as a guitarist/pianist for Ryan Adams and the Cardinals, he backed Nelson on the 2006 album Songbird. It was here Casal contributed some of his finest work on a cover of the Grateful Dead’s “Stella Blue.” The combination of Nelson’s gut-wrenching singing and Casal’s inspired post-psychedelic guitar playing earned the track a spot on our list of greatest all time Dead covers. It’s easily one of Nelson’s best, too.

Willie Nelson – Gotta Serve Somebody (Bob Dylan cover)

Funky is not a word I often associate with Willie Nelson. But the adjective best describes his cover of Bob Dylan’s “Gotta Serve Somebody.” The eight-minute track feels more like a song you would hear on a classic R&B station than anything on a country station, let alone a Willie Nelson deep cut from 2008.

Willie Nelson and Wynton Marsalis – Stardust (Hoagy Carmichael cover)

Yes, I know Willie Nelson first released his cover of “Stardust”on the classic 1978 standards album of the same name. Those familiar with Nelson’s career know that he’s never afraid to revisit a classic. He did just that on the 2008 live album Two Men with the Blues, which he recorded with trumpeter Wynton Marsalis. Backed by a virtuosic jazz combo, Nelson recaptures the honest delivery of his earlier recording, while Marsalis delivers a stunning trumpet solo. As you’ll see below, it’s no surprise these two wanted to record together again.

Willie Nelson and Asleep at the Wheel – I’m Sittin’ On Top of the World (Mississippi Sheiks cover)

The 2009 album Willie and the Wheel is a collaboration between Nelson and the long-running retro-country act Asleep at the Wheel. One of the highlights is this rendition of “I’m Sittin’ On Top of the World.” It’s one of those great standards that’s been performed by countless country and blues singers from Bill Monroe to Howlin’ Wolf. Nelson channels both sides of the musical equation. Like the album as a whole, his cover contains elements of blues guitar and bass, with heavy amounts of fiddle, some horns, all held together by a slow swinging beat.

Willie Nelson, Wynton Marsalis and Norah Jones – What I’d Say (Ray Charles cover)

Willie Nelson and Ray Charles had a deep musical legacy that spanned the decades. In 1984, the two had a hit with “Seven Spanish Angels.” Then in 2004 they teamed up for a duet of “It Was a Very Good Year.” In 2011, Nelson joined Norah Jones, Wynton Marsalis and the Jazz at Lincoln Center Orchestra for this rollicking Charles tribute album. With so much musical firepower on stage, it’s no surprise that so many of the cuts are fantastic. This spirited take of “What I’d Say” is the standout. Like Charles’ original, the cover combines elements of blues, jazz, gospel and R&B, making you want to dance, clap and sing along.

Willie Nelson and Merle Haggard – Don’t Think Twice, It’s Alright (Bob Dylan cover)

Willie Nelson and Merle Haggard recorded multiple albums together. In 2015, several months before Haggard’s death, the two released one final duets album Django and Jimmie. What’s striking about this cover of the well-worn Bob Dylan classic “Don’t Think Twice, It’s Alright” is how comfortable the two sound singing together. Rather than a breakup song, as the two trade Dylan’s barbs, they have the feel of an old couple having a disagreement from which they’ll quickly make up.

Willie Nelson – Blue Moon (Rodgers and Hart cover)

Nelson released My Way in 2018. It was billed as a tribute to Frank Sinatra, but really it’s just a solid collection of standards, backed with big-band style arrangements. Case in point: his cover of “Blue Moon.” Though recorded by Sinatra, “Blue Moon” was originally penned by Broadway tunesmiths Richard Rodgers and Lorenz Hart in the 1930s. Nelson plays it as a mid-tempo piece of lounge jazz more fitting for a New York jazz club than a honky tonk.

Willie Nelson – Luck Be A Lady (Guys and Dolls cover)

Not content to record one Frank Sinatra tribute album while in his 80s, Nelson released That’s Life in 2021, another album of Sinatra (aka Great American Songbook) covers. Like My Way, the album features Nelson singing big-band style versions of many standards. Among the standouts is this version of “Luck Be A Lady,” a song popularized by the musical Guys and Dolls. Nelson’s cover veers into Latin jazz territory, making it one of the more unique covers on the album.

Willie Nelson and Family – I Saw the Light (Hank Williams cover)

Nelson has recorded and toured with many of his children and siblings over the years. In 2021, he released The Willie Nelson Family, an album featuring various family members. The album has the feel of a relaxed summer church picnic as it includes covers of secular and spiritual hymns from “Keep on the Sunny Side” to George Harrison’s “All Things Must Pass.” The family presents Hank Williams’ come-to-Jesus classic “I Saw the Light” as a sing-along. It’s enough to capture the hearts and minds of saints and sinners alike.

Willie Nelson – With A Little Help from My Friends (The Beatles cover)

“With a Little Help from My Friends” was the second song on the Beatles’ masterwork Sgt. Pepper’s Lonely Hearts Club Band. It eventually became one of the most enduring tracks of the ‘60s thanks in part to Joe Cocker’s scorching cover. Nelson’s cover from the 2022 album A Beautiful Times little resembles those versions. Instead, he plays it as a harmonica-powered alt-country rock tune. The track could have fit well on any of Nelson’s outlaw country records from the last five decades.

Willie Nelson – Tiger By The Tail (Buck Owens cover)

In the early ‘60s, when Nelson was just starting to make his name in Nashville, Buck Owens was one of the biggest stars in country music. The singer/guitarist led a movement known as the Bakersfield sound, a fusion of country, rock and rockabilly, featuring hyper-fast guitar licks. In 2023, Nelson recorded a tribute album in honor of Harlan Howard, a songwriter who penned several hits for Owens. Nelson opened the album with this rendition of “Tiger by the Tale,” which pays direct homage to Owens’ original 1964 hit. Like many of Nelson’s songs, it’s both retro and contemporary, channeling past legends while showing himself just as powerful an artist in 2023 as he was at any point in his career.

Check out our complete series paying tribute to every 2023 Rock and Roll Hall of Fame inductee in covers!

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