Country collaborations through the years

Classified a country tune by Billboard, this jaunty number was the result of a famous pairing of two artists who weren’t considered country artists by any stretch of the imagination. Famous crooner/movie star Bing Crosby and the famed Andrews Sisters teamed up to record this 1943 song by Al Dexter, which topped the Juke Box Folk Records chart (later to be named the Hot Country Songs chart) and became part of the WWII era’s most popular tunes. 

This husband-and-wife musical pair saw famed guitarist Les Paul (he of the famous line of electric guitars that bear his name) and vocalist Mary Ford record sixteen top-10 hits between 1950 and 1954. Paul, who pioneered jazz, country, and blues guitar, also was a visionary when it came to multitrack recording, which allowed him and Ford to record a number of songs that layered Paul’s guitar melodies and Ford’s vocal harmonies and blend them to create wildly inventive music that was ahead of its time.

Dolly Parton had already found success as a songwriter prior to joining Porter Wagoner’s syndicated TV show, but hadn’t quite broken through as a singer. Exposure on Wagoner’s show changed that, and despite an initial frosty audience reception, endeared herself to both the crowd and Wagoner’s record label, RCA, who signed Parton to her first major deal. Success, again, was slow-going, but her 1973 smash hit “Jolene” saw her outgrow Wagoner’s tutelage; she would later pen and perform “I Will Always Love You” as a tribute to her former mentor.

Years before the formation of their supergroup (mentioned later in this list), these two outlaw country legends joined forces to cover Ed Bruce’s 1976 hit, a sobering ballad warning mothers not to allow their children to chase the romantic — but lonely — life of a cowboy. The duo kept the somber, introspective quality of the song intact while adding their own outlaw mentality and sound to it.

Two Country Music Hall of Fame inductees would already make this 1983 hit a powerhouse collaboration, but the production and songwriting by the Brothers Gibb (better known as the Bee Gees) take this to an entirely different level. Originally penned for Marvin Gaye in an R&B style, it was changed for Rogers’ album “Eyes That See In The Dark,” and its country-pop hybrid sound would take it to the top of the Billboard Hot 100 — making it a true crossover hit.

As Willie Nelson tells it, he;d overheard a singer on the radio by whom he was charmed, and upon inquiring of his wife as to who it was, he was informed it was Spanish singer Julio Iglesias. “Why haven’t I sung a duet with him?” Nelson exclaimed, and he set about making it happen, choosing this 1975 song by Hal David and Albert Hammond. The pairing paid off in huge ways for both men, giving Iglesias his biggest hit in the US and Canada, and Nelson his biggest European hit.

Johnny Cash, Willie Nelson, Waylon Jennings, and Kris Kristofferson were pioneers of the outlaw country genre, and their supergroup The Highwaymen remains one of country’s only examples of such concentrated superstardom. Formed in 1985, the four were already among country music’s elder statesmen, as well as longtime friends. With only three albums recorded in the decade between 1985 and 1995, the foursome performed, fought, and thrived with each other through the years until the deaths of Jennings and Cash in 2002 and 2003, respectively. 

Trisha Yearwood garnered numerous awards as well as critical acclaim after her 1991 debut, though the year would also see her marriage fall apart. She would bounce back in 1992 with her second, also critically acclaimed album “Hearts In Armor,” drawing from her own emotional conflict, and would meet the Eagles’ Don Henley after a performance on “The Tonight Show.” An impressed Henley was invited to record with her, and would make the trip to Nashville to provide backing vocals for this ballad of working class love turned sour.

If you’re going to have a U2 song without Bono on lead vocals, you could do much worse than having The Man In Black fill in. The song’s haunting lyrics, loaded with religious imagery, is appropriately epic, if muted, and Bono refused to sing it as he’d envisioned only Johnny Cash being right for the job. Upon request, Cash flew out to Dublin and recorded it with the group, and created one of the band’s lasting, most enduring songs.

Sting originally composed and recorded this song in 1996, though realized upon writing it that its lyrics gave it a country feel. A year later, he would invite Toby Keith to record it as a duet, and the song would hit No. 2 on the Hot Country Songs charts, giving Sting his first — and, to date, only — country hit, though Keith would still be a couple years from his own breakthrough. The two would also perform the song at the 1997 CMAs.

Shania Twain and the Backstreet Boys were each at the height of their fame in 1999, and as a big fan of the Boys (she admitted to playing their music in her tour bus before shows to get pumped up), she would invite them onto to her TV concert special in Miami. The two would trade stage time for hits before joining together in a medley, and it’s worth seeking out footage of on YouTube if only to catch a glimpse of the oversized suits, regrettable haircuts, and overall late ‘90s hangout vibe.

Modern Super Bowl halftime shows featuring headlining popular music acts really didn’t come about until 1991, and since then, country music stars have really only been featured in two different shows. The first, in 1994, was an all-country act featuring Clint Black, Tanya Tucker, Travis Tritt, and the Judds, but the second (and last) was a interesting mélange of Shania Twain, No Doubt, and Sting, which, aside from being very representative of early 2000s popular music, highlighted country’s upward trend towards becoming nearly indistinguishable from modern pop music.

The sentiment expressed in Alan Jackson’s 2003 hit would seem to jibe well with the man responsible for “Margaritaville,” and judging by its success on the charts, listeners agreed. Teased for weeks prior to Jackson releasing his “Greatest Hits Vol. II” with the promise of a “special guest,” Jackson’s secret managed to stay just that, a secret — something that almost certainly couldn’t happen today. Buffett’s laid-back, boozy charm complemented Jackson’s nicely, and the song (as well as the sentiment behind it) still holds up to this day.

The Coal Miner’s Daughter had been country music royalty for four decades before crossing paths with Jack White in the early aughts. After a meeting in Manhattan, White, a longtime admirer of Lynn (he dedicated The White Stripes album “White Blood Cells” to her in 2001), proposed that he produce Lynn’s new album, “Van Lear Rose.” The result: a blend of Lynn’s gritty, authentic vocals and lyrics and White’s raw, bluesy sound that garnered widespread critical acclaim and two Grammy wins (Best Country Album and Best Country Collaboration with Vocals), though praise among the country music press was much less muted.

Nelly had already been riding high for a couple of years based off some killer singles from his first two albums (2002’s “Hot In Herre” being foremost among them) but by 2004, he was looking for a hit. Enter Tim McGraw, whom Nelly handpicked for this crossover hit. McGraw’s vocals certainly add… something, but this falls more on the R&B/hip-hop spectrum than anything country. Still, audiences took it to the top of the charts that year.

Alison Krauss had been recording music for 20 years and had won numerous accolades by the time she collaborated with Robert Plant for this 2007 Grammy-winning album. The former Led Zeppelin frontman had been working with old bandmate Jimmy Page, as well as his own solo projects and other rock-oriented collaborations since Zeppelin’s 1980 dissolution, but veered into folk as he settled into his emeritus years. This made for a natural fit for Krauss’ bluegrass and country background, and their album “Raising Sand” garnered much critical praise and a slew of awards from the mainstream music press.

This honky-tonk/blues number had been around since the 1930s, so it was little surprise to see the classic dug up for Willie Nelson and jazz trumpeter Wynton Marsalis’ live 2008 album. Willie’s vocals, coupled with Marsalis’ horn and backed by his band, made for a lively rendition.

What could have been a cringey attempt at humor instead turned into a self-effacing (and yes, still cringey) moment at the CMT Awards in 2009, when Taylor Swift announced that she was now "T-Swizzle", and unveiled "Thug Story," a collaboration with T-Pain. 

Here's an unexpected musical teamup that worked quite well. Back in 2009, Sugarland and the B-52s took the stage together at the CMT Awards to play an incredibly high-energy countrified version of "Love Shack."

File this under “hip-hop and country legend collaborations that make perfect sense.” Snoop Dogg’s laid back, Long Beach stoner vibe was a perfect pairing with Willie Nelson’s, uh, laid back, Texas stoner vibe, and the two came together, predictably, over their shared love for marijuana. This 2011 collaboration wasn’t the first between the two — that would be Snoop’s 2008 “My Medicine” — but it’s arguably the most fun.

Country covers of R&B songs were nothing new by 2011 — indeed, Jennifer Nettles’ band Sugarland had recently done one with Beyonce, performing the superstar’s “Irreplaceable” at the 2007 AMAs — but this 2011 ACM performance with RiRi showed a new side for the Barbadian R&B queen. Unsurprisingly, Rihanna waltzed in like she owned the place, and her performance alongside Nettles showed as much.

Aerosmith’s most recent studio album got a big assist from Carrie Underwood, the most successful American Idol of all-time (according to Forbes). The hard rock outfit had always flirted with blues, glam, and metal throughout its storied career, but for this 2012 outing, they went countrified after meeting with Underwood in L.A. and laying down this power ballad. Despite some intitial skepticism from Joe Perry, the guitarist conceded that Steven Tyler and Underwood’s vocals were “just right.”

File this one under “well-intended hip-hop and country collaborations that didn’t work out as planned.” Brad Paisley’s attempt to start a dialogue on racism and Southern pride resulted in such cringeworthy lyrics and couplets like: “If you don’t judge my do-rag/I won’t judge your red flag” and “If you don’t judge my gold chains/I’ll forget the iron chains.” Seriously. Not surprisingly, the song was widely panned.

We would be remiss not mention Queen Bey here, who, as previously mentioned, performed her 2007 hit “Irreplaceable” with Sugarland at that year’s AMAs. “Daddy Lessons,” recorded for her 2016 seminal album “Lemonade,” blends country, blues, and zydeco to great effect. It also would help bring the Dixie Chicks back into the spotlight after a hiatus that saw them ostracized after their criticism of President George W. Bush and the Iraq War.