This week, 64-year-old reggae icon Jimmy Cliff releases Rebirth, an album produced by Rancid’s Tim Armstrong. It’s the latest in an ongoing trend that Flavorwire dubbed “inter-generational” musical collaborations: full-album pairings between an older legend and a younger industry stalwart. From Jack White and Loretta Lynn’s Van Lear Rose to Ben Folds and William Shatner’s Has Been, these pairings have always been around. But the last few years have seen a marked uptick. And so now, in our never-ending quest to make everything a competition, we evaluate some of the more prominent inter-generational collaborations, not based on the merit of their music, but on the inherent difficulty level they possessed. Using our foolproof “Revival of Beloved But Forgotten Artist” Difficulty-O-Meter, we figure out exactly which young, elder-respecting musician/producer overcame the biggest challenge.

Mavis Staples, You Are Not Alone (2010)

Producer: Jeff Tweedy
Age Difference: 29 years
Obscurity-to-Relevance Ratio: By 2010, Jeff Tweedy was as established a songwriter as they come, albeit one a few years removed from his peak. Meanwhile, Mavis, decades after her heyday with the Staples Singers, was on a latter-day upswing thanks both to her Ry Cooder–produced civil rights movement homage, We’ll Never Turn Back (2007), and the Obama campaign’s usage of the Staples Singers’ “I’ll Take You There.”
Obviousness of Pairing: Both Tweedy and Staples are from Chicago. Both are best known for their work in some strand of what can be generally grouped into the category of American roots music (gospel vs. country). And that’s about where the similarities end.
Result: Tweedy didn’t try to break Staples out of her game on You Are Not Alone, deciding to record with her touring band and to cover early gospel cuts. The result was rapturous reviews and Mavis’s first Grammy, for Best Americana Album. When she accepted the award, a clearly emotional Staples thanked Tweedy for bringing the “youngsters” to her and declared her victory “a long time coming.” Awww.
Analysis: Tweedy gets cred points for stepping out for his first non-Wilco production work in such unorthodox manner. But did he really do much heavy lifting? Bash out a couple of originals, dust off some classics, let Mavis do her damn thing, and boom, you got a Grammy.
“Revival of Beloved But Forgotten Artist” Difficulty Rating: 4.7 (out of 10)

Bobby Womack, The Bravest Man in the Universe (2012)

Producer: Damon Albarn
Age Difference: 24 years
Obscurity-to-Relevance Ratio: Even at 44, Albarn can’t stop being relevant. With Gorillaz all but officially behind him, Damon has ramped up his old crew Blur for an attention-grabbing London Olympics performance. (Why, just yesterday, a certain website gave him some shine.) Meanwhile, Womack hadn’t put out an album in 12 years, since 2000’s Christmas Album (no, like, that’s what it was called: Christmas Album) and was inducted into the Rock and Roll Hall of Fame, very much a shuffle-boarding-retiree kind of place, in 2009. Meaning: Good ol’ Bobby was a soul lion in winter.
Obviousness of Pairing: The two had already worked together, when Womack appeared, alongside Mos Def, on Gorillaz’s 2010 single “Stylo.” More importantly, Albarn’s ongoing quest to work with everyone ever in every single genre imaginable means no collaborator feels too farfetched.
Result: Albarn layered gloomy piano runs and stark drum machine beats under Womack; Lana Del Rey shows up on one track, a snatch of an old Gil Scott-Heron spoken-word vocal about God being broke on another. And, in at least some part because Bobby Womack’s voice would probably sound good on anything, the experimentation works. Says Womack now, “I’ve never gotten this kind of attention for any album I’ve ever recorded, and I’ve recorded 30 or 40 albums.”
Analysis: After Gorillaz, Albarn’s reputation as genius pastiche-genre curator is strong enough that anything he’d done with Womack would have gotten attention. Luckily, though, they made a dope album. Smart money’s on some Grammys down the line.
“Revival of Beloved But Forgotten Artist” Difficulty Rating: 6.9

Jimmy Cliff, Rebirth (2012)

Producer: Tim Armstrong
Artist: Jimmy Cliff
Age Difference: 18 years
Obscurity-to-Relevance Ratio: This might be as even a ratio as this list sees. While reggae legend Cliff’s peak (general consensus: His double-dip on the soundtrack and onscreen for 1972’s The Harder They Come) came way before Armstrong and Rancid’s (general consensus: 1995’s … And Out Come the Wolves), both men are, to some doe-eyed youngsters, legacy acts.
Obviousness of Pairing: The line is clear: Rancid worships at the altar of The Clash, The Clash worshiped at the altar of Jimmy Cliff. Bassist Paul Simonon, in particular, was obsessed with The Harder They Come. On “The Guns of Brixton,” Simonon references Cliff’s character in the movie: “You see, he feels like Ivan / Born under the Brixton sun.” On Rebirth, Cliff covers “The Guns of Brixton.”
Result: Rebirth, released last week, brings Cliff back to his beginnings. Explains NPR’s critic Will Hermes, “Frankly, he’s made a lot of lukewarm crossover LPs over the years, but he finally decided to rewind his sound with … Armstrong, [who] helps nail that old-school sound throughout this record … If anyone should be able to reanimate the vintage Jamaican music I hear bumping out of every other hipster coffee shop in town, Jimmy Cliff is the man.” Also worth nothing: Cliff’s voice is as clean and crisp as ever.
Analysis: Jimmy Cliff does Jimmy Cliff, after Tim Armstrong prods and pokes and cajoles him into it. An appreciated, if not necessarily backbreaking, bit of labor.
“Revival of Beloved But Forgotten Artist” Difficulty Rating: 3.4

Jamie xx and Gil Scott-Heron, We’re New Here (2011)

Producer: Jamie xx
Age Difference: 40 years
Obscurity-to-Relevance Ratio: Scott-Heron, who passed away last year, has always loomed large over hip-hop, thanks both to his credit as an early innovator of the form and the continued sampling of his work. But before his 2010 album I’m New Here, Scott-Heron hadn’t released an album in 16 years. As The New Yorker‘s harrowing profile from the time explains, he’d been struggling with a crack addiction for years. The trajectories couldn’t be more dissimilar: Young buck Jamie xx, a member of newfound indie darlings The xx and an in-demand DJ in his own right, was (and is) on the up-and-up.
Obviousness of Pairing: Unexpected, but not completely so, as GSH’s influence ranges wide and far. But the path to fruition was pretty damn circuitous. I’m New Here came about because Richard Russell, head of XL Recordings and the producer of the album, talked Scott-Heron into it. As The New Yorker explained, “Scott-Heron recorded the songs and his poems, and Russell added the hip-hop tracks that accompany them. ‘This is Richard’s CD,’ Scott-Heron says. ‘My only knowledge when I got to the studio was how he seemed to have wanted this for a long time.'” Russell then talked Jamie, whose band is signed to XL, into reworking the whole thing again. Jamie met with Gil a couple of times during the process, but mostly corresponded via the mail (like, the regular mail), and at one point before the album’s release explained that Scott-Heron’s “kind of a bit off the map again. Which happens. He still needs to approve some of my music videos, and I can’t get ahold of him.”
Result: Simply: We’re New Here — a refined melding of Scott-Heron’s detached heartache vocals and Jamie xx’s steely beats — is gorgeous. And it’d go on to have a second life when its last track, “I’ll Take Care of U,” got reappropriated by Drake as “Take Care.” Explains “Take Care’s” producer, Noah “40” Shebib: “That song we just loved … [We] felt that song never got its shine. What a great record! How come this song never was as big as it should have been?”
Analysis: A mighty task, conquered. Staring in the face of the challenge of old-timey letter-writing, Jamie xx crafted something wholly new and original.
“Revival of Beloved But Forgotten Artist” Difficulty Rating: 8.7