Ranking Intergenerational Musical Collaborations from Best to Worst


This week sees the release of The Bravest Man in the Universe, the intriguing new record that teams iconic soul vocalist Bobby Womack with Damon Albarn and XL Records founder Richard Russell, both of whom handle production duties. It’s an intriguing proposition on paper, and on record, the results are thoroughly excellent listening. The intergenerational nature of the collaboration, which also features an unlikely duet with Lana Del Rey — and the news this week that John Cale is working with Danger Mouse — has got us thinking about other occasions when artists from different musical eras have gotten together and produced music to bridge the generation gap. Sometimes it works, and sometimes, well, it doesn’t. We’ve ranked a few of the most notable such collaborations from best to worst. Let us know what you think.

The KLF and Tammy Wynette

This was all kinds of genius, and looking at it 20 years later, we still can’t quite believe it actually happened. Why aren’t there any bands like the KLF any more?

Gil Scott-Heron and Richard Russell

Bobby Womack, of course, isn’t the first artist whose career Richard Russell has attempted to resuscitate. He tracked down Gil Scott-Heron and basically strong-armed him into making I’m New Here, which was a thoroughly fine album in its own right and which now has the added (and sad) historical significance of being Scott-Heron’s last recording.

Johnny Cash and Rick Rubin

Rick Rubin’s albums with the mighty Johnny Cash are the gold standard for the whole terminally-underrated-old-dude-gets-unlikely-career-resurrection idea. These days, it’s Cash’s valedictory cover of Nine Inch Nails’ “Hurt” that seems to get all the attention, but there’s plenty more goodness to be found on the six records Rubin and Cash made together, which include similarly unexpected covers, reworkings of old standards, and a healthy number of originals. We’re particularly partial to Cash’s version of Nick Cave’s “The Mercy Seat,” a song that he was surely born to sing.

Jack White and Loretta Lynn

And while we’re on unlikely crossover collaborations, what about Van Lear Rose, country doyenne Loretta Lynn’s 2004 comeback album that featured production and the occasional co-writing credit from musical man-for-all-seasons Jack White? It wasn’t quite as bizarrely amazing as Tammy Wynette singing with The KLF, but it was pretty great nonetheless.

Iggy Pop and Peaches

You can imagine that Iggy and Peaches would get along like a house on fire, and there certainly seems to be genuine chemistry on this track, despite the generation gap and the markedly different genres in which the two work. Perhaps the best part of the whole thing is the gentle fun they poke at each other (“I wanna be your cat!” “Screw that…”).

The Ramones and Phil Spector

No one’s arguing for a minute that this was a particularly pleasant experience for anyone involved — especially poor Dee Dee Ramone, who had Spector pull a gun on him, which is even more terrifying given what the world knows about the lunatic producer now — but the results were thoroughly excellent. It’s not as unlikely a collaboration as it sounds, either, given the debt that the Ramones owed to ’50s bubblegum pop.

David Bowie and Bing Crosby

A staple on “most unlikely collaborations of all time” lists, and for good reason — even Bowie seems to wonder what on Earth he’s doing there. We rather like the result (which is why we also included this on our list of great pop/rock collaborations a couple of weeks back), but we appreciate that it might not be to everyone’s taste.

Bob Dylan and Kurtis Blow

Behold: Bob Dylan rapping. Seriously. (Skip ahead to about 6:20 to hear him and Kurtis trading lines like combatants in the world’s most unlikely rap battle.) Quite how this came about is unclear, and we’re not quite sure what we feel about it — the whole idea sounds too absurd to be true (and yes, Dylan fans, we are aware of the idea of that “Subterranean Homesick Blues” was an influence on the evolution of hip hop), but the result has a certain charm. And whatever you think of Dylan’s contribution, Kurtis is in fine form throughout.

Paul McCartney and Michael Jackson

This pretty much defines the phrase “less than the sum of its parts.” We’re not diehard Beatles fans here at Flavorpill, but still, there’s no doubt that McCartney is a songwriting genius, and at the time they worked together, Michael Jackson was at the peak of his powers. The result of their collaboration, then, should in theory have been something special. Instead, it was a thoroughly forgettable and rather insipid pop tune. Music — it’s difficult, isn’t it?

Metallica and Lou Reed

The less said about this, the better.

Natalie Cole and Nat King Cole

Drenched in saccharine, and kinda creepy to boot, considering that Nat King Cole had been dead for a quarter-century when his daughter recorded her half of the duet. Unforgettable, alright — but not for the right reasons, sadly.