A great duet requires all the necessary elements— song selection, choice of musical partners, execution—to come together perfectly. Throughout the history of recorded music, there have countless examples of folks finding that perfect combination: “Ain’t No Mountain High Enough,” “What Have I Done To Deserve This?,” “Nothing Better.” But when it goes wrong or the pieces don’t quite fit together, it can elicit reactions ranging from amusement to pure revulsion. The history of alternative music, in all its shapes and guises, has yielded plenty of instances of duet greatness and folly. For this list, we are tipping our caps to those moments that produced complete train wrecks, noble failures, and glitches in the musical Matrix.
Luciano Pavarotti & Lou Reed – “Perfect Day”
Starting in 1992, Luciano Pavarotti held annual benefit concerts where he welcomed people from throughout the musical universe to raise funds for worthy causes, like the international aid agency War Child and the UN Refugee Agency. And naturally, that resulted in some truly surreal moments like Pavarotti sharing the stage with Spice Girls and British rockers Skunk Anansie. But by far the strangest pairing happened in 2002: Pavarotti with alt-rock deity Lou Reed. It wasn’t simply the sight of the wiry New Yorker next to the inflated Italian. No, it was listening to the two men try to find some common vocal ground on a version of Reed’s masterpiece “Perfect Day.” The shift from Reed’s sprechgesang patter and Pavarotti’s booming tones is dizzying and, frankly, hilarious.
Sinead O’Connor & Shane MacGowan – “Haunted”
If this pairing happened in, say, 1987 when Shane MacGowan’s former band The Pogues recorded their peerless holiday classic “Fairytale of New York,” it would have been a classic. Instead, it was eight years later when MacGowan had lost even more of his teeth and vocal abilities. So on this redux of a song The Pogues penned for the Sid & Nancy soundtrack, you are greeted with the angelic sound of Sinead O’Connor and a barely conscious MacGowan. The song kinda works because of that, as his tuneless croak befits the sound of a lovelorn soul tortured by memories of a past relationship. But in the spirit of the advice, MacGowan should have heeded with regards to booze and cigarettes, “Haunted” is best taken in moderation.
Nick Cave & Kylie Minogue – “Where the Wild Roses Grow”
A successful duet but an odd one nonetheless. And one that smacks of a pop star trying to scrape up some underground cred by slumming it with one of the cool kids. The truth is that Cave was a fan of Minogue and apparently wrote the tune with his fellow Australian in mind. Luckily she was game for it and handed over one of the earthiest and most impactful vocal turns of her ‘90s output. At the same time, the appearance of Cave and Minogue together feels unsettling, as if we’re just waiting for him to corrupt her into a haze of junk sickness or for her to inspire him to record his next album with Stock, Aitken and Waterman. Probably for the best that they only crossed paths for this brief, wonderful moment.
Jack White & Alicia Keys – “Another Way To Die”
On paper, not the worst idea in the world. In reality, a forgettable Bond theme and a case of one artist forcing another to play on their terms rather than finding some shared ground. Which meant Alicia Keys had to find her footing in the blues-rock world of Consolers of the Lonely-era White. To her credit, she doesn’t fall completely on her face here but stumbles through gamely while her duet partner spits out nonsense lyrics in his cod bluesman fashion. As much of a shambles as the Bond film (2008’s Quantum of Solace), it was ostensibly promoting.
Ice-T & Perry Farrell – “Don’t Call Me Nigger, Whitey”
One laudable aspect of Lollapalooza’s first incarnation in 1991 was to encourage these varied acts, touring North America together for weeks on end, to find ways to collaborate. That led to wonderful moments like Nick Cave joining L7 for “Andres” or Billy Corgan playing guitar for The Frogs. It also served up weirdness like Ice-T joining Jane’s Addiction for a rendition of Sly & the Family Stone’s minimalist Civil Rights tune. Bless these dudes for trying to hit the same challenging tone of SNL’s famous “Word Association” sketch, but at the time and today, it feels like the musical equivalent of Quentin Tarantino insisting it’s okay for him to use the n-word because he’s “not afraid of it.”