The Oscars' Best Original Song category is responsible for Juicy J having as many Academy Awards as Christopher Plummer, and yet I still hate it. That's how bad it is. We could have built an entire Oscar-travesties ballot consisting of nothing but egregious Best Song snubs and inexplicable Best Song winners. No Oscar category is more broken, or operates from a more antiquated methodology; Best Original Song is a travesty-generating machine. Given the choice in the first round, Grantland's readers voted pretty overwhelmingly that Samuel L. Jackson losing to Martin Landau constituted a bigger blot on the Oscars' legacy than the entire ignominious history of the Best Song category as a whole, which means we didn't get to fully explore said ignominy. So let's do that now.

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.