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The 10 Best (and Worst) Best Song Oscar-Winners of All Time

From ‘Over the Rainbow’ to ‘It’s Hard Out There for a Pimp,’ the Best Song category’s cream of the crop – and bottom of the barrel

The magic of the movies depends on sound as much as sight, and ever since the Academy of Motion Pictures and Sciences established the Best Song category for the seventh annual Academy Awards in 1933, the Oscars have honored the finest show tunes, pop tunes and rock-to-rap bangers ever to grace the screen. Or at least, they’ve tried to. As with any other category, the gold has gone to stone classics and stinkers alike; more often than not, the winners tell us as much (or more) about the values of the era as the value of the songs themselves. 

We’ve already delved into the 20 greatest Best Song performances at the Oscars, paying lip service to nominees ranging from “Endless Love” to “Everything Is Awesome!” But what about the songs themselves? Which of the winners rank head and shoulders above the rest? And which ones feel like a painful punch in the gut every time you hear them? For your listening pleasure (half the time, anyway), we’ve cued up the 10 best and the 10 worst Best Song winners of all time. Are they all worth listening to if you want to understand the Oscars? As one winner put it, you’re daaaaaaamn right.

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Best: “Into the West” (‘The Lord of the Rings: The Return of the King,’ 2003)

Think of this as the Sméagol to the Gollum of “My Heart Will Go On.” Like that titanic track, “Into the West” is the climactic power ballad of a three-hour-plus, billion-dollar-grossing epic, created as a collaboration by a respected film composer and an established pop star with serious vocal chops. But where “Heart” steamrolls, “West” soars and soothes. Co-written Fran Walsh (co-screenwriter of the Rings films), composer Howard Shore and Eurythmics alumna Annie Lennox, it builds to its bittersweet high notes with true Tolkien-ian splendor. 

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Worst: “We May Never Love Like This Again” (‘The Towering Inferno,’ 1974)

Today, we think of Seventies Hollywood as the stomping ground of maverick masters like Scorsese and Coppola, and the birth of the blockbuster era midwifed by their pals Spielberg and Lucas. Yet the decade was dominated by big-budget, star-studded disaster movies that were every bit as popular and ubiquitous as superhero movies are today. And two of the genre’s biggest box-office successes took home Best Song Oscars: “The Morning After” from The Poseidon Adventure, in 1972 – and this virtually identical track from The Towering Inferno two years later. Both are collaborations between singer Maureen McGovern and songwriters Al Kasha and Joel Hirschhorn. And while it was tough to pick which one was more offensive to human ears, let’s just say “We May Never Love Like This Again” won for a reason. We may never hear anything the same ever again.

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