Given the heights the 90s took Best Original Songs to at the Oscars, it’s surprising how quickly the category lost momentum. There’s still some great work to be found, but the highs definitely aren’t as soaring–indicating the direction the category would continue to go in the 2010s.
10. “It’s Hard out Here for a Pimp,” Hustle and Flow (2005)
Yes, this really won an Oscar. No, it did not deserve it. Dolly Parton was the frontrunner but my guess is people threw their votes this way because they thought it would be funny. It wasn’t, and it still isn’t (hey Academy, Dolly Parton is still waiting on that Oscar).
9. “Into the West,” The Lord of the Rings: Return of the King (2003)
I love Annie Lennox, but there’s no denying that this song is terminally boring. It’s saved from last place because Lennox does execute some flawless vocals (of course) and the music is pretty, if not memorable in the slightest.
8. “I Need to Wake Up,” An Inconvenient Truth (2006)
There’s nothing subtle about “I Need to Wake Up,” a call to arms about how everyone needs to do their part to make the world a better place. That isn’t necessarily a bad thing–if it was easy, we wouldn’t need to hear it in the first place, after all. For what it’s worth, Melissa Etheridge sells the hell out of it. But it’s such an obvious “message” song that its overall impact gets dulled by its own ambition.
7. “Al Otro Lado del Río,” The Motorcycle Diaries (2004)
“Al Otro Lado del Río” doesn’t sound like any other Best Original Song winner, and not just because it’s lyrics are in Spanish. It’s a subtle, sumptuous song that captivates with its simplicity. But that same simplicity ultimately leaves it crowded out of the front of the pack.
6. “If I Didn’t Have You,” Monsters, Inc. (2001)
I called Randy Newman’s other Oscar-winner (“We Belong Together”) passed its expiration date, but this win came during fresher days. Especially when performed by stars Billy Crystal and John Goodman, it’s a very charming song about a bromance for the ages. It sells itself so well that you don’t really notice the substance is relatively slight.
5. “Things Have Changed,” Wonder Boys (2000)
I give a lot of extra credit to songs that either tie back to the theme of the movie they come from or give the movie a lift. “Things Have Changed” only tenuously does either for Wonder Boys, but it is a great song in classic Bob Dylan style. Of all the songs on this list, it’s the only one I’ve owned (for whatever that’s worth). It’s also the only song on this list capable of existing separately from its movie–which is both a mark for and against it for our purposes.
4. “The Weary Kind,” Crazy Heart (2009)
A movie about a down-on-his-luck country singer should have a hell of an original song to help sell it, and Crazy Heart didn’t skimp in that department. “The Weary Kind” is perfectly in step with the tone and theme of the movie, and it’s a good song, too. I had forgotten the song completely until I looked it up for this, which is a mark against it, but when I hit play I was surprised to find a hidden gem among the winners of this decade. It’s appropriately weary and wistful, but it has hope to it, too.
3. “Jai Ho,” Slumdog Millionaire (2008)
Slumdog Millionaire was a runaway favorite at the Oscars in 2008 in part because of its infectious charm and the way it made audiences leave the theater feeling good. It’s no surprise, then, that “Jai Ho” plays conspicuously over the end credits with a massive Bollyw00d-style music video featuring all the cast members dancing in a train station set. Would audiences have felt so good walking out of the movie without that last impression? Maybe, but I don’t think so. It’s not my favorite song on this list by a longshot, but you can’t deny the role it played in Slumdog‘s success.
2. “Lose Yourself,” 8 Mile (2002)
Remember how “Al Otro Lado del Río” doesn’t sound like any other Best Original Song winner? That’s actually a common theme in this decade, because neither did “It’s Hard out Here for a Pimp,” “Jai Ho,” or this one. Ostensibly, “Lose Yourself” has the most in common with “It’s Hard out Here for a Pimp,” but they actually couldn’t have less in common. “Lose Yourself” has the tropes of a Best Original Song winner dressed up in stylish new clothes. I’m not a fan of Eminem, the movie, or the song, but you can’t deny this has all the hallmarks of the genre–and it makes for a fist-pumper of an anthem.
1. “Falling Slowly,” Once (2007)
I wasn’t a fan of the movie, where I thought the male character in the romance was too much of an asshole to be a proper romantic lead. But this song, a bittersweet and melancholy love story, gives all the feels. It feels urgent and poetic in its devastating simplicity. It’s not surprising at all that this song helped Once transition to Broadway, where it won another round of critical acclaim and the Tony Award for Best Musical. That’s how poignant this song is.
Next, we’ll go back to the Best Original Song winners of the 1990s, but you can also look at my Academy Awards page for much more content.