To see the intro to this project, as well as links to other decades, click here.

60) “Man of Constant Sorrow,” from O Brother, Where Art Thou? (2000)

I don’t think any movie has ever used the word “damn” to humorous effect quite like O Brother. “Damn we’re in a tight spot!” is one of the great refrains of any movie from this century, and thinking about “Hot damn! It’s the Soggy Bottom Boys!” could get me to giggle at a funeral. It’s what everyone in this scene is thinking as the mystery group busts out their one and only tune, “Man of Constant Sorrow,” at a particularly ticklish moment in local political life. On an absolutely loaded soundtrack, this song is probably the headliner, and the soundtrack had genuine crossover appeal. It was the second (and as of now, the last) film soundtrack to win the Grammy for Album of the Year, and the company that this soundtrack keeps is telling. Like the Saturday Night Fever soundtrack, which gave disco the CPR that real ones know it deserved, O Brother, Where Art Thou? reintroduced so many people to old-fashioned country and bluegrass music. “Man of Constant Sorrow” is, as the film clip shows, a tremendous crowdpleaser, a good song for a guitarist with a little flair and an opening for a lead singer to lead tight harmonies. In true Coen Brothers fashion, it’s also a song that feels completely ill-suited to make a room of people go nuts and shout “HOT DAMN” at the top of their lungs, eyes bugging out of their heads. The title of the song does the work for us, but the lyrics themselves are absolutely a bummer too. Yet the Depression-era crowd goes mad for it, and so does too the theater audience.

61) “Tiny Dancer,” from Almost Famous (2000)

The older I get, the more I really don’t like this movie at all. But Cameron Crowe, before he became an absolute parody of himself—writer-directors who only have one or two ideas tend to get there pretty quick!—had a way of making songs do the work that his actual writing couldn’t do. In Say Anything, the most eloquent part of the film is John Cusack’s lanky frame propping up Peter Gabriel. And in Almost Famous, he takes another song that everyone loves and tosses it into our midst and lets us hungry hungry hippo it up. This is still a genuinely effective scene, even if I think it’s a little cycnical. The band reconnects because of a great song, reveling in its own communal feeling, and being where the audience cannot, we feel like we’re part of some secret society within the secret society of ’70s rock. There’s an ungenerous part of me that wants to blame Almost Famous for one of my least favorite trends in movie music, which is to use our previous devotion to a song as an unearned way to emotional resonance. (We’ll get there next decade.) On the other hand, it may also be that a mix of needledrop and performance this right is simply alchemical, and you can’t blame a movie for stirring up a little magic.

62) “Seasons of Love,” from Rent (2004)

My dad says that when he was a kid going to Mass, they broke out “Let It Be,” because…”Mother Mary comes to me,” y’know. Maybe he was pulling my leg, but I can report firsthand that the church youth choir I was in did “Seasons of Love” in church in the mid-2000s, and it was not the idea of any of the kids in said choir to do so. (I want to shout out the Catholics for having superior musical taste to the Methodists, great job y’all.) “Season of Love” would be the worst song in most musicals, though I guess luckily for “Seasons of Love” it shares a playbill with “La Vie Boheme,” which is one of the songs they play in the malls in Hell. “Seasons of Love” has the pretentious shallow depth of a Mumford and Sons song, and in 2004 I think Americans were aching for music that felt like chugging a Diet Coke. “Seasons of Love” borrows from Eliot (“I have measured out my life with coffee spoons”/”in cups of coffee”), and then comes to a conclusion about the human condition which no self-respecting poet would come to: measure in love. It was a vulnerable time, a frightening time, an unmoored time. “Seasons of Love” is the kind of thoughtless balm that pulverizes the mind and relaxes the nerves, and it only adds insult to injury that Traci Thoms and Jesse L. Martin are such talented singers.

63) “A Waltz for a Night,” from Before Sunset (2004)

Every time, Julie Delpy has a better voice than I remember. I always remember this song as being a little pitchy or out of tune, maybe because the guitar is a little clumsy. Delpy’s voice here is not merely adequate, but perfect for the moment. Quiet, breathy, frank but still modulated, “A Waltz for a Night” is not really about the words or the chords but about the romance. This is one of the most romantic moments in any movie I’ve ever seen, and Jesse doesn’t quite know what to do about the beauty of Celine’s vulnerability. This is a secret song, one that I cannot imagine she ever thought she’d play in front of its target audience, and it reveals a depth of feeling that Celine, so straightforward and logical and efficient, has unfolded only the barest handful of times across two films. Part of the pleasure in the Before movies is in how far away they are from one another, about how distant they are from each of the other installments. We don’t hear Celine sing again, but we know that Jesse must. Surely this is the voice that sings while washing dishes or tucking twins into bed or walking around the neighborhood. It’s the voice of a Celine he’s never met before, and one he will come to know, and perhaps lose, in the ensuing decade.

64) “Jingle Bell Rock,” from Mean Girls (2004)

Gretchen Wieners, struggling with her new role in the choreography (” murders Jason with a boombox or something. Disaster has struck, the high school talent show of cataracts and hurricanes. The Plastics are invincible because they’ve never been defeated, not because they can’t be defeated, and this moment where the music for this ninety second dance routine they’ve got has disappeared and cannot be pulled back is Waterloo in the making. And then, the ringer in the group pipes up. “What a bright time, it’s the right time…” and away we go with audience participation and a teacher coming up to play the piano part and the day is saved. Mean Girls, by now about as useful for understanding the youth as The Blackboard Jungle or Boys Town, does at least make one point in this scene that I think is still meaningful. The food chain where the Plastics are the apex predators is held up by prey that is more than happy to prop them up. Now would be the moment to let them fall flat on their faces, and while Cady probably could have let this end awkwardly to accomplish Janis’s eighth-grade revenge, and while the auditorium probably could have stayed silent rather than building up the group sing, they rise triumphantly. Americans are not particularly good at kicking their bullies while they’re down.

65) “And I Am Telling You I’m Not Going,” from Dreamgirls (2006)

Who knows that Jennifer Hudson wouldn’t have hit it big if she hadn’t gone on American Idol, but I think it’s fairly safe to say that she wouldn’t have won an Oscar before she turned twenty-seven without it. In a time when it seems like everyone in movies has a dad who’s a vice-president at Goldman Sachs and a mother who can claim an ancestor in the Four Hundred, it’s almost refreshing to think that a reality TV competition could procure the talent put in direct contrast to literally Beyonce. Dreamgirls is not much of a movie, even if the soundtrack is better than you remember, but the movie is two-plus hours which exists to serve this singular performance. “And I Am Telling You I’m Not Going” fits into a lineage with “Over the Rainbow,” “My Man,” and “Mein Herr,” although you can see the diminishing returns from that list already. It is the announcement of a supreme vocal talent, and in the 21st Century, where being famous for fifteen minutes means you tweeted something you shouldn’t have, you don’t have to be a Broadway wunderkind or the daughter of Judy Garland to get five minutes of earthshaking solo. You just need to get Simon Cowell to like you.

66) “Anyone Else but You,” from Juno (2007)

I promise I like movies from the 2000s (two of my absolute favorites are in this post!), but here’s another installment where I’m pretty far away from calling this a good movie. This came out at just the right time, and I had just the right friends, and so even now I know this soundtrack like the back of my hand. “He is the cheese to my macaroni” is…rough. And the song playing behind Elliot Page riding to see Michael Cera is “Tire Swing,” a Kimya Dawson number that is probably playing on the same perfidious Spotify playlist that “La Vie Boheme” is on. But this rendition of “Anyone Else but You,” a Moldy Peaches cover, gets at what was most prized in this moment in American indie movies. After a bunch of snark and stomach-turning cleverness, the goal is bilious good cheer, preferably seen from enough of a distance that you don’t have to admit that you like Weimaraner puppies or Michael Cera that much, dweeb. Thanks to Page and Cera’s mousy little voices, all you can smell is cheese.

67) “That’s How You Know,” from Enchanted (2007)

That same defensiveness about sweetness even infected Disney movies at this time. Enchanted got raves because Amy Adams was terrific and because the movie was pretty in pastels, but mostly because it was evidence (“evidence”) that Disney had developed a sense of humor about itself. That’s impossible, because corporations aren’t people or even animals and thus are fresh out of the capacity for humor, but Enchanted is based on the premise that if you put a Disney princess in New York City, it’d be pretty weird for her. Thus the sight gags of rats with and without wings scrubbing toilets, or James Marsden getting reamed out for stabbing a bus. I’m not immune to this. Patrick Dempsey’s reading of “He knows this song too?…I’ve never heard this song” continues to hit the spot for me. Yet here, more than any other part of the movie, you can sense the movie’s discomfort with Vermont-tier sappiness. Of course, like Juno or the Steak-umm Twitter account, the point is to play both sides, to continue to hit us with the brand values while looking like they’re still the cool mom. In this number, probably the most contagious song from Enchanted, we get an object lesson in this humorless, nominally self-effacing corporate planning.