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

52) “Kid vs. Play (The Battle),” from House Party (1990)

If there’s a rap battle in an earlier American narrative feature, I don’t know of it, and if there’s a more fun charismatic rap battle in a movie I don’t know of it either. The disses in “Kid vs. Play” are not set to kill—probably the most personally disparaging comment either makes is when Play calls Kid “Eraserhead”—but it’s a lot of fun precisely because of how mild the attacks are. It wouldn’t be believable to watch the two of them do much than rag on each other in that way that friends typically do, for one thing. For another, this is the best way to sense the creativity that the two of them are able to channel at a moment’s notice. The dance off earlier in the film is great, but Kid ‘n Play aren’t dancers by trade. Getting a chance to hear them play catch with one another here is a joy because it’s so cinematic; you can imagine people battle rapping at a party like this, but it’s just a smidge beyond real life to visualize people doing it this agreeably and this smoothly.

53) “Salve Regina,” from Sister Act (1992)

Let’s say you were thirty years old in 1992 when Sister Act opened. First of all, you are unironically my target audience. More relevantly, a thirty-year-old in 1992 brought up Catholic would have no real memory of a pre-Vatican II world. It might only be a slight exaggeration to say that the implementation of the ideals of Vatican II was the most important thing to happen to Christianity since Martin Luther decided to do a home edit for Roman Catholicism. There had always been at least a little humor in filmic nuns, a problem as insoluble as Maria, but Sister Act fairly blew the roof off with Whoopi Goldberg’s lounge singer Deloris masquerading as “Sister Mary Clarence.” It’s not merely that Whoopi Goldberg is bopping around the stage with Wendy Makkena and Kathy Najima, but that this is Catholicism according to the hopes of Pope John XXIII and Larry Norman alike. Sister Act is funny because of Goldberg, but there’s nothing kooky about this performance of “Salve Regina” with handclaps and vocal runs. This is contemporaneous with Amy Grant, Jars of Clay, Steven Curtis Chapman, Michael W. Smith. (Those of you thinking about the earlier crossover success of gospel performers like Mahalia Jackson and the Edwin Hawkins Singers as precursors are being really nice to contemporary Christian.) The rise of a type of Christian music that could sound like pop if you didn’t listen to the lyrics is essential to so much of the marketing of today’s Christianity. Deloris needs a project and the people at Hillsong are (presumably) true believers. But they’re both aiming their performance at the kids who look into the church with quizzical looks on their faces.

54) “Hakuna Matata,” from The Lion King (1994)

Several years ago, before Sub Titles, my cohost Matt and I made a list of the 100 most ’90s songs. At number 27, lodged between “I Want It That Way” and “Black Hole Sun,” rests “Hakuna Matata.” (I sort of can’t believe it was that low, but I used way more capital getting “Flagpole Sitta” into the top ten, so you can blame Harvey Danger.) Simba’s pre-wildebeest childhood, living on Africa’s answer to the Aggro Crag, lit in salmon and teal, and absolutely certain nothing bad could ever happen to him, is the bourgeois vision of the 1990s in two dimensions. “Hakuna Matata” is no longer the phenomenonal song from this movie that it used to be, given that the “Circle of Life” sequence is far more impressive and that everyone seems to have their own favorite based how frequently played this was. That scene at the end of Toy Story where they’re listening to “Hakuna Matata” in the car doesn’t include that song for some kind of ironic comment about what’s happening to Woody and Buzz. It’s got “Hakuna Matata” in it because it’s exactly what Andy’s mom would be playing to appease her kids on a car trip. It was ubiquitous, and it was a mission statement too. Simba sings about how you don’t have to worry about anything after his dad was killed rescuing him, and this forcible blindness is his guiding light for the next several years.

Three days before this movie got its L.A. release, Nicole Brown Simpson and Ronald Goldman were stabbed to death. It is entirely conceivable that the same people taking their kids to The Lion King when it opened wide on June 24th were glued to their TV sets one week before, when a white Ford Bronco led a low-speed chase. If the country’s reaction at large to the Rodney King verdict was that it was an isolated incident (like the Watts riots had been “isolated”), then you could practically hear white America intoning “It’s our problem-freeee philosophyyyyyy” over the sounds of the sirens.

55) “That Thing You Do!” from That Thing You Do! (1996)

Even if you put aside the abiding love that Tom Hanks has for typewriters, he would still be one of our nation’s chief nostalgic figures. He’s become a figure of the 1990s for people who wish they were still kids, but something like Forrest Gump means that he appeals to be people his own age wishing they were still kids. It’s a sickness, and the only prescription is Adam Schlesinger. That Thing You Do! is a perfectly fine movie, a film where you hear the title song more often in under two hours than you’ll hear your own name called in a week. Hanks, the old-fashioned auteur of this movie, lines up the nostalgia. Adam Schlesinger lines up the music, fabricating an honest-to-goodness ’60s pop-rock hit out of the 1990s. It’s a fabulously catchy song (though not even my favorite song from the film, weirdly), and it’s the reason this movie sings. “That Thing You Do!” is like that Italian song in fake English, a perfect anthem to wishing it were still 1964/you were still eighteen, but without any of the baggage that “Doo Wah Diddy Diddy” or “Don’t Let the Sun Catch You Crying” would have come with.

56) “I Say a Little Prayer,” from My Best Friend’s Wedding (1997)

I don’t really know what to make of this sequence. I’ve never really known what to make of this sequence. Is this scene as brilliantly infectious as its partisans would have you believe, not merely because Rupert Everett manages to chew scenery within a scenery-chewing performance, but because there are people waving their lobster-clawed hands in the air? Or is this scene really as bizarre as the first few moments of it the first time around, just an absolutely nutty thing to happen even by the standards of the ’90s romantic comedy? On a probability spectrum, I feel like this is even less likely than the Kid ‘n Play rap battle to happen in a real setting. This is what you come to My Best Friend’s Wedding for, because Julia Roberts feels horrifying things in this movie and Dermot Mulroney is playing someone with a moderate concussion (I think, right?). It’s not a romantic movie in any sense of the word, and as many hijinks are there are in this thing, it’s a little too devious for me to feel like I’m supposed to bellylaugh. No, this is lunacy we come for in the ’90s romcom, a lunatic moment amplified by big hats and big men singing big notes and, yes, the waitstaff at this restaurant not even being slightly annoyed by this ersatz recital.

57) “Wise Up,” from Magnolia (1999)

We’re all connected in some mystical circle of life, Magnolia finds, not that I’ve ever thought that film was all that great at bringing that forward. (The most powerful musical performance in a PTA movie, as far as I’m concerned, is Philip Seymour Hoffman singing about getting Joaquin Phoenix on a slow boat to China.) Not everything works in this bloated movie, not by a long shot, but I’ve come around on the power of “Wise Up” as a song where most of the key characters get a line or two. Maybe they’re all singing this song at once, maybe none of them have a clue who Aimee Mann is, and whatever the answer it doesn’t really matter. What’s great about this scene is the deep, inconsolable honesty that these people are feeling, people who overwhelmingly have been lying to themselves or making a show for the sake of expectations. Many directors have, and will, put a song over a montage of multiple characters; this is the way television programs can’t help but end episodes. Paul Thomas Anderson’s commitment to the idea, to put the words in his characters’ mouths rather than surrounding them with the musical equivalent of a luminiferous ether, is unique.

58) “Blame Canada,” from South Park: Bigger Longer & Uncut (1999)

It’s not often that you get to one-up a joke from The Simpsons, but brevity is the soul of wit. “Itchy & Scratchy & Marge” is a little too gassy and self-righteous to actually be funny. “Blame Canada,” on the other hand, limited to like eighty seconds of music, is hilarious. Our kids suck, the parents find, desiring only to “fart and curse.” Why do the kids suck? The government? society? television? The turnaround from the dads singing that last line out to the absolute sharpness of Sheila replying, “No! Blame Canada!” is so wonderful, and the fury of the lyrics only make this totally dumb joke even funnier. Like The Simpsons, South Park has only gotten worse (so much worse) as it’s become the establishment. It’s almost shocking to return to a song like this and remember just how good it was at putting skewers through sacred cows. The kids suck, of course, but with every crappy kid, surely there’s an excrementitious parent hanging around somewhere.

59) “You’ve Got a Friend in Me,” from Toy Story 2 (1999)

Hey, look, Tom Hanks and nostalgia again. “You’ve Got a Friend in Me” hadn’t actually appeared with a character from the films singing it until Toy Story 2, and when that happened, it happened to bring Woody back to being the kind of person who could embrace death. “You’ve Got a Friend in Me” was probably the second-favorite song from an animated movie of 1995—”Colors of the Wind” almost got on this list—and everyone seeing Toy Story 2 must have known the song already, as well as being vulnerable to its signification within the world of the Toy Story characters. Woody and Buzz both react to it when they hear it, and Woody wants to return to Andy when he hears it…just as we, in the audience, would also return to the original joy of seeing Toy Story when we heard it. In retrospect, this doesn’t seem nearly as fiendish a tug on our heartstrings as some of the more histrionic stuff that happened in the inferior sequels following this one. That’s why this is a smart nostalgic pull rather than a manipulative one. Toy Story 2 is using its predecessor to make its characters feel something for the past which will then relate back to us, rather than reaching through the screen, grabbing us by the collar, and yelling “REMEMBER HOW YOU WERE YOUNGER WHEN YOU INITIALLY DEVELOPED FEELINGS ABOUT THIS FRANCHISE.” In other words, this is a brilliant usage of the song, a missive from former Woody to present Woody which will allow future Woody to thrive.