1. Simon & Garfunkel, The Graduate (1967)

Mike Nichols didn't invent the idea of using pop songs in movies, but by scoring much of The Graduate to the songs of Simon & Garfunkel, he redefined how pop music would be used from then on. Taking cues from the yearning melancholy of "Sounds Of Silence," "Scarborough Fair," and "Mrs. Robinson," the latter of which was penned especially for the film, Nichols let the music do the talking during long, otherwise wordless sequences, reflecting the inner monologues of characters who didn't always know what they wanted, only that they wanted more than they had.

2. Cat Stevens, Harold And Maude (1971)

At the beginning of Hal Ashby's cult classic, Bud Cort (Harold) descends the creaky steps of an old manse with his brown boots clicking morosely on the wood floor until he reaches an old Victrola and drops the needle on Cat Stevens' "Don't Be Shy." Given that he closely follows that action with one of his numerous staged "suicides," Stevens' hopeful folk initially seems like an odd choice. Then Harold meets the 79-year-old Maude. As the film transitions from sparse dialogue and the bleakness of Harold's house out into the world and Maude's carpe diem tossed-off wisdom, the music begins to weave into the story—Maude actually performs one of the tunes herself at a player piano—and carries it along to its infamous finale. Only two of the tracks were recorded specifically for the film, with "If You Want To Sing Out, Sing Out" putting Maude's rosy worldview to music. Yet the previously released "Trouble" also works perfectly, as Harold comes to terms with the impossibility of their romance. Harold And Maude is a small story with only a few characters, and Ashby's choice of a single songwriter to accompany their tale has appropriately been deemed one of the hallmark marriages of music to movie.

3. Aimee Mann, Magnolia (1999)

Three hours of raw nerves and frantic epiphanies, P.T. Anderson's third feature could fairly be described as operatic emo, transforming the nakedly personal into a resounding chorus of human misery. But about two-thirds of the way through, Anderson suddenly slams on the brakes: Relieved from their grief and heartache, his dozen or so major characters quietly sing along, one at a time, to Aimee Mann's "Wise Up," one of a few gorgeous songs that serve as the film's lifeblood. The chief lyric ("It's not going to stop until you wise up") speaks kindly but firmly to people suspended in an endless cycle of guilt and dysfunction, with the younger generation indelibly imprinted by their elders' misdeeds. It's the first break in clouds that will open up later—first in a Biblical "rain of frogs," and then finally in a generous coda, set to Mann's "Save Me," that lets a little sun shine through.

4. Leonard Cohen, McCabe & Mrs. Miller (1971)

Robert Altman selected three tracks from Songs Of Leonard Cohen—"Stranger Song," "Sisters Of Mercy," and "Winter Lady"—to serve as pretty much the entire score for his hazy revisionist Western, and over the years, even some Altman fans have complained that the Cohen songs are too samey and mopey, and that they date the film. Those nay-sayers are wrong, wrong, wrong. The way Cohen's lyrics echo the plot are often too uncanny, from the prophetic introduction of the gunslinger McCabe via the line "He was just some Joseph looking for a manger" to the painful description of the title relationship with the phrase "I'm just a station on your way, I know I'm not your lover." Mainly, Cohen's songs reflect the windswept melancholy of McCabe & Mrs. Miller, and the sense of dreams being built from the ground up, before getting crushed from above.

5. Eddie Vedder, Into The Wild (2007)

Much like Leonard Cohen's songs in McCabe & Mrs. Miller, the paeans to travel and freedom that Eddie Vedder wrote and recorded for Sean Penn's Into The Wild have been criticized for being too on-the-nose and too drippy. But that's precisely what makes them work. The actual life and death of driven young nature-lover Christopher McCandless can be interpreted a number of different ways—and was, in Jon Krakauer's more even-handed non-fiction bestseller—but Penn focuses on McCandless' boyish spirit of rebellion and restlessness, and his movie is a throwback to the sensual look and romantic vibe of early-'70s youthsploitation. In that context, Vedder's earnestness fits precisely, because Penn's Into The Wild puts its heart on its sleeve, and lets it bleed.

6. Alan Price, O Lucky Man! (1973)

It's no insult to say that Lindsay Anderson's epic follow-up to If…. flies off the rails early and often: What begins as an irreverent capitalist satire springboards deliriously into every conceivable aspect of British life, with each vignette more surreal than the last. Perhaps realizing that three hours worth of detours, no matter how brilliant, would likely exhaust even the most adventurous audience, Anderson commissioned Alan Price, formerly of The Animals, to write songs for the film. What's more, the songs are included as concert interludes within the movie, with Price and his bandmates knocking them out in a studio. These sequences help tie the extremely loose-knit narrative strands together, and are some of the film's most dynamic segments.

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7. Jonathan Richman, There's Something About Mary (1998)

The Farrelly brothers are regarded as pioneers of the gross-out comedy, but the secret to their success—something that unsavory facsimiles like Say It Isn't So and Tomcats never got—is that they're genuinely good-natured and whimsical at heart. Still, the Farrellys pulled off a tough balancing act with There's Something About Mary, which had to charm as a romantic comedy while offering extended lowbrow setpieces on natural "hair gel" and a guy getting his scrotum caught in a zipper. To that end, they did well to bring in Modern Lovers' Jonathan Richman as a one-man Greek chorus who pops in occasionally with his acoustic guitar to comment on the action. Typical of Richman, the songs are tongue-in-cheek and frequently hilarious, but they have a tone that gently serenades the romance, too, and makes the film's nastier bits go down that much easier.

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8. Seu Jorge, The Life Aquatic With Steve Zissou (2004)

Like Jonathan Richman in There's Something About Mary, Brazilian singer Seu Jorge drifts through Wes Anderson's tragicomic adventure as a one-man Greek chorus. Rather than commenting directly on the action, Jorge simply sings covers of David Bowie classics that don't really have anything to do with what's happening onscreen, but fit well anyway. Sometimes Jorge's Portuguese takes liberties with the lyrics: "Five Years" shifts from a tale of looming apocalypse to a tale of romantic longing and transoceanic travel. But Bowie didn't mind, telling cokemachineglow.com in 2006 that Jorge "paid equal tribute to both myself and [his] own formidable abilities."

9. Metallica, Paradise Lost: The Child Murders At Robin Hood Hills (1996)

As the music of Metallica plays throughout Joe Berlinger and Bruce Sinofsky's stunning true-crime documentary, it serves multiple purposes, simultaneously setting an appropriately dark tone for its examination of a triple homicide and its aftermath, and establishing the culture clash that led to a shocking miscarriage of justice. After the gruesome murder and mutilation of three 8-year-old boys in West Memphis, Arkansas, a small community pinned the crime on a trio of teenage outcasts, alleging that they were carrying out a Satanic ritual. Berlinger and Sinofsky contend—here and in their follow-up, Paradise Lost 2: Revelations—that the "West Memphis Three" were convenient targets, railroaded through the system on a dubious confession coerced from a kid with a 74 IQ. Caught up in all the hysteria, their supposed ringleader, Damien Echols, was damned simply for standing out as a goth kid who dressed in black, wore his hair long, and listened to Metallica. The band's ironic presence on the Paradise Lost soundtrack blackens the mood and makes everyone culpable in this ongoing injustice.

10. Apocalyptica, Your Friends & Neighbors (1998)

The empty lives of bored intellectual elites residing in the anonymous urban any-city of Neil LaBute's Your Friends & Neighbors are laid bare with practically zero music. The "soundtrack" here is mostly the long silences of eventless days spent pining for another start, far away from the friends and spouses who have stalled their long-ago dreams. But brief spurts of Metallica, performed by cello quartet Apocalyptica, frame the big picture. As the opening credits roll following a brief prologue, we hear the lower register of "Enter Sandman" as it's bowed with vigorous menace, setting the stage much like a pit orchestra would, announcing the approach of something grim. The metal band's sitar-based slow-burner "Wherever I May Roam" gets the cello treatment at the story's close, leaving the unraveled lives of the film's characters with an appropriate coda. (There's also some sporadic use of their version of "Welcome Home (Sanitarium).") Why Metallica in an understated talkie about sparring couples? And why Metallica as played by cellists from Finland? Maybe because beneath the thin veneer of social mores and our efforts to be polite, we're just masking the monster within us all—like classical battling with metal. Or maybe it just sounds cool.

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11. AC/DC, Maximum Overdrive (1986)

Stephen King's lone directorial effort was never meant to be more than a loud, dopey movie about trucks crashing into stuff, and King underlined his intentions by filling the soundtrack with AC/DC's sublimely crude hard rock. The Aussie boogie-metal legends provide a couple of instrumental bridges and the thrilling new thudder "Who Made Who"—a song about men and machines, inspired by King's story of sentient vehicles enslaving their former masters—but most of King's AC/DC selections consist of well-known anthems like "You Shook Me All Night Long," "Hells Bells," and "For Those About To Rock." Because in the world of Maximum Overdrive, obviousness is a virtue.

12. Slayer, River's Edge (1986)

As if the image of a murdered teenage girl and her indifferent stoner boyfriend/killer weren't unnerving enough—"She was talking shit," the boyfriend helpfully explains—this grungy cult favorite ups the menace level with a soundtrack culled from specialty label Metal Blade. When a group of downscale suburban kids drive around and debate whether their loyalty is to their friend or to some higher moral law, the speed-metal riffage of Slayer blasts away on the car stereo, perhaps clouding their judgment. Or at least making it harder to hear themselves think.

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13. Wang Chung, To Live And Die In L.A. (1985)

William Friedkin's Oscar-winning classic The French Connection brought documentary-style realism to the American crime-movie procedural, evoking the gritty streets of New York City with handheld camerawork and authentically unsavory characters on both sides of the law. For his unofficial sequel, To Live And Die In L.A., Friedkin similarly captured a specific time and place by embracing the glitz and artifice of Southern California with the same vigor he brought to the sleaze and grime of early-'70s Brooklyn. Complementing the film's air of misplaced morality and detached debauchery is the atmospherically poppy score by Wang Chung, a synth group whose legacy will forever be tied to that "Everybody Wang Chung tonight!" song. The songs today sound hopelessly dated, but this actually plays to the film's benefit: To Live And Die In L.A. is unmistakably an '80s movie, with an insatiable need for "More! Now!" motivating the villains as well as the heroes. And what's a better soundtrack for that than a bunch of really catchy pop songs promising instant gratification?

14. Badly Drawn Boy, About A Boy (2002)

One of the knocks on Badly Drawn Boy (Damon Gough) is that his albums are long on musical ideas and short on cohesion, which may be why Gough's soundtrack for the Nick Hornby adaptation About A Boy ranks among his best work. Given the assignment to write songs and instrumental bridges around a single subject, Gough keyed into the mind of a sweet, precocious, outcast kid with no friends, an overbearing mother, and a general obliviousness to the things other teenagers find important. The result is bright and winning, from the charmingly buoyant "Something To Talk About" to deeper tracks like "Silent Sigh," which floats on a Peanuts-esque melancholy piano line, and "A Minor Incident," a direct, moving appeal from a boy to his screwed-up mom. Like the best entries on this list, the soundtrack is sewn into the movie's fabric, and it tells a story in itself.

15. Elliott Smith, Good Will Hunting (1997)

Danny Elfman provides much of the background music for Gus Van Sant's crossover hit (a.k.a. the film that launched Matt Damon and Ben Affleck), but Van Sant's Portland pal Elliott Smith dominates the emotional foreground. Key transitional scenes play to some of Smith's most resonant songs: "No Name #3," "Angeles," and "Say Yes" are allowed to stretch out, rather than be completely truncated. Then there's "Miss Misery," which netted Smith an Oscar nomination for Best Original Song—it plays over the big reveal and end credits, lending the whole enterprise an air of respectability. As for the movie itself, sure, it's a little hokey and filled with Robin Williams, but it's still a hundred times more resonant than Jersey Girl.

16. The Polyphonic Spree, Thumbsucker (2005)

When director Mike Mills wanted music for his debut Thumbsucker, he had two things in mind: Harold & Maude and Elliott Smith. Smith was to be to Thumbsucker what Cat Stevens was to Harold & Maude: the sole songwriter to propel the film forward with folk-based pop songs. Mills showed him an early cut, and Smith began working on music, even covering Stevens' "Trouble." After Smith's death in 2003, Mills ended up working with Tim DeLaughter and his band The Polyphonic Spree. It isn't hard to imagine what a full soundtrack of Smith tunes would have done to the mood of this film (Smith's version of "Trouble" is prominently placed), but The Polyphonic Spree's choral pop works well with the hazy malaise and suburban yearning of Mills' coming-of-age film. The Spree has always carefully ridden that fine line between cheese and glee, with the adult DeLaughter sometimes giving in too much to his inner child as a songwriter. Considering Justin, played by Lou Pucci, is a senior in high school and can't stop sucking his thumb, the two make a good match, in spite of the tragedy that brought them together.

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17. Tom Petty, She's The One (1996)

The one good decision writer-director-star Ed Burns made regarding the follow-up to his overpraised debut The Brother McMullen was to ask Tom Petty—fresh off the great Wildflowers—to do the soundtrack. Now if only Burns had found somebody more qualified to write, shoot, and star in his magnum opus! As it is, Petty's soundtrack more than holds on its own as a stand-alone album, offering more insight into romantic relationships on rough and ragged pop songs like "Walls" and "Hope You Never" than Burns musters in 96 minutes of celluloid. On Petty's expert cover of Beck's "Asshole," he achieves the tricky mix of humor and pathos Burns reaches for but doesn't have the depth to realize. The movie that plays in your head while listening to Petty's She's The One is probably more resonant than the one that made it to the screen.

18. Spoon, Stranger Than Fiction (2006)

Although Britt Daniel of Spoon only provides one new song, three old ones, and a few instrumental cues to director Marc Forster and writer Zach Helm's postmodern comedy, his music threads throughout the film, matched to a set of rhythmic new-wave classics. The movie takes a few too many cutesy turns, but Daniel's peppy minimalism carries a lot of the sentiment and drive that Forster and Helm fail to shoulder. Stranger Than Fiction is about uptight, routine-bound people learning to reorder their lives, and Spoon's casual fragmenting of rigid rock and soul song structures tells that story on its own.

19. Prince, Batman (1989)

It's safe to assume that the Batman soundtrack is nobody's favorite Prince album, but it nevertheless qualifies as one of the more fascinating creative detours in a career full of them. The infectious funk anthem "Partyman" adds an additional element of brash braggadocio to the Joker gang's defilement of the Gotham City art museum, in addition to serving as the perfect accompaniment to the self-parody stage of Jack Nicholson's career. The first single, "Batdance," is one of the weirdest singles ever to hit the pop charts, a funk-dance powered by an army of samples, many of them soundbites from the film. The Batman soundtrack later found a strange pop-culture second life in Shaun Of The Dead, when Simon Pegg and Nick Frost decided to hurl it at zombies rather than waste Sign O' The Times or Purple Rain.

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