Since they started putting out movie song compilations, generations have been measuring their lives and loves with soundtracks. You could say the soulfully dissatisfied ’60s were heard through Simon and Garfunkel’s tunes in The Graduate. The ’70s were all about the sexy disco strut of Saturday Night Fever, while the go-to ’80s became the energetic pop of Fast Times At Ridgemont High, all before the ’90s came soulfully down to Earth with Jerry Maguire. Now, if the growing indie hit (500) Days of Summer is any indication, we’ll be closing out this decade with this infectious alt. rock tribute to the charms and woes of love, which goes full circle with a Simon and Garfunkel tune to boot.

But then why do song compilations stick with us like Summer in the first place? They’re certainly not like the music marketing department collection designed to push the studio label’s latest bland sensations, because here, the directors and music supervisors really give a hoot that they’ll find songs that actually say something that the characters can’t – whether it’s Dustin Hoffman’s rebellion against the status quo, the sexed-up energy of California dreamers, or, in this case, a guy’s preposterous romantic dreams derived from watching pop culture’s representation of perfect love, only to discover it’s bullshit. Yet it’s a nice trip to get to that realization — a journey that the catchy songs on (500) Days of Summer takes us to with their indie street cred and movie artistry intact.

But then, the song-driven success of (500) Days of Summer is due, no doubt, to music video vet-turned-director Marc Webb, who seems to have created the film from the songs up. Here characters are constantly listening to music on their iPods, stereos, at Karaoke bars, or cruising in record stores – the sum collection of musical hipness around them turned into the soundtrack of their lives. For the most part, Webber is smart enough to play the songs straight up, using lyrics instead of spoken dialogue to drive home his perceptive points.

If there’s a theme to Summer, then it’s Tom’s love of “sad British pop music,” a gloomily beautiful English beat that’s summed up by The Smiths, whose “There Is a Light That Never Goes Out” has such strongly impacting lyrics like “Let me get what I want this time.” Here they stand in for the romantic dreams and resulting anguish of card-writer-come-architect Tom Hansen, who gets taken for a 500-day ride when he falls for the free-spirited man-crusher Summer Finn. Further kicking in this theme is a coffeehouse-ready version of the song by She & Him, which bookends this soundtrack’s tuneful irony.

Sure, it’s one thing to listen to all the noodlings playing at Starbucks and then trying to create some soundtrack out of them, but the artist choices in (500) Days of Summer manage to be both post-Gen X hip and emotionally meaningful at the same time. Indie darling Regina Spektor is featured twice, as her rapid pianos and violins build a statue of “Us,” desperately unfolding the lead’s hoped-for relationship like it’s coming from the wish list of a besmitten 12-year-old. Her “Hero” deals with what happens when it all goes to hell, repeatedly telling the despondent Tom that “It’s All Right.”

With its time-jumping structure creating a mood that’s joyful at one moment, then wrist-slashing ready at the next, (500) Days of Summer’s emotional roller coaster is beautifully engineered from start to finish. The ska guitar energy of The Black Lips’ “Bad Kids,” the engaging strut of The Doves’ “There Goes the Fear” and The Tender Trap’s U2-like guitar strumming of “Sweet Disposition” all have great montage-ready rhythms. Mumm-Ra’s “She’s Got You High” does much to promise Tom’s hopes of winning back Summer yet has a melancholy bite that promises he’ll be further f’d up by her. Then there are outrightly cute bits with the retro keyboard ballad of Meaghan Smith’s “Here Comes Your Man,” it’s off-kilter chorus sounding off with “So long, so long.” And what romantic compilation wouldn’t be complete without a French song, with Carla Bruni’s “Quelqu’ un M’a Dit” (translation: “Someone Told Me”), which becomes the equivalent of a mime for the beyond-irritated Tom.

When those old chestnuts show up here, they go way beyond the hip factor of playing your granddad’s greatest hits. For Summer’s “big” dance sequence, having Tom swivel to Hall & Oates’ “You Make My Dreams” is brilliant beyond anything you’d see in the oh-so-ironic likes of Moulin Rouge, for you can imagine that Tom was infected by Hall & Oates’ bubblegum delight since he was a kid (a retro idea brilliantly complemented by having Tom see his reflection as Han Solo). He’s so filled with joie de vie after first scoring with Summer that why wouldn’t everyone would join in the dance with him? But then, what great scores in life aren’t accompanied by a song from the ’70s or ’80s? When Summer starts bawling to Simon and Garfunkel’s “Bookends,” it’s a full circle to her love of The Graduate (even though this song wasn’t in it). She realizes that the song’s “Time of Innocence” isn’t going to happen for her and Tom — at least in her opinion — and perhaps no song could better sum up the disconnect between movies, TV and songs’ version of romantic love and the real thing. Even though we’re still watching a movie version of it in the end, (500) Days of Summer stands as one of the most honest and truthful depictions of a relationship to ever appear on film.

If there’s one thing to get the short end of the soundtrack stick in a song-filled movie, it’s the score. Special mention should be given to the one in Summer by Mychael Danna and Rob Simonsen, whose perkily ironic and subtly lush score serves to compliment and contrast the tunes on hand, and does as much of a great job in selling us a couple that could never be. Though you hear a bit of their score under the whistling, opening narration of “A Story of Boy Meets Girl,” the sleeper success of Summer could hopefully inspire a release of Danna and Simonsen’s score on its own.

Of all the big soundtracks that have summed up moviegoers’ lives and loves, (500) Days of Summer might derive from the smallest-scaled picture to be included in that group. But in the overall thought and emotion that’s been given to having its songs sum up real-world experiences, Summer proves to be one of the most successful. You tap your toes to it as Tom’s heart gets broken, and then reset from one scene to the next, the artists speaking for him when he’d just rather pull the covers over his head. Better yet, it gives you the catchy feel that love goes on — at least in the movies.