Back in the day: Rachel Weisz and Ryan Reynolds in the pre-iPod era of Definitely, Maybe (Photo: Universal Pictures)

For all its inconsistencies, ambitions and rom-com conventions, Definitely, Maybe made at least one good impression on me. But indulge a preface, if you will: Until I succumbed about two years ago, I swore I would never own or use an iPod. My reasoning was twofold, and more pragmatic than militant: New York offers too much that such artificial stimulus would compromise, and I never wanted to condition myself (or my attention span) to an inability to live in my own head longer than two or three minutes at a time. IPod converts swore I had it all wrong -- that the city's natural rhythms tightened and its melodies harmonized and one could consciously move inside it as opposed to subconsciously working against it. Maybe, I replied, but I preferred the grand, captivating dissonance of dialects and kinesis. (I also dreaded the oblivion I knew would get me run over by a cab, but that's no one's fault but mine.)

That all changed after a rainstorm in late winter 2006. I walked down East 86th Street at night listening to a borrowed iPod, seeing what there was to see. I didn't really know how to use it; the first song I heard was by the first artist on the playlist: "You Are My Sister," by Antony and the Johnsons. It was an elegiac selection for a romantic tableau: umbrella bustle through streetlight-orange mist, cars reflected on wet asphalt, sidewalks and scaffolding, standers-still and movers-on. It was a new way of viewing New York, except it wasn't, because really, this was a movie. Or rather, this was my movie, and it had a soundtrack.

I don't know if that's what my persuaders had in mind, but for better or worse, I don't go many places now without my iPod. Neither, I suspect, does Definitely, Maybe's lead character Will Hayes (played by Ryan Reynolds), an ad exec who accompanies his afternoon stroll to pick up his daughter (Abigail Breslin) from school in Tribeca with an earbud overture of his own. I've never seen anyone attempt to replicate this urban experience in a film before.

"I wanted to set the table," writer-director Adam Brooks told The Reeler in an interview last month. "This movie is a little bit of a valentine to New York City, and I'm always amazed how when you put your headphones on in the subway or in the streets it can change everything. You put the right track on and everything looks great. You put the wrong track on, and it's like this existential gloom where everybody's looking like they're sad. It's amazing how the city can look through the prism of that music."

Will's journey bears more than a few geographic implausibilities, but the split- screen depictions of frolic in Columbus Circle alongside sun-kissed SoHo, however postcard-y, are often the kinds of scenes subject to the most radical, revelatory iPod interpretations. Knowing this, Brooks initially tried Radiohead; it was too "spacy." Then he unsuccessfully tried jazz. U2 worked well, but he couldn't afford the rights clearance.

He moved on, preferring contemporary alternatives to balance out the "period" music of scenes set in 1992 (Nirvana, R.E.M. and even Vanessa Williams, whose hit "Save the Best for Last" Will fantastically characterizes as "an excellent cure for the will to live"). But this being a (studio) dramedy about 16 years in the romantic life of a sensitive, upper-middle-class white New Yorker facing divorce, single fatherhood and subordinated idealism, Brooks knew mood and tone required direct attention, and fast. Will's initial choice -- Imran Hanif's hip-hop screed "Bitch Face" -- gets about two seconds of track time before he retreats, almost shocked at himself. Then, Brooks told me, he found "the Sly song."

"He was one of my heroes as a teenager," the director said of Sly Stone, whose funky if saccharine (at least in this context) "Everyday People" ultimately provided the soundtrack to Will's own movie. "And it just worked, right away. There's kind of a bounce to it. And there's something kind of political in a naïve, lovely way that's so typical of Sly and the Family Stone. It's very generous and open and inclusive. The energy of it had to do with his walk, and it really made the hip-hop joke that we came up with work better as well as kind of an announcement of what kind of movie it is."

Whether the scene works for you or not likely depends less on the song choice, however, than whether you relate to the phenomenon and believe in Will's authentic experience. I'm there for the first half of that equation, but Reynolds' bemused observations -- epitomized by a constant half-smirk flirting with its own arrythmia -- are a tough sell. He didn't make it any easier for me on the press day, first specifying that "I don't think that was an iPod" before cavalierly acknowledging: "That's the modern world these days. I'll go on long-distance motorcycle rides and I'll have an iPod inside my helmet, which is not only unsafe, but illegal."

Nevertheless, Reynolds' admission alludes to a kind of inheritance conferred from the road tripper to the pedestrian -- an individual taste for sight and sound never more accessible and perhaps even necessary than it is today. Twelve-year-old Breslin, for example, lit up when asked about her own iPod. "Actually, I have a blue Nano that I got on this movie," she said, professing her love of the Jonas Brothers and Hannah Montana. "I listen to it all the time -- when I'm in my room, when I'm in the car. Usually when I'm in the car."

New mother Isla Fisher, who plays one of Reynolds' Definitely, Maybe love interests, was the lone exception among the film's principals. "I don't tend to use an iPod anymore, and basically the only thing on my iPod now is Baby Einstein and Beatles music for babies," she told The Reeler. "I just have it by the changing table."

Beatles music for babies? "You know," Fisher continued. "It's just all the great Beatles songs with a bad synthesizer. Apparently babies respond to music that sounds terrible." Call it an early-life soundtrack. The city will make them come around.