Sandwiched somewhere between the American Spirit commercials and the Clinton campaigning that make up Definitely, Maybe is a surprisingly rewarding romantic comedy — one worth the effort, because some effort's actually been put into it. Imagine, really, old-school Woody Allen starring that shit-eating smirker from Van Wilder, Ryan Reynolds, who's always been something of a slumming comer 'til now. If this isn't exactly Annie Hall or Manhattan, the mere fact that it aspires to those heights is worth a celebration of some kind — say, a small street fair in Hoboken?
Such are the diminished expectations caused by living in so depressed an era in studio cinema-making that Kate Hudson and Matthew McConaughey only last week got another shot at falling in big-screen love, ugh. Happily, this is no fool's gold, but something a little more valuable: a romantic comedy in which the love story's plenty dinged-up with disappointment and the requisite laughs are played instead for sad, knowing grins. The movie even dares to suggest that happy endings come to an end — something rarely acknowledged in studio movies peddling the sickly sweet promise of Everlasting True Love on Valentine's Day. Definitely, Maybe doesn't quite possess the courage of its convictions — not to ruin anything — but it also digs deeper than your average romping rom-com and is populated by some very sad and lonely people who keep bumping into each other in New York City.
The film's told almost entirely in flashback — during that long-lost decade of the 1990s. Reynolds, of course, looks very much the same in any decade: When first we meet him in 2008, he's a corner-office ad exec being served his final divorce papers. Smartly capturing the ease with which we disconnect from the outside world, he slaps on his iPod, punches up Sly and the Family Stone's "Everyday People," and struts through a silent Manhattan — a dude living his own movie, scored to his perfect song. He then picks up his daughter Maya (Abigail Breslin), who turns out to be one of those 11-year-olds in movies who sound like their 51-year-old writer-directors (Adam Brooks, in this case) when discussing things like love, sex, and relationships.
Maya wants to know how it all went wrong between her parents, and as a begrudging bedtime tale, Will lays it out for her, changing the names of the women in his life story in order to keep his daughter (and the audience) guessing Mom's identity. (Sounds like a very special episode of How I Divorced Your Mother.) As Will recounts his life in New York in the early to mid-'90s, he encounters several women with whom he will fall in and out of love — one of whom will become his wife and Maya's mother. Only, at the end of Will's story, the parents will be divorced, and Maya will be left with what she calls "a romantic mystery" absent its fairy-tale finale.
But before the unhappy present-day, first to the promising yesterdays: It's 1992, and Will's a collegiate Young Democrat in Wisconsin dating the old-fashioned Emily (40-Year-Old Virgin's do-it-herselfer Elizabeth Banks). Emily refuses to move to New York, where Will's been hired to work on Bill Clinton's 1992 campaign — filling toilet-paper dispensers, it turns out. Working for Clinton, Will elects himself two best friends: Derek Luke's Russell, with whom Will eventually forms a political-consulting firm; and Isla Fisher's April, the freewheeling Xerox girl with the Smiths T-shirt who frowns on things like presidents and marriage. Also in New York: an old friend of Emily's named Summer (Rachel Weisz), a would-be writer shacked up with a cantankerous, decrepit, robe-wearing, chain-smoking, Scotch-drinking, pop-culture-loathing author-professor brilliantly named Hampton Roth, played by Kevin Kline. (Oh, would that the Roth character gets his own feature one day.)
And, over the course of the next couple of hours, Will and these bright, beautiful women keep crossing paths — as lovers, as disappointments, as friends, as what-coulda-beens, as what-might-bes. Brooks, whose French Kiss screenplay was as tony and old-fashioned a romance as Hollywood's made in 20 years, ultimately grounds the movie in the up-and-down everyday — in which yesterday's love affair is today's break-up is tomorrow's regret. As romantic and sweet and silly as the film can get — Weisz, out of nowhere, offers an unexpectedly touching, minor-key version of "I've Got a Crush On You" — ultimately it just shrugs and says, "Do your best, expect the worst, and you'll muddle through."
Of course, one could easily look at the movie as a well-timed portrait of one man's shattered affection for Bill Clinton — it encompasses his entire presidency, from the early Man From Hope love-in to Monica Lewinsky. Reynolds, muting his smart-ass qualities without dulling his timing, bemoans Clinton's parsing of words: "What happens when they give him a hard word?" he snaps at the TV as Clinton ponders the meaning of "is." Truth is, it's just an unexpected delight to find Reynolds in something resembling a grown-up comedy; he forever seemed destined to be the dude from Two Girls, a Guy and a Pizza Place. Maybe he's no longer a could-have-been, but rather a might-be-after-all.