Review in a Hurry: Writer-director-producer extraordinaire James L. Brooks (Terms of Endearment, Broadcast News) knows more about smart comedy than almost anyone on Earth. Lately, however, he seems to have wandered off (Spanglish).
The Bigger Picture: Washington, D.C. dweller, George (Rudd) is in a downward spiral. He's being indicted by the federal government for fraud. He's got a sneaky suspicion that the real culprit is the owner of the company, who is also his father (Nicholson). And his girlfriend just dumped him.
Freaked out and confused, he meets the lovely Lisa, played by Witherspoon, who seems just as confused as him.
Lisa's a professional softball overachiever and has been cut from the team. As an actress, Witherspoon's best with roles like this—slowly losing control (Election) and surviving embarrassing situations in a hilarious fashion.
Since this is a Brooks' rom-com, George and Lisa are in a permanent state of overexamination: about their careers, about their significant others and mostly, about themselves. Are they too smart for their own good? Maybe.
The third wheel of the inevitable love triangle isn't burdened with being an intellectual. Matty's (Wilson) a $14-million-a-year pitcher who shoots from the hip and is the nicest narcissist to grace the big screen in years. (After Lisa sleeps over at his awesome pad he insists she takes from his special closet, filled with casual "babe" wear in sizes S to XS.)
The refreshing thing about the How Do You Know is Lisa is being wooed by two decent guys. One of Brooks' strengths as a writer has been his insistence that even if there's a shallow character (like Wilson) they remain incredibly likable.
So the cast is great.
The problem is that for most of the running time, How Do You Know meanders and has a hard time finding the right tone, lurching forward from one scene to the next. There are some classic Brooks exchanges—George and his dad quip about whether cynicism is sanity or optimism is—but too many moments underwhelm.
The problem is that there really isn't any chemistry between the performers (a strange feat considering all three leads are incredibly charismatic.)
Brooks takes years developing ideas for his films, and while the premise of How Do You Know is solid, a less mannered approach would have helped. Comedy that is too studied, too clever can be suffocating.
The 180—a Second Opinion: Fans of Reese will still delight; she's just as good as ever, really shining in the role. And with the cinematography by Stephen Spielberg's main cinematographer, Januz Kaminski, Reese and Washington, D.C. look gorgeous.