While it's true that James L. Brooks may have had more success in both television and movies than any other writer/producer/director in the last four decades, it's also fair to say that his recent output hasn't come close to matching his initial cinematic efforts. Terms of Endearment and Broadcast News were as good a one-two punch as just about any filmmaker could hope for, displaying an uncanny knack for bringing his smart, character-based sitcom style to the big screen. How Do You Know, a romantic comedy starring Reese Witherspoon, Paul Rudd, and Owen Wilson, isn't anywhere near as good as Brooks' best, but it's much more enjoyable than anything he's done since those early masterworks.
Lisa (Witherspoon) devoted her life to playing softball, and has become the most beloved player on the U.S. national team -- but a new coach decides she's too old and too slow and cuts her. With unexpected free time on her hands, she finds herself in a relationship with Matty (Wilson), a fun-loving big-league pitcher whose idea of being a good guy involves keeping a stash of pink sweat suits in his apartment so that his various female conquests can avoid an unflattering walk of shame the next morning. However, Matty isn't the only new guy in Lisa's life. There's also George (Rudd), a businessman who recently discovered that the government may put him behind bars for his company's unethical dealings. Lisa finds herself emotionally drawn to the inherently sweet George, even as she deepens her commitment to the possibly maturing Matty.
The pleasures in How Do You Know are all in the acting, particularly by Owen Wilson, who hasn't been this outright enjoyable since his cameo in Meet the Parents. The character could easily be nothing more than a collection of the most tired jock stereotypes -- the testosterone-laden meathead whose fame allows his narcissism to metastasize -- but Wilson is so boyishly charming, and his comic timing so honed, that Matty stays thoroughly likable even when he's at his most infuriating.
In fact, likable is what Brooks does best at this point in his career, and with that in mind, it's amazing that it has taken this long for him to work with Paul Rudd, an actor so modestly charming that he can hold a picture together just through the sheer force of goodwill. Brooks takes our sympathies with Rudd to the breaking point, though -- George is such a nice guy that his neuroses are supposed to seem endearing when in fact they're annoying. Witherspoon is also a performer capable of charming audiences, and she pulls off her role with aplomb, bringing out the generally strong-willed Lisa's newfound insecurities with such ease that it's understandable why she stays with Matty even though she knows he's not the right guy for her. Still, it's hard to shake the feeling that the character is little more than a variation on Holly Hunter's Type-A firebrand from Broadcast News. In addition, Brooks' longtime cinematic collaborator Jack Nicholson shows up as George's morally compromised father, delivering an F-bomb-laden tirade that initially earned the film an R rating until cooler heads prevailed (the MPAA probably discovered their funny bone). And Kathryn Hahn savors every morsel of dialogue she gets as George's loyal secretary.
At one point, Brooks was one of the finest screenwriters in Hollywood, but in recent years he's become one of its finest overwriters -- every character in the movie talks too much, and is too quick to talk about how he or she feels. However, that's not entirely a bad thing, since Brooks can still whip up massive amounts of often-humorous dialogue, and he's a secure enough director to let his actors make the laughs come from the characters and not the situations. It's easy to follow these characters along for the ride, even if you're not going to end up any place all that special.