It may be a lighthearted comedy about vacation-going, but it's actually a rather clever comedy about self-discovery, learning to love and so forth through the magic of vacation-going. Though the premise may sound incredibly plain in other ways (two ladies decide to live in each other's houses for aforementioned getaway trips), it becomes far more intriguing than that.
Chirpy Cameron Diaz finds what you may call typical Hollywood love when her characters runs into meek Jude Law, but spectator would actually be surprised to discover the film's twist that Law is really a single dad with two kids with barely enough time to be the typical playboy. Against type Kate Winslet, who always does a great job in films, doesn't find cinematic love as quickly. She instead finds friendship in an old Hollywood film screenwriter played by the great Eli Wallach (Clint Eastwood's troubled, but entertaining partner in Sergio Leone's 1966 Man With No Name classic, The Good, the Bad, and the Ugly; he recently had a small cameo in Eastwood's 2003 film of Mystic River). A guy who talks about why Hollywood films today stink because of bad writing. Huh, that's different.
Bombastic comic Jack Black plays a cooky, awkward music composer trying to hook up with Kate, but their relationship is grounded in a cautious reality. Diaz's character is designed to be quick on the rebound, but Winslet and Black are the types who make friendship their first stepping stone. A fanboy spectator will notice the really funny reference when this nerdy couple set foot in a soon-to-be-obsolete video store where he is singing/humming famous themes from classic films. Silly fun that may be labeled as a chick flick, but this film still doesn't fit a usual norm.