While there were some very funny moments in the movie (quite possibly the best of which only made the DVD extras — a scene shot almost completely in the dark involving a fake vibrator), little stands out about it. Though there's a slightly unique angle where one of the main characters is a wine connoisseur, the story falls into this non-outstanding category. Two guys go off on a road trip to celebrate the end of bachelorhood of the one guy who is getting married.
The main characters, Miles (Paul Giamatti) and Jack (Thomas Haden Church), do come of as very real, which may not be the compliment you'd expect. In fact, my first impression of these guys was that they fit right in with my brother's group — a bunch of guys playing grown up, when all they really want to do is hang out, specifically with each other, play golf, drink, and talk about getting laid. Jack never really exceeds these low expectations, screwing around the week before his wedding and lying for the "uncool" Miles in an attempt to get him into the act.
Sideways is ultimately Miles' story, which saves the film for me. A writer waiting anxiously to find out if his latest effort will finally make him a published author, Miles offered plenty for me to relate to. (The only problem there is that I'm a writer that's never even gotten that far, and I'm not sure the character works for anyone that hasn't stared at a blinking cursor in an attempt to write.) He's a tortured sole who realizes his life is nothing like he'd like it to be, but holds on to his fun side by staying close to Jack. Though I could have dealt with more on Miles, an odd scene where he steals from his mother was a weak effort to delve into his dark side. In the end, I was surprised to truly care about what happened to Miles.
One of the funniest parts of the movie is Miles' effort to retrieve the wedding rings Jack has left at his latest one-night stands' place . . . after hubby came home. A scene on the golf course when others try to play through and, possibly the funniest moment that actually made the cut, a failed attempt to purposely crash Miles' car into a tree, keep the film in the comedy section with little argument.
An ending that was cleaner than expected — too clean, in fact — left Sideways as a movie that is just entertaining.