Sideways is actually "The Odd Couple" for the new century. It features two friends who are almost total opposites. Jack (very aptly named) is a shallow "good time charlie". He lives for the moment and has very few interests other than Sex, booze and golf. Myles is very cerebral and very knowledgeable, an English teacher, with a real appreciation for wine tasting right down to the smallest nuance. He is also very depressed about his recent divorce and has no idea when to "say when" in a relationship.
The premise is that Myles is going to take Jack for a last fling in the week before his wedding. Why Jack would want to have Myles take him is rather curious. Perhaps Jack and Myles have lost all their friends with their impusive behaviour and have been left with just themselves.
The pair head from Southern California over to the Napa Valley wine country where they sample wines and come across a couple of waitresses . Myles is careful and respecting of them, but Jack is ready to get a little action and wants Myles in on the deal. This is good for Myles. He is still hung up on his ex-wife and when he gets too much to drink , gives her unwanted phone calls.
Jack sets Myles up with Maya, a very smart lovely lady also versed in wine tasting and with a heart of gold. Jack finds Stephanie, an equally impulsive good time lady. The chemistry between all is good and for the rest of the movie their exploits with make you laugh and cry.
This movie is reminiscent of the situational movies of the 60s and 70s. Younger people raised on action movies and "chick flicks" may find it somewhat boring. I would say it was a breath of fresh air from todays pictures.
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