This is another one of those roundup list style posts wherein taste and subjectivity will vary wildly like a rabid dog, with one camp saying, are you kidding me? You included that? Or, WTF? You didn't include Pink Floyd's The Wall? Are you a freakin' zombie? But the truth is, these are among the best in my opinion, and I don't think I'll be alone here in listing these five, and I'll offer as a caveat that it was probably stupid in the first place to try to narrow it down to five, so the hell with it. Here's five. Don't like 'em? Make your own damn list next time.

1) Martin Scorsese's The Last Waltz
Whether or not you like the music is almost totally a non issue. So what if you've never painted a house and you have no idea how to appreciate "classic rock" which is pretty much besides the point. You know Bob Dillon. He trumps all musical styles. He's a friggin' icon for chrissakes. Anyway. When he finally put together a back up band after going electric, his band was called The Band. You should take that to mean exactly what it sounds like. So good, they should be referred to as The Band, as in, The Only Band. Anyway. They put together a final show after touring for nearly all their lives, and invited many of their friends and coincidentally also musical luminaries of the sixties and seventies to come up on stage and join them for a tune or two. <a href="http://www.imdb.com/title/tt0077838/">The Last Waltz</a> was filmed amazingly by Martin Scorsese. 1978. 117 minutes.
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2) Straight, No Chaser: Thelonius Monk
Jazz enthusiast or not, those cats from decades past were from another planet, and film absolutely loves them. Too bad you weren't around to visit a Harlem night club in the fifties or sixties, or even better, to have visited Paris to see some expatriates play to a crowd that was actually smart enough to try to understand what they were doing and maybe even appreciate it. Produced by Clint Eastwood of all people, this fine documentary is also (bit of trivia here), the <a href="http://www.mattybyloos.com/music/monk-straight-no-chaser-1988-ill-flip-ya/">origin of Fenster's line, I'll Flip Ya, I'll Flip Ya Fo Real</a>, from the movie which you probably are a fan of, The Usual Suspects. Shot in black and white, and totally compelling, based on the life and concerts of the jazz great, <a href="http://www.imdb.com/title/tt0098465/">Thelonius Monk</a>. 1988, released in 1990. 90 minutes.
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3) I Am Trying to Break Your Heart, Wilco
Some of you may not be fans, and some of you might not even have ever heard of Wilco. My guess is that a lot of you will know of them, maybe know only a bit about their music, but maybe never have seen this masterwork of cinematography. In this film, first-time filmmaker and award-winning photographer Sam Jones documents the recording of Wilco as they write, record and produce their album, "Yankee Hotel Foxtrot." In the process, singer Jeff Tweedy deals with vomiting and migraines, guitarist Jay Bennett pulls a diva move (open to interpretation) and quits the band, and the record company essentially backs out of the deal while handing the completed album, rights and all, back over to the band. A real story of musical beauty and creation, with, again, unreal film-making talent behind it. And literally some of the most gorgeous opening film credits ever put on to a screen. 
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