These movies all are about people who make music. This makes them musicals of a sort, but what make them interesting to me is that they examine the creative process. Rent away!
1. Hustle and Flow: Being a lo-fi home recording artist myself, I am always skeptical when anyone tries to depict the creative process that goes into recording a song. If you are a music fan of any of the legions of performers who have released recordings that they did at home, I suggest you watch this movie. It will give you keen insight into the highs and lows of lo-fi. My parents even loved it. And I guarantee you they don't listen to gangster rap in their spare time.
2. That Thing You Do: Maybe it is the sight of dewy Liv Tyler cheering the boys on in a succession of 60's outfits; maybe it is the fact that Tom Hanks wrote some songs for his pet project; maybe it is the unadulterated joy that the group gets when they hear themselves on the radio for the first time and dance around the drummer's dad's appliance store; maybe it's Steve Zahn; I don't know what IT is, but That Thing You Do has it. Did I already mention the dewy Liv Tyler? Well, she's Liv Tyler and she is DEWY.
3. Tenacious D: The Pick of Destiny: I am tempted to put this first on my list because I can't stop watching it right now. And when I say I can't stop watching it, I mean that I have watched it almost every day since I bought it 3 weeks ago. I am not kidding. Trying to write a FUNNY song that also rocks hard enough to be a legitimate rock song doesn't seem impossible in their hands. Each song is tasty, ridiculous, hilarious, and catchy-as-Dave-Grohl-in-hell. Seriously, give this one a chance. I don't know if I can be completely objective and I might be one of the people who drank the Kool Aid, but I can't imagine anyone not getting a kick out of this movie. And yes, I just did some sort of weird triple-negative thing that I can't explain. Jack Black and Kyle Gass are rock AND comedy gods in an unholy alliance of tune-age and laughs.
4. Prince: Sign o' the Times: Everyone knows Purple Rain. I'll write about it later on down the list. But this is the one to see. Why? Well, for one thing, we don't have to watch the pure hilarity of Prince acting. Seriously, he and Madonna should do a movie together. I think the whole medium of film might implode into the ether at the badness. No, this is a CONCERT film. But not your ordinary concert film. It doesn't have that back-of-the-arena after thought feel of most concert films. It has a gorgeous visual style and lavishes the viewer with treats. And then there are the songs. He does a medley of his old hits but for the most part the film goes song by song through the double album 'Sign o' the Times'. Sure he's a weirdo. Sure he's a demagogue. Sure he thinks he's the only one who ever had a sexual fantasy. But man can he give a concert.
5. 32 Short Films About Glenn Gould: I can't even remember anything about this movie except that I can't recommend it enough. Glenn Gould is a kooky Canadian concert pianist who rocketed to international acclaim very early in his career and then spent decades defying expectations. The film doesn't have anything to do with any of that, but I can't remember what it is about. Watch it.
6. Purple Rain: I just wrote about Prince right above so I'm bored with it already. Great movie though. I always wondered how small that motorcycle was in real life. Like, was it a Matchbox motorcycle? Was it a moped with a Halloween costume on?
7. Come Feel Me Tremble: Paul Westerberg's weird-ass home movie of his tour/recording sessions for the album of the same name. He asked for fans to send in footage they'd shot at his solo tour of 2002. He toured without a band for the first time ever and stayed behind after almost every show to sign autographs and chat with his longtime fans. It didn't make any headlines, but this was something akin to the Grinch cutting the Christmas ham. The live footage is interspersed with stuff he shot in his basement while recording. Seriously, this is a WEIRD movie. But awesome.
8. Don't Look Back: D.A. Pennebaker's awesome documentary about Dylan in London. This should probably be at the top of the list because if you watch it, it is supremely disconcerting. You know it was shot in the '60's but it is so MODERN feeling that none of the movies from 1-7 would be possible without this one. (Well, Tenacious D would be possible but you catch my drift!) You forget that Dylan was young, tough, and crazy until you see this flick. And you'll forever be glad that he dumped Joan Baez. He's smoking cigarettes and drinking coffee and she's strumming some stupid folk song in the background trying to steal the spotlight. You want her to shut up so you can watch Dylan type.
9. Amadeus: Somehow this movie gets us inside Mozart's head. It makes a rock star out of him and forces us to deal with him in the way we deal with superstars of our day. The genius of this is placing Salieri right there along with him...this contextualizes him so that we see him more clearly. Imagine a movie about, say, Bruce Springsteen in which John Cougar Mellencamp must constantly compare 'Pink Houses' to 'Born in the USA'. Poor Jonny Cougar!
10. This is Spinal Tap: I won't even go into it. Don't even talk about it. We all understand so let's just...shhh.
If you watch these movies back to back it will be a full day of joy.