I think the Wilco documentary by Sam Jones, I Am Trying to Break Your Heart, is magnificent, and was riveted from the first, even though I wasn't a Wilco fan at the time. As many on here probably know, the film begins more or less on the day they fire their original drummer, the very good Ken Coomer, and replace him with the fantastic Glenn Kotche, and follows the band as tensions grow between founder Jeff Tweedy and the guy who had increasingly become the band's creative sparkplug, Jay Bennett, including as the band gets suddenly dropped from its label.
Last year a new documentary came out, Where Are You, Jay Bennett?, which tells the story from a different POV and fills in many gaps. It's very well done, very interesting, and very moving. If you're at all a fan of the band, it's a fine use of your 100 minutes.
Also, here's director Sam Jones talking about the making of the I Am Trying to Break Your Heart film with Jason Sudeikis: