The only other film about Woodstock that I've seen was Michael Wadleigh's Woodstock documentary from 1970 (one year after the 1969 concert). Wadleigh captured the large scale that was necessary to convey the grand feelings that were circulating among the attendants during that very summer in the Catskills. Taking Woodstock's director Ang Lee takes a different approach by doing a more back-door examination of how the festival started and the movie is more about organizer Elliot Tiber (Demetri Martin in his first dramatic role) than it is about the festival. Unfortunately, it seems that one must use a large canvas if they really want to delve into the themes that Woodstock now represents in popular culture. The characters need to seem as grand as the events but instead Lee and screenwriter James Schamas decide to place the audience as a fly-on-the-wall and let moments (the concert itself) and flow by and the emotion (present in the characters) remain thinly veiled.
There is a huge ensemble of actors present in the film, but most of them feel like the equivalent of cameos. That is not to say that the variety of cast members are only limited to a few appearances, it is just that they come-and-go and we really only stay with the emotions that Elliot Tiber is experiencing. Imagine if Robert Altman (or even Paul Thomas Anderson) had handled a Woodstock movie? Altman was the master of these massive character studies and introduced his own narrative flow through the interconnectedness of the characters themselves (see MASH, Nashville, The Player, Short Cuts, Pret-A-Porter, and Gosford Park to know more about what I'm speaking of). I think Ang Lee could've pulled it off and I'm almost disappointed that he didn't take this opportunity to do something grand (just as a reminder, Ang Lee is a massively talented and I sometimes feel widely underrated director whose filmography includes The Wedding Banquet, Eat Drink Man Woman, The Ice Storm, Crouching Tiger Hidden Dragon, Brokeback Mountain, and Lust Caution). By just sticking with Tiber, we often miss out on the implied events that we hear about going around in the background. Perhaps if Tiber was placed alongside those events (and there a few very well shot and choreographed moments involving large crowds) maybe we would've came to a greater understanding about both Elliot and the themes from the festival itself.
Tiber is played by Martin as a shy boy who is still struggling with his sexuality. He often has to put up with his cranky parents (his mother is played by Imelda Stauton in a wildly enjoyable and different role compared to the ones I often see her in) but he is politically active enough that he pushes the idea of having a concert in the town of Bethel to the entire town hall. This leads to some interesting scenes between Tiber and Max Yasgur (Eugene Levy) who owns a nearby farm that Tiber wants to try to use as a part of the festival grounds. Perhaps it is because Levy and Martin are both comedians that of all the supporting characters, Yasgur appears to have the most interesting chemistry with Tiber. Yet it appears that Lee would rather have us take notice of Michael Lang (Jonathan Groff), the main Woodstock organizer. I actually found Groff to be annoying in his portrayal of Lang. Perhaps I was just uncomfortable at the sight of a bare chested hippie but Groff gives Lang this unwarranted and nearly overdone enthusiasm about practically everything. He gives a "wow" or "gosh" to just about every situation that arises while planning the concert.
The other character that I think people will find the most interesting and engaging would be Vilma (Liev Schreiber). Yet it is not because of Vilma's interactions with Elliot (as is the case with Yasgur) but instead Vilma just stands out thanks to Schreiber's convincing portrayal. The character is a former marine turned transvestite that is humorously hired for security. This leads to a few entertaining situations but there is one moment that I'd rather let viewers discover that speaks to his/her character in a very unique way. Even though the interaction between the Elliot and Vilma is not the most interesting, Vilma has a very important impact on how Tiber lives his life. Towards the end of the film, Tiber gives into his feelings and defies his parents while completely stepping out of the closet so that he can be at peace with himself. Yes, this goes along with the theme of peace that Woodstock brought about but I feel Lee still doesn't fully grasp the metaphor.
Like I said before, Lee is just not grand enough in his depiction of Woodstock. Although there are several other good performances (forgot to mention Jeffrey Dean Morgan, Emile Hirsch, and Paul Dano), the film is primarily a biopic about Elliot Tiber and his own personal struggle that would've been enhanced if Lee went the path of Wadleigh and actually used the concert itself as a perspective.