Most of the criticisms you've heard of Ang Lee's Taking Woodstock are pretty apt. Yes, it feels very slight. Yes, the main character is less interesting than most of the supporting characters. Yes, it's just a little odd to make a film about Woodstock without a single shot of the performers on stage. Even so, I'd give it a marginal recommendation. It's ultimately so generally sweet and likeable that it's hard to hold much of a grudge against its many failings.
Lee is interested in the organization of the festival, the story of Elliot (Demetri Martin), a young Jewish man helping his parents run a fast-fading New York "resort," who takes advantage of a neighboring town's intitial cancellation of the festival and joins forces with local farmer Max Yasgur (Eugene Levy, unusually subdued) to unexpectedly bring 500,000 hippies out for three days of peace, love, and music. Elliot is a more-or-less closeted homosexual, and Lee wants to find in his coming-out story a parallel with the sexual liberation of the era (what's happening on stage is far less important, the film suggests, than what is happening in the audience, although of course the music does play a big role in the era's liberation, which doesn't get adequately addressed here). Elliot's story never feels particularly alive to me, and the film works best in funny and touching individual scenes. I particularly like the recurring bits with the Earthlight Players, a theatrical troupe Elliot houses in his barn, and a scene near the end where Emile Hirsch, as a mentally-addled Vietnam vet, experiences a remarkable moment of clarity at the festival, getting back in touch with the childhood that the war took away from him (somewhere Beth is saying: "But does he get naked?").
Woodstock plays less subtly than other collaborations between Lee and his constant screenwriter James Schamus, such as The Ice Storm and Brokeback Mountain. Perhaps that's appropriate to an era known for its politics and protests, but various speeches seem to oversell the idea that Woodstock was American culture's last gasp of innocence. Still, there are moments that play a bit more subtly in hinting at darker things to come. In a bit that plays almost as a winking aside to its contemporary viewing audience, Yasgur remarks on how the festival is becoming commodified even as it happens (locals are trying to sell bottled water for a dollar, he remarks, incredulous). And the film's final moment is nice too, with festival promoter Michael Lang vowing to do a "totally free" Stones concert in California. Here, Lee and Schamus trust their audience to understand the Altamount reference, and the final image leaves us with an ominous feeling as the camera lingers on the wreckage left in Yasgur's field after the crowds depart.