Taking Woodstock is a 2009 American comedy-drama film about the Woodstock Festival of 1969, directed by Ang Lee. The screenplay by James Schamus is based on the memoir Taking Woodstock: A True Story of a Riot, a Concert, and a Life by Elliot Tiber and Tom Monte.
Set in 1969, the film follows the true story of Elliot Tiber (Demetri Martin), an aspiring Greenwich Village interior designer whose parents, Jake (Henry Goodman) and Sonia (Imelda Staunton), own the small dilapidated El Monaco Motel in White Lake, in the town of Bethel, New York. A hippie theater troupe, The Earthlight Players, rents the barn, but can hardly pay any rent. Due to financial trouble, the motel may have to be closed, but Elliot pleads with the local bank not to foreclose on the mortgage and Sonia delivers a tirade about her struggles as a Russian refugee. The family is given until the end of the summer to pay up.
Elliot plans to hold a small musical festival, and has, for $1, obtained a permit from the town’s chamber of commerce (of which he is also the president). When he hears that the organizers of the Woodstock Festival face opposition against the originally planned location, he offers his permit and the motel accommodations to organizer Michael Lang (Jonathan Groff). A neighbor, Max Yasgur (Eugene Levy), provides his nearby farm land; first they agree on a fee of $5,000, but after realizing how many people will come, Yasgur demands $75,000, which the organizers reluctantly accept. Elliot comes to agreement about the fee for the motel more smoothly. Initial objections by his mother quickly disappear when she sees the cash paid in advance. A cross-dressing veteran, Vilma (Liev Schreiber), is hired as a security guard.
Elliot and Yasgur encounter a little bit of expected opposition. The local diner refuses to serve Elliot anymore, inspectors target the motel (and only his) for building code violations, and some local boys paint a swastika and hate words on the hotel. However, resistance quickly dissolves in the tidal wave of peace and love (and commerce) brought to the area. The Tiber family works hard serving the massive influx of visitors and become wealthy in the process. Elliot also struggles with hiding his homosexuality from his family, when he connects romantically with one of the event organizers staying at the motel.
On the first day of the concert, Elliot, his father, and Vilma hear the music begin in the distance. Elliot’s father, transformed and enlivened by all the new life in town, tells Elliot to go and see the concert. Elliot hitches a ride through the peaceful traffic jam on the back of a benevolent state trooper’s motorcycle and arrives at the event. There, he meets a hippie couple (Paul Dano and Kelli Garner), who invite him to join them on an LSD trip in their VW Bus a short distance from the crowd. Elliot has trouble relaxing at first, but gradually melts into a psychedelic union with them. When they finally emerge after sundown, Elliot watches the vast crowd and brilliant lights of the distant concert ripple with harmonious hallucinatory visuals that swell into serene white light.
Elliot returns home from his liberating experience and has breakfast with his parents. He suggests to his mother that they now have enough money to replace him, but she cannot bear to let him have his freedom. Elliot storms out, facetiously suggesting his mom eat the hash brownies Vilma has just offered. After another beautiful day at the festival, during which his friend the Vietnam veteran, Billy (Emile Hirsch), appears to overcome his Post Traumatic Stress Disorder, Elliot returns home to find his parents laughing and cavorting hysterically, having eaten Vilma’s hash brownies. The once-brittle family (particularly Sonia) are united in joy and delirious affection.
The next morning, however, Sonia inadvertently reveals that she has secretly saved $97,000 in cash in the floorboards of her closet. Elliot is upset that his mother hid this from him while he put his own savings into helping his parents.
After the final day of the concert, Elliot packs up his life and says farewell to his father, after his father encourages him to strike out on his own. As Elliot pays one last visit to the concert and looks out over the muddy desolation of the Yasgur farm, Lang rides up on horseback and they marvel at how despite the obstacles, the event was a success. Lang mentions his next big project: staging a truly free concert in San Francisco with the Rolling Stones – the infamous Altamont Free Concert.