The movie opens with a British customer asking Sonia Teichberg (Imelda Staunton) for $7 back as a refund for his motel room, which he says is less than satisfactory. The room is dirty, the air-conditioner is just a plastic box propping open the window, and there are no towels. Sonia points him toward signs behind her counter that read there is a no-refund policy and towels are an extra dollar each. They begin to argue and are interrupted by Jake Teichberg (Henry Goodman), her husband, and Elliot Teichberg (Demetri Martin), her son and the main character of the movie.
Elliot is an aspiring interior designer who has moved back home to help his parents with their upstate New York motel, which is not doing well in all ways possible. He is a soft-spoken and as we find out later is “in the closet”. Jake is a tired but kindly man, and it is hinted throughout the movie that he has several ailments. Sonia may very well be the source material for every negative stereotype attributed to a Jewish mother.
Jake and Elliot tell Sonia they need to get to the bank for a meeting, leaving the frustrated customer behind as she tells them he was threatening her. During the meeting with the bank rep, we learn that Elliot is the youngest president ever of the local Chamber of Commerce. This doesn’t carry much weight apparently as the result of their bank meeting is that they have until summer to pay their loans or the motel will be foreclosed. Sonia heads back home, distraught. Jake tells Elliot he can’t wait until they take “the dump” away and he’d burn the place down himself if they had insurance.
The next scene has Elliot going into New York City to pick up the last of his stuff from his place. His sister is waiting for him at his apartment there. He offers her some paintings, but she tells him she already has too many of them. She doesn’t understand why he’d go back to their parents’ place and tells Elliot they didn’t have half as much trouble letting her go. He half-jokes it’s because they love him more.
We get some scenes of Elliot’s life in the small town. He presides over a Chamber of Commerce meeting, which mostly consists of him and old ladies, a husband or two, and Dan (Jeffrey Dean Morgan), a local man who needs something approved. Dan ends up having to second his own motion. Elliot motions and approves the annual music festival he runs, which no one seems particularly excited for. Outside the meeting, we learn that Dan’s brother Billy (Emile Hirsch) has just returned from the war and is suffering from PTSD and probably other mental problems.
Elliot also spends a good amount of time debating with his parents on how to run the motel. His father pours bleach into the pool to clean it and his mother believes that as long as no one’s had sex in them, the sheets don’t need to be replaced between customers. The only tenants of the place are The Earth Light Players, a very... ahead-of-their-time local theater troupe who are often in various states of undress. They have a deal with the Teichbergs to pay their debt when their play opens. They live and rehearse in the barn.
At one point Elliot’s friend Steven calls to ask if he wants to move with him and some other friends to San Francisco. Elliot is visibly excited but ignores the offer. It is clear he wants to go but doesn’t want to leave his parents in their current situation.
Elliot is a regular at the town market/diner where we meet Max Yasgur (Eugene Levy), who is also Jewish and runs a nearby cow farm. Elliot learns here from another local that a nearby town has cancelled their music festival. Elliot jumps at the opportunity to call the organizers and see if he can bring the festival, and thus business and income, to their town.
A few days later we see a panicked Sonia who thinks Elliot has lost his mind because he’s laying clean white sheets out in an X pattern on their lawn. Before he can fully explain, we see a helicopter landing carrying Mike Lang (Jonathan Groff), his assistant Tricia (Mamie Gummer), her dog, and a few other people. The Earth Light Players have all streaked out to welcome their arrival. Mike seems grateful but un-phased. He immediately starts talking to Elliot, apparently recognizing him from childhood, while cars carrying other concert organizers pull up.
The organizers seem very pleased with the motel and decide to use it as long as they can stay there, put up offices, as long as there is adequate space for the concert. Elliot leads them out back, and everything goes smoothly until one organizer falls into a sinkhole and they realize most of the Teichberg property is a swamp/lake area. Elliot tries to convince them to pave it, nuke it, whatever it takes to make it work. Mike seems amused by his eagerness and creative thinking but declines. The deal seems off and everyone start to leave. Sonia runs out of the house carrying glasses and cartons of New York’s finest chocolate milk, produced right up the road at Yasgur’s farm. This gives Elliot an idea…
The next scene takes place at Max Yasgur’s farm, where Max and Mike are talking business. They settle on $5,000 for the rent of the place as long as the concertgoers clean up after themselves. Max seems very agreeable; he even offers them space for parking and promises to take care of the neighbors, who will surely complain. As Mike and company leave, he hands Elliot a brown paper bag filled with cash, a down payment on the summer rental of the entire Teichberg motel and property.
Elliot brings the money home and shows it to his parents. Everyone is very excited but they are interrupted by a call telling Elliot he needs to head back to the Yasgur farm because something is wrong. Sonia grabs some of the money and tries to run off with it.
Back at Max’s farm, Elliot nervously watches a meeting between Max and the organizers. Max has found out that the organizers should be paying something more along the lines of $75,000. Both parties are trying to play hardball as Land notes, they have started a second round of chocolate milk. Lang tells Elliot not to worry. Elliot goes outside talks to Tricia and asks if Lang is “for real” because he’s always so laidback about everything. Tricia responds that Lang, like the organizers, are always laidback as long as they know the money coming. She confidentially discloses to Elliot that over a hundred thousand tickets have been sold, so no one is worried... and he shouldn’t be either. Off-screen, the organizers and Max eventually settle over an undisclosed amount of money.
The rest of the movie focuses mostly on the set-up for Woodstock, which takes place very quickly and often involves the use of split screen. (Original Woodstock Movie type of split screen.)
One night while working with his dad at the motel’s bar, which gets busier and busier as the festival draws near, Elliot meets a man named Doug. Doug is working construction, for the offices at the motel, and at the venue. He shows off his handiness by fixing the bar record player. Elliot seems embarrassed that the first record Doug plays is his Judy Garland live record, but they talk about Elliot meeting her. He says she was full of life. He kind of hits on the Doug, but Doug politely excuses himself, saying he has to go meet up with a redhead.
The organizers erect offices and start installing phone lines while the Teichbergs begin selling tickets, as they are the official box office for the festival. Many hippies arrive. One of the first is an interracial couple who are speaking entirely in slang, so Elliot needs to translate for his parents. They also start changing things at the motel. Elliot at one point walks into room 12, the door of which has been Sharpied with “12a, 12b, and 12c” Mom and dad putting up curtains in rooms to divide them into more rooms. They say the hippies don’t mind.
Eventually some mafia thugs show up and try to extort the Teichbergs for money for “protection.” Elliot’s parents end up attacking them, his father with a baseball bat and his mother with her brute strength and anger. They chase the thugs off the property, which all the hippies in line for tickets applaud.
Soon after Vilma (Liev Schreiber) shows up to offer protection. She (?) is a transvestite, as well as a former marine. Vilma used to date the sugar daddy of Elliot’s friend Steven, which is how she heard about the festival. She’s acquainted with the mafia thugs from other towns and brandishes her gun, offers her own services as a form of protection. Elliot accepts. She clearly has inferred that Elliot is homosexual also but never brings it up. She ends up getting along with Elliot’s father surprisingly well.
The motel fills up with customers, all awaiting Woodstock. The local townspeople grow angry at Elliot because they worry the hippies will trash the town once the concert comes. Some put up signs across from the motel advertising their own room and board. Local kids spray paint anti-Semitic and anti-homosexual slurs on the side of one of the buildings. Elliot and his dad agree it wouldn’t be worth it to call the police since everyone in town seems against them but they do repaint the wall before Sonia can see it.
The only local who seems truly supportive is Billy, who Elliot has been trying to welcome back home. Elliot even tries to take part in one of Billy’s flashback when he finds him crawling in the woods, which Billy shrugs off. After Elliot is refused service at the market/diner Billy tells Elliot not to let the “motherfucking motherfuckers” stop him. He also admits that he misses Vietnam because over there he was normal. He suggests going on another war tour would be better than staying in town.
As the motel fills up, the pool becomes off-limits for swimming and bathing, as people have started using it as the source for drinking water.
Back at Max’s, the preparations are underway. People have put up stages and tents. Mike Lang has taken to riding on horseback because he says it’s the fastest way from the farm to the motel. Max tells Elliot not to worry about other the townspeople because even the ones who refuse to admit it, are making money off the festival. He shakes his head telling Elliot that he saw someone charging a kid a dollar to fill a bottle with water.
Another night at the bar, which is busier than ever, Vilma and Elliot share a laugh over the fact that Elliot has started having identical complaints to his dad (no sleep for three days, the beer is warm, his hip is hurting). His dad takes a break, sits down, and starts chatting with people. Vilma tells Elliot that Jake gave her a great tour of the place, including his favorite place down by the lake. Elliot retorts that his dad has no favorites and hates the place. Vilma isn’t so sure. They do shots and Elliot ends up on the dance floor. A girl starts kissing him, and he looks very uncomfortable. Doug the carpenter sneaks up behind him to kiss him. Elliot pulls away a second then grabs Doug and kisses him passionately. After he turns toward the table where his dad is sitting to see if he saw, but Jake is gone.
Elliot does a press conference after smoking up with Tricia to calm his nerves. He skirts the issue of whether he has legal authority to put on the festival. People have complained and several agencies are on his case, mostly about the unlivable condition of the motel but Mike has lawyers and brown paper bags (money) to fix those problems. While high, he gives a speech about being free and freedom which is widely interpreted as the concert being free... unsurprisingly drawing more crowds.
In an attempt to win the town over, Elliot organizes a free pre-show a day or so before the concert. The audience is comprised of hippies and curious families from the town. Guitarists and musicians play. The Earth Light Players put on a scene from their upcoming show, which ends up with them, yelling at the audience and taking all their clothes off. The parents quickly take the small children away. Billy gets naked too, much to his brother’s Dan’s annoyance.
The day of the concert, Elliot walks down to the swamp/lake area and sees that people have started bathing there. Everyone can hear the music starting from Woodstock. Jake and Vilma are also there and Jake tells Elliot that maybe he should go. Elliot hugs his dad, almost hugs Vilma, and then runs off.
At the road in front of the house, Elliot encounters a cop who informs him that all the roads leading to the concert are basically a parking lot and the local government has issued some state of emergency. The cop came out to hit hippies, but he admits to being affected by all the energy and probably the fumes from all of the weed. When Elliot tells him it’s all his fault, the cop offers to take him for a ride on his motorcycle since it would take him hours to get to the venue on foot. On the way, Elliot sees people selling food and drink, flashing peace signs and anti-war signs, nuns, burning bras, some giving food away for free.
When he gets to the concert, Elliot ends up getting high and dropping acid with hippie couple in a van. He comes out later wearing a hippie shirt and watches the sea of lights and people with the chick. The movie never actually shows any of the Woodstock performers and Elliot never actually makes it anywhere within view of the stage.
He returns home in the early morning. The parents ask him if he’s hungry, so over breakfast they end up in an argument over Elliot’s future. Jake seems indifferent but Sonia of course wants him to stay. Elliot says they’re rich now, so they should just hire a permanent staff for the motel and take it easy.
Vilma and friends, who have baked “special brownies”, interrupt the argument. Elliot declines, and after Vilma leaves, his mother yells at him for not offering her any. He starts yelling at them, particularly her, telling her that he is the only one in town right now getting yelled at by his parents. Janis Joplin and Jimi Hendrix’s mothers surely aren’t backstage nitpicking on them. He leaves, telling both his parents they should have a brownie, or better yet two.
He returns to Woodstock, this time running into Billy who has very vivid, clear memories about a hill they climb. Billy remembers homecoming and the girl he took with him. He starts to shout that he loves this hill. The end up sliding in the mud with some hippies.
When Elliot returns home that night, he chats with Vilma who seems to be waiting up for him like a parent. Elliot asks Vilma if people know what she is. She replies that because she knows, it’s easier for everyone else too. Elliot takes the thought in and then asks what his parents have been up to since he left. Vilma says they asked for brownies after he left, like he said. Elliot is shocked especially when he finds out they had four each. He finds them dancing in their back yard. They proclaim their love for him. He puts them to bed and tucks them in.
The next morning Elliot is shown waking up next to Doug. He goes to his parents’ room to check on them where he finds his dad standing over his mom. He is worried until he sees that she is lying in the closet sleeping on a pile of cash. When she wakes up, she tells them it’s a sum over $90,000. He asks where she got it because all the concert money went directly to the bank. Sonia says it’s hers and it’s her savings. Jake is just completely surprised. Elliot is fuming mad that she let him pour all his savings into the motel and she would have let the bank foreclose when she had all this money at her disposal. He storms out.
He goes back to the concert. Everything is electrified because of the rain and faulty wiring. He chats with Tricia for a while, who tells him no one is playing because they don’t want to be electrocuted, so he heads home.
The next morning, Jake walks in on Elliot packing. Elliot swears he was going to say goodbye before he left. Jake sits his son down and tells him that a month ago he was a dying man, and although he may die tomorrow, he is “alive.” He asks Elliot if he understands what that means, and Elliot tells him no. Jake says nothing would make him happier than for his son to live and feel that way. Elliot swears he’ll come back and visit but Jake seems skeptical. As Jake leaves, Elliot asks him how he’s been able to stay with Sonia for so many years. Jake shrugs and replies simply “Because I love her.”
Elliot goes to the Yasgur farm one more time. Mike is there, still on horseback, and they watch people cleaning up the fields. Mike tells Elliot they should meet up in San Francisco, where Mike is organizing another concert. The Rolling Stones. Elliot seems interested but admits he doesn’t know where he’s going. But all his stuff is in his car, “which is a good sign.”
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