Taking Woodstock

A 2009 film by Ang Lee, Taking Woodstock tells the story behind the creation of the titular music festival. In 1969, young Elliot Tiber returns to his parent's motel in the Catskills after a failed attempt at a career in art and design in New York City. His parents are in danger of losing their business and their home, so Elliot--the president of the local Chamber of Commerce--feels it's his duty to keep that from happening. Every year he gets a permit to host a local music festival, and 1969 is no different.

Well...there is one difference. See, in the summer of '69, one of the neighboring towns pulls its permits for a potential concert with the Woodstock Group. Elliot gets it into his head, seeing as how he already has the permit, to move the festival to his parent's motel in White Lake. Needless to say, Hilarity Ensues.

Tropes used in Taking Woodstock include:

Calling The Old Woman Out: After going through the entire film belittled and mistreated by his mother, Elliot reaches his breaking point. After finding out his mother had saved up 97 thousand dollars over the course of her life, but nevertheless expected her son to bail her out of all her financial woes, Elliot has it. He calls her out, then leaves.
Everybody Must Get Stoned: Some of the funniest moments in the film come when straight-laced Elliot stops giving things a pass
- Not to mention his parents...
Financial Abuse: Elliot has always supported his parents, putting all his own earnings and savings into their failing motel. Only to find out his mother's been hoarding money all her life, and could have bailed herself out if she hadn't made Elliot do it for her.
Historical In-Joke: Darkly done. At the very end, Michael tells Elliot that he's planning a truly free concert... in Altamont.
Jerkass: Elliot's mother, which isn't surprising since her actress, Imelda Staunton, is known for playing complete Jerkass characters.
Naked People Are Funny: The Earth Light theatre troupe
The Sixties
The Stoner: Several, though Michael especially
Invisible to Gaydar: Elliot
The Vietnam War: Referenced many times, especially regarding side character Billy, who's a veteran suffering from flashbacks
Wholesome Crossdresser: Vilma