Neither film is particularly insightful. Both revel in cliche and heavy-handed delivery of messages. Taking Woodstock tries to tell people to believe in themselves, and break loose by having Elliot (Dmitri Martin) discover his homosexuality and get high on acid to Jefferson Airplane's "Red Telephone." Long sequences of haziness illuminate the freedom of drugs. Similarly, Pirate Radio tries to sell people on the idea of fighting for what you believe in by having Radio Rock's entire crew agree one by one to stay on the ship even after the government shuts it down. Elgar's Nimrod swells in the background. Long montages of random Brits enjoying Radio Rock illustrate music's liberating effect. We get it: music equals love, democracy, and all that is good in the world.
The one thing that makes Pirate Radio more entertaining to watch than Taking Woodstock is that Pirate Radio takes itself way less seriously. Maybe it's the British sense of humor, but the film seems to wink at us during a ship-sinking scene that reminds one of the drama of Titanic. Things are resolved a bit too easily, but also with humor. In one set piece, two DJ's play a game of chicken by climbing on to the mast and then jumping off. Plus, the music selection is fabulous. Pirate Radio hits all the Sixties greats aside from the Beatles, including Cat Stevens, the Beach Boys, and Leonard Cohen. Taking Woodstock only has some snippets of Woodstock acts. Though Pirate Radio is a bit long clocking in at 2 hours, its soundtrack makes an otherwise vapid movie bearable. Too bad Woodstock can't say the same.