It's not a film, but a very significant example of being trapped on VHS is CNN's Cold War documentary. 24 hour-long episodes covering the whole Cold War, start to finish, with an unbelievable roster of interviews including Fidel Castro, Walter Cronkite, Henry Kissinger, Robert MacNamara, Gerald Ford, Jimmy Carter, Jeane Kirkpatrick, Lech Walesa, Aldritch Ames, Mikhail Gorbachev, and more.
Never released to DVD, because the series came out in 1998. Then 9/11 hit, and material in episodes 19 and 20 that covered the Russian Afghan war were re-classified by the Bush administration; CNN would not be allowed to republish that material. The DVD market went big-time shortly after, and CNN decided not to transfer an incomplete product.
If you ever get a chance to see it, do so. It's worth your time. It's a pity that you pretty much can't obtain it legally anymore.