1) Apocalypse Now
The Production:
This one is the granddaddy of shambolic productions. Francis Ford Coppola’s Apocalypse Now took almost a year to shoot, Filipino storms wrecked the sets, and the film became so bloated that the budget swelled from $14 million to over $30 million.
Original star Harvey Keitel was fired, his replacement Martin Sheen had an alcohol-fueled breakdown (as seen in the film) and almost died of a heart attack, some of the cast were on drugs for real, and Marlon Brando turned up to the set overweight, having not learnt his lines. Also, Coppola considered suicide as an escape, almost understandably.
The Film:
Apocalypse Now began shooting in 1976 (prep had been going on since 1975), and didn’t see release until 1979. Most of the time, this would be a warning sign, indicating that the film in question wasn’t any good. But Coppola – perfectionist that he was – had just been holed up in editing since the film’s wrap in 1977. The final product revealed itself to be a phantasmagorical war-is-hell masterpiece, created by someone treading a very fine line between madness and genius.