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Tear Jerker: Withnail and I
Monty's farewell letter to "his boys" is incredibly sad.
The sight of a despairing Withnail trudging away in the rain is haunting.
The scene in the cottage where Monty attempts to force himself on Marwood. Despite the fact that Monty has just tried to commit rape, the moment where his face moves into the light, and we see that this desperately lonely man has put on makeup to try and make himself more appealing to the much younger and more conventionally attractive Marwood is one of the saddest moments in an incredibly sad film.
While not in the film itself, the published script has one in its foreword. In it Bruce Robinson recounts tales of himself and Vivian (the man Withnail is based on) back in the 60s. It's all fun and games until the final paragraph, where it drops the line "And I can't believe Vivian is dead. He got cancer of the throat and they tore his voice out." The rest is absolutely heartbreaking.
Marwood's fare-well: "I shall miss you, Withnail."
The fact that only a pack of wolves know just how good an actor Withnail can be. Especially that in the original ending Withnail kills himself with a shotgun.