Maybe an old thread, but interesting idea. I think this movie worked magnificently BECAUSE of the 60s film-making qualities it had. The narration and odd style wouldn't translate as a modern film, so you'd need a director with a different kind of edge who could somehow still bring the same quirkiness, but in a fresh (un-pretentious) way.
Not sure about casting. Definitely think you're right about Jemaine, but I absolutely adore him. only actor I can immediately see myself being charmed by, given the fact that he's a live-in lover.
Rachel McAdams is also another nice choice. She's got just enough beauty and depth for it, without being too innocent.
If he was just a little younger, I could see William H. Macey playing Mr. Blossom. Given that he is, alas, maybe a decade too old now, perhaps Ewan Mcgregor or Edward Norton?
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