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Romance and trains. They're intimately linked. Ask Alfred Hitchcock. He has great fun doing the 39 Steps in the best adaptation of the story there's been. Brief Encounter is far more chaste, but the feelings smoulder away igniting ever seen that Celia Johnson and Trevor Howard share. Brief Encounter wins.
I love the romance and adventure of train travel in a bygone age which both these films conjure up - and I can't decide! Oh okay then, 39 Steps...
I don't really get the appeal of hearing some bored housewife's tale of woe, so Brief Encounter wasn't an enjoyable movie for me. The 39 Steps, though, is always a good time. Mr. Memory for the easy win.