This film was not meant to be a fleshed-out story with all characters specifically and precisely drawn in a neatly packaged plot.
For one thing, the director started writing the story for the film based on an 'emotion' he felt after seeing a painting. He then drew from experiences from his own youth, including people he knew for some of the characters, and built his story from there.
For another, the 'flashbacks' are precisely that -- the recollections of a rather hazy-minded middle-aged man of his youth at 15 years old, 25 years earlier. You are supposed to see it through the filter of his memory. Therefore, that is what you are supposed to experience -- memories are not precise or distinct. They are blurry snapshots at best, and the older you are, the more nostalgic they become. Certainly Ruth and he did not sing together in slow motion, but that is the way he experiences that event in his memory.
The characters are not going to have any backstory because they don't need to, in Joe's mind, because he knows who they are. We are supposed to focus on what Joe is remembering and feeling.
I don't think we were supposed to know much about the how or why Joe became a successful actor (except maybe just enough as a backdrop to how his lifestyle based on hedonism and selfishness led him to examine his past mistakes, and how a rather tragic event he probably felt guilty about might have caused him to lead an empty, adult life, no matter how successful otherwise, and why he did not end up with Ruth). Neither were we supposed to 'know' something like Evelyn's motives for her behavior, just how she and Joe interacted (again, according to his memory of events) and how their interactions resulted in the outcomes for the characters it did. We might not have had any more information about his friend because the events he was remembering didn't have a lot to do with Boots.
Now, that might not be everyone's cup of tea. I found it quite a good film myself, and very moving. Made me think of spent youth and how our lives can become something quite different from what we expect when we are young. And, the music was good :)
Also, old WWII mines DID occasionally wash up on the British coastline.
"I can't stand a naked light bulb, any more than..a rude remark or a vulgar action" Blanche DuBois
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