One thing I appreciated more on re-watch was the commentary on how much the media we consume can dominate our memories and thoughts. Lucy drops the the Oscar Wilde quote about "most people are other people. Their thoughts are someone else's opinions, their live a mimicry, their passions a quotation". The old guy's mind is stuck on 'trivial pursuits' and almost everything running around his head is a media reference.
i think another aspect of this is that for the janitor, it's also the only thing he has to fall back on i.e. he has no life memories of his own. it's just a lifetime of regrets over the inaction in his own life so he has to live vicariously through the media.