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I think the whole theme is an examination of how, even knowing that he looks at Boomers who say the same shit about the 50s/60s/70s as morons, and at Retvrners who say the same shit about the 15th/17th/18th as schizophrenics, he still can't help feeling that way about the 90s. The denouement fantasy 90s, of going to all the cool places and doing all the cool things with all the cool people, is the capper; that's how we always idealize a time period. People rarely feel nostalgia through a Rawlsian Veil of Ignorance; maybe Gibbon. We rarely think "On average, people in time period X had it best." Or "I would be most likely to wind up ok in time period x."

We either think, "it would have been cool to live in the 60s and go to Woodstock and hang out in the Haight and do drugs and have love ins with pretty girls." Or we think "If I as an individual, with my unique skills and tastes, were transported back to the 50s intact, I would crush it."

We never think "What if I go back to the 60s, but I'm an ugly guy born in a trailer park working a dead end job in a cardboard box factory, I never get a good education or hear much about the world because my religious parents keep me from most media, I only vaguely hear about Woodstock and the Haight after the fact."

When we time travel, we always imagine ourselves in the thick of the action. Which most people weren't. Freddy's "Friends" piece that's being argued about further down is kinda asking the question: should media present an aspirational normative view of cool people as cool people should be? Or should it present the average person who has only a vague interest in politics and events?