He's the embodiment of 90's slacker culture. Something only a boomer could truly achieve without trying.
Earlier in his life he was with 'it' and trying to change things but then he just gave up trying.
He also represents the essence of the appearance of being hip without trying that underpinned the boho hipster cultural ideal of the 2000's. At which point actually being that thing was not possible due to the high prices of rent.
The irony is that the price of authentically being that meant he was irrelevent in his own time when he actually achieved that ideal as he has virtually no clout.
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