Here's my answer to question 1 from the below inquiry:
As long as it takes you to subscribe to Vice magazine, move to Williamsburg, ravage a thrift store for ironic T-shirts and creepers. That's precisely how long it takes to become a hipster, which is of course why hipsters are all so full of shit. And as for 'proving yourself,' it seems to depend completely on which hipster species you are being sunk into, but generally a few prompt name-drops will do. Here are a few names (in no particular order) that can be dropped in almost any hipster situation — from crooked trucker cap to tweedy academic — and are sure to evoke the universal gurgling hipster 'coo,': Bob Pollard or 'GBV', Yo La Tengo, James Joyce, Stanley Kubrick, Charlie Parker, Crumb, Christopher Hitchens, Brian Wilson, 'Indy,' Illuminati, Don't Look Back, Cocksucker Blues, Eat The Document, Samuel Beckett, Betty Page, Derrida, Foucault, Kindercore, 'Alt-Country' … but really it's much, much simpler than this because such is the nature of the hipsters that they will believe almost anything in order to avoid looking 'out of it.' As they get older of course they sometimes wise up, but the young trucker-cap Williamsburg loft-dwellers are a cinch, all you have to do is condescend to them a little and drop some esoteric references and you're sure to become a hipster in no time at all, and that's the truth Jack.
On the topic of a hipster initiation ceremony: The real clincher for you to be initiated into the hipster clan of your choice is a matter of mutual distaste. Yes, I did say distaste. See, in the end hipsters are really just connoisseurs of shit, hence all the nostalgic knick-knack-of-the-past worship (and believe me, the Dukes of Hazzard and Gremlins were never that cool), all you really need to do to be accepted is find some pop culture objects or icons from the past that you know in your heart are completely fucking ridiculous and then pretend that you think they're really cool. To give an example of some cultural trash that is sure to end up on the hipster barometer in the future: American Idol, Survivor, Oprah's Book Club, Anna Nicole Smith, Razor Scooters, Martha Stewart, NASCAR, Justin Timberlake, Destiny's Child, Hot Pockets, and all the boy bands. And you better believe that with so much pop-culture garbage being produced in the 90s, with the poop factories in overdrive for the better part of ten years, we are set to produce some fucking hipsters like you cannot imagine, hipsters that will shock even the palest, poutiest, indyest hipsters in the biggest co-op lofts in all of Brooklyn. Yes my friends, we are in store for some fucking beefed up frankenhipsters in the next decade, I tell you. As soon as all that culture garbage shuffles off into the collective brain and gets a little bit dusty, when it starts popping up in garage sales in Ohio and Wisconsin, that's when the hipsters digest it, they live off shit, plain and simple. And like the butterfly whose colors reflect its flower of choice, so will the frankenhipster come back to haunt us with second comings of all the worst and most absurd elements of our society. But I'll get into future hipster projections another time.