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Beeper Salesmen: Robert Pataki — Hey Arnold!
The beeper kings of the world have lost their crowns. Not even wannabe mogul Dennis Duffy could make a go of the business in a post-iPhone world. Surely, Helga's resourceful dad would have landed on his feet, becoming the sultan of selfie-sticks.
Film Boxer & Shipper: Daniel Hillard — Mrs. Doubtfire
While I'm sure there's still someone tasked with physically moving canisters of films between studios, it seems more likely that in today's world, transferring movies would involve different directions: You compress the movie file, then you e-mail it.
Video Rental Clerk: Randal Graves — Clerks
Netflix has given us so many wonderful adventures in binge-watching, but it also helped speed up the demise of video stores. And with them, the dream job of every aspiring screenwriter, director, and critic under 22 went the way of the dodo. Today, Randal would only look disinterestedly at Netflix ratings, not VHS boxes.
Cyber Cafe Worker: Animorphs
Though they're still popular abroad, cyber cafes are not where the cool animorphs would check AIM away messages today. Now, we just depend on Starbucks and its free WiFi for that. Which is a shame for would-be teen baristas, since listing cyber cafe on your résumé makes it seem like you spent your afternoons with Zenon.
CD Seller: Warren from Empire Records
If you really want to sell vinyl, you still can, whether at a small used shop or at your local Urban Outfitters. But it's not likely you'll ever work at giant musical mecca like Empire Records — and you certainly won't be shilling CDs. (We'll have to wait for early 2000s nostalgia for your Discman to make a comback.)