1. iPhone/A Game Boy Duct-Taped To A CVS MP3 Player
Let's get this out of the way first: I know that this travel advice series is called "Traveling With The 99%," and that in light of that concept, it's more than a little off-putting to have the first essential travel item be a $400 smartphone. Therefore, I've come up with a compromise solution: you can replicate the functionality I'm recommending an iPhone for by duct-taping a Nintendo Game Boy to a
$29.99 Craig™ brand mp3 player. Based on the eBay going rate for Game Boys, I'd say you can, with parts and labor, whip one of these bad boys up for a cool $50 even.
But I'm guessing you also know plenty of people with smartphones, including a few people who would really be better off spending their money on more essential things. And strictly within that context,
holy shit is the iPhone amazing to fly with. You can watch movies, listen to music, play some pretty sophisticated video games (and/or Scrabble and Sudoku). All of these are absolutely essential, especially if the guy next to you is trying to tell you about his cats, or if he's digging for buried treasure in his nose, or many of the other unpleasant possible experiences that being randomly seated can provide.
[photo via and via]