1986. No contest. "Master of Puppets" by Metallica, "Somewhere in Time" by Iron Maiden, "Peace Sells... But Who's Buying" by Megadeth, and "Reign in Blood" by Slayer. The mind reels. These four albums are damn near perfect.
Never asking that question. That's the answer. When you and your buddies are knocking back some cold ones and listening to Pyromania on a hot summer day, do you wonder what the meaning of life is? How about when you're in the pit, or throwing up the horns while the guitarist shreds out a sweet-ass solo? Are you thinking about the meaning of life then? What about when you go to the store and you buy your favorite band's new album on cassette, the day it comes out, and you unwrap it in the car and stick it in the tape deck, and your heart's pounding, because HERE WE GO. Is it worth interrupting the glory of life to ask about its meaning? Hell no. What you want to do is turn the speakers all the way up and bang your head.
Any old-school game or retroclone should be fine, as long as you've got HP, AC, roll 20 to hit (or to save), and character classes like Fighter and Thief (even better if you've got Ranger, Druid, and Assassin in the mix, but that's not absolutely necessary, it's just cool). Modern OSR games like Silent Legions would also work well!