I've been doing this basically since I started playing video games, and despite my music tastes shifting wildly between then and now, I occasionally bust out the embarrassing stuff when it's the right time (aka moments when I really feel the urge to play some Need for Speed game and therefore need to dust off my ancient dir en grey playlist that literally only still exists for this reason). Pretty sure a lot of it stems from when my old roommate's boyfriend and I binged out on the snowboarding minigame in FFVII for literal days and realized that Cake's Fashion Nugget album seemed to give it a new life. Yes, both of those things were still entirely relevant at the time. My friends and I spent a lot of time and effort trying to match up music to FF cutscenes too; FFX was our favorite because there was a whole goddamn theater you could replay the scenes at, at your leisure and that was A+ in our books. (Leonard Nimoy's Bilbo Baggins song, set to Auron showing up and looking badass in Luca, never 4get etc)
Sometimes it's super specific; the Junkie XL remix of that Elvis song is fucking hilarious when you're playing Xiaoyu in Tekken Force mode in Tekken 4. These days, because I'm old and tired and a lot less motivated, it's generally whatever I'm listening to at the time getting attached to the game itself where when I go back to the game later I have to put the music on. F+TM's Ceremonials got attached to Diablo 3. Glitch ended up tied to My Brightest Diamond's All Things Will Unwind when that was around. VNV Nation/Apop and other 90's/00's EBM in that vein for the Mass Effect series. The most effort I put into it is the playlists I used to build for my specific favorite commanders in Guild Wars 2.
If you do like doing stuff like this though, you might check out Audiosurf. Inexpensive, soothing mindrelease of a game where you choose your own soundtrack and it builds courses for you based on what you've chosen.
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Sometimes it's super specific; the Junkie XL remix of that Elvis song is fucking hilarious when you're playing Xiaoyu in Tekken Force mode in Tekken 4. These days, because I'm old and tired and a lot less motivated, it's generally whatever I'm listening to at the time getting attached to the game itself where when I go back to the game later I have to put the music on. F+TM's Ceremonials got attached to Diablo 3. Glitch ended up tied to My Brightest Diamond's All Things Will Unwind when that was around. VNV Nation/Apop and other 90's/00's EBM in that vein for the Mass Effect series. The most effort I put into it is the playlists I used to build for my specific favorite commanders in Guild Wars 2.
If you do like doing stuff like this though, you might check out Audiosurf. Inexpensive, soothing mindrelease of a game where you choose your own soundtrack and it builds courses for you based on what you've chosen.