Not usually, but today yes. I was listening to You me at six whilst playing WoW, and now I'm listening to Killswitch Engage whilst just going forum stuff. If you know neither of those bands, the names should be indications enough that they don't suit the activity
The station I listen to the most in Saints Row 2 is the classical one. Classical and opera fits so well in a freaky way when it comes to open sandbox games like GTA and SR. Car chases, death and destruction with some slow moving opera in the background... priceless.
Other than that, I had a large playlist I went through while playing Dead Rising. Wonderful World, Jakety Sax, Don't Stop Me Now by Queen etc. Dunno why, but it makes it a bit more fun.
I dont usually listen to anything else than the in-game music while playing, but when I play games like saints row 2, I always end up finding the most inappropriate music when what Im doing.
The first and second xbox has support for custom soundtracks btw.
I stuck the soundtrack to Railroad Tycoon 3 in the Hip Hop radio station folder on Sims 2. You haven't lived until you've seen a bunch of Sims gettin' they groove on to "Turkey in the Straw"...although Sims doing WooHoo while "I've Been Workin' on the Railroad" played in the background was pretty close on the Funny Scale.
Apart from that I don't really do it so much apart from just putting music on while gaming... I have a mean streak when I put 'lecher *****' on to CSS.
As I said earlier I shuffle, I found myself this evening playing HL2 with The Hitchhikers Guide to the Galaxy Radio Series came on. I had to pause it so I could stop laughing on several occasions.
GTA San Andreas + Wesley Willis. There's nothing like being chased by cops in a cross-country escape route, with good ol' Wesley shouting "Rock 'n Roll McDonalds".
Napalm Death and Devil May Cry 4 is in interesting combination. As is Gallows, Dillinger Escape Plan and anything else that's either fast or chaotic while playing Burnout Paradise (surprisingly it actually puts you more in the zone, less crashing).
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