Possibly the best sonic investment I've ever made is my 20 year old set of Sony MDR-Cd770 Digital Reference Headphones.
I've listened to countless other headphones since and often thought of an update, only problem is that nothing sounds as good as these !
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The absolute best set of earphones I’ve ever had, and in fact still own after some odd 20 years, is a set of Sony MDR-CD770 Digital Reference earphones. They (still) sound amazing, you feel like you can point out the location of every instrument in the band you’re listening too, like they were in the room.
The only problem with these are that they are big, expensive, and fragile. You won’t be taking these with you when you’re on vacation. They wouldn’t survive the suitcase, and they’re impossible when you are trying to lay your head down to sleep while listening to good music. Even if you did, you’d never wake up again, being strangled by the many meters of audio cable dangling off of your left ear.
But if you’re sitting at home on the couch, these will beat the * out of any soundsystem anyday, without annoying the neighbours. You’ll be amazed at how good a high-bitrate AAC track sounds comming out of your iPod.