In my opinion, 'beautifully depressing' means whatever it is used to define an act or thing, that act or thing becomes so descriptive in itself that it causes you to become lessened in energetic spirits, but not in the bad way. It'd probably be the closest way to describe 'perfection' in the utter sense of the word....
Jimi Hendrix's freestyle version of "Hear My Train A-Comin'" is mellowed down and introspective so you can see into the Man himself, beyond his gimmicks and flashy style... In rock form, the concert version can be just as mesmerizing, but this particular version I'm listening to here is 'beautifully depressing'....
by Echo Raven October 26, 2005
The Urban Dictionary Mug
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