"Holocene" by Bon Iver, yo. It's a beautiful song from start to finish but the line "...and I was not magnificent" just fucking slays me. It's devastating It speaks to being less than what was expected of you, less than what you'd hoped for yourself, and being acutely aware of the distinctly unremarkable nature of your own existence :icon-cry:
This live version of "Maybe" by Janis Joplin. The bit at 3:30 or so. The raw emotion etched on her face as she reaches for notes that her voice probably wasn't supposed to be able to reach, and the sincerity with which she laces each and every word.
Also notable about this video - the horn section: a white James Brown, a hippie and a black dood with the world's coolest afro. And the dood who does the intro: at 21 seconds he starts dancing even though there's no music playing yet and it's awesome.
There's a few different versions of "Feel Like Going Home" knocking around but this is my favourite. Charlie Rich recorded this one less than a year before he died and while it's not as desolate or as haunting as earlier versions (it's repurposed as a gospel song and takes on an almost celebratory tone) it's essentially an old dood looking back on his life with nothing but regret ("Everything I done was wrong and I feel like going home") and embracing his own death
Also, this one by Torres :icon-cry: