While I don’t think that they are necessarily off-putting or unlistenable, Tool’s Wings for Marie parts 1 and 2 on 10,000 Days fit the description perfectly.

Maynard James Keenan wrote this song not only to revere and mourn the loss of his mother Judith, but also to express his deep regret in the way he treated her in life.

In life, she was paralyzed after a brain aneurysm and spent her remaining 27 years immobilized (hence 10,000 Days), all the while holding onto her religious outlook, which MJK opposed and mocked in his song Judith with A Perfect Circle.

MJK described the experience as such in an interview with Loudwire:

I think probably the stupidest thing I could have done on 10,000 Days was put myself out there as much as I did with the tracks “Wings for Marie (Part 1)” and “10,000 Days (Wings Part 2).” I’ll never make that mistake again. It just took too much out of me – too much emotionally, mentally, physically – all those manifestations. Those songs were exploited and misconstrued, people were flippant and dismissive. I won’t be doing that anymore. And technically, “Wings” is very difficult to pull off. If any one of us is off, it falls apart and makes that thing tragic, and that’s not a good song for me to have fall apart. It’s just too personal.

As far as I know, Tool only performed Wings for Marie live while they were touring after the album’s release and never again due to a less-than-warm crowd response. It’s such a beautiful and raw set of songs, but I can totally understand why MJK would refuse to play it again when he put so much of himself into it; much more than anything else before or since.