This is a great thread.

As for Bruce, his first seven or eight albums have a firm place heart that speaks to by blue collar upbringing and my journey into adulthood, but I understand why people don't connect with him.

Same with the Grateful Dead.  It took me quite a while to get around to them and dive in, but American Beauty and Workingman's Dead were the gateway, followed closely by the Barton Hall '77 bootleg and the live albums that followed American Beauty (Grateful Dead and Europe '72).  I still don't get their second and third albums, though, the ones they supposedly mixed while high on acid.

Dylan is another one of those who took me a while to connect with, and I will say that most of my friends don't understand him, either.

One album that's supposed to be great that I've tried (and failed) to appreciate is Radiohead's OK Computer.

At the top of the "I don't get this" heap would have to be Captain Beefheart's Trout Mask Replica.  Safe as Milk is pretty darn good, but this follow-up is too much like that annoying guy in high school who is genuinely trying to be annoying (and succeeding).  There are many artists and critics I respect who revere this album, but I've tried and been left baffled.  I've been told you have to take it in pieces and let it grow on you, but anything that takes that much work to enjoy can be left by the side of the road for something my heart naturally connects with.

There’s no accounting for taste. One man’s wall hanging is the next they’s door mat.

Rammstein and Hüsker Dü aren’t my cup of barf where as others don’t get the seminal “Kind of Blue”

I will never ever ever ever understand Rush. I don't know what annoys me more, them or black metal.  what is the point of barfing into a microphone and recording it?

Miles Davis and "progressive jazz" in general after Kind of Blue/Sketches of Spain.

Too much rock, blues, classical, folk/acoustic, big band - "proven" and new - to enjoy for me to use too much time trying to "get" music that doesn't resonate.  My candle of time is way shorter than it was when I actively sought new music appreciation experiences. YMMV

I agree on Graceland. Good, but far from mind blowing and hardly worthy of the massive praise it received. If you jump around to different tracks you can hear Simon using identical phrasing on many of them. Gets a bit repetitious.

One genre that I never cared for was the new wave whiny British sound of bands like The Cure, The Smiths, Depeche Mode, New Order, Flock of Seagulls, etc. that can best be represented by the album Republic by New Order. Like many of the albums from those bands, there might be a good song or two, like Regret on Republic, but then the rest of the albums are pretty much garbage. Having grown up on The Beatles, Led Zeppelin, The Who, The Rolling Stones, Queen, etc. that whiny new wave sound never did it for me. But there are a few songs from those bands that I do like, such as Ghost in You and Pretty in Pink by The Psychedelic Furs, Space Age Love Song by Flock, and all of Tears for Fears, which manages to be new wave but not whiny.