first off, I'm gonna say that this isn't just about bad music recommendations-- it's also about music recommendations that are terrible considering the source and the destination. I've had people suggest bands to me that I acknowledged, in the abstract, where not that bad-- but I still didn't like them. like Pearl Jam, Nirvanna and Radiohead. they didn't suck, they just didn't grab me. no, I'm talking about "wait, seriously, how did you even come up with that? you've known me for how long... and you came up with this?" recommendations.
so one day a family member was asking me what I was listening to-- and I said "the Dixie Hummingbirds". "really, who are they? I've never heard of them." I said, "they're like one of the grand-daddies of gospel and soul. they're pretty awesome." to which said family member asked, "why have I never heard of them?" I replied, "well, if you've heard that Paul Simon song 'She Loves Me Like a Rock' then you've heard them in action.' a brief pause, 'oh! well if you like them you'll LOVE the Bill Gaither Band!'"
cue test listening....
it was actually worse than "if you like Ray Charles you'll -LOVE- Michael Bolton". and I didn't think that was gonna happen! I think I understand where this person was coming from... they figured that if I like liked old gospel and R&B that I would like the badly-watered down white-bread copy from 40 years later.
any painfully bad music recommendations that were funny for you?
"If you like <insert name here> then you'll LOVE <insert name here>"