There have been some pretty memorable ones for me...
First, I love baker, the team, all that shit, but no matter how many I've had, I just don't like them, only had the blitz ones though.
Definitely any alien deck I've ever had, weirdest, most uncomfortable shapes.
About a year ago I tried out a real for the first time, it was the 8.06 shape, easily one of the worst boards I've had.
Indy lows, actually any low truck I've ever had.
And most recently trucks, bought those new thunder titanium light, 147 hi's, and I just can't get used to them, the stock bushings are weird, and when I put bones mediums in them, they turn all tight, which I don't get at all, because they turn a little too loose on indy's, idk I think it's cause I've been riding indy's for as long as I can remember.