Some that have moved on from me through the years, these are the ones that stand out as particularly troublesome:
Beretta Bobcat and Taurus PT-22: Fun at the range, but never could get them to not jam. Tried at least 5 brands of 22lr in them with no success.
Polish P-64 in 9x18 Mak: Kicked like a mule and heavy DA/SA trigger pull. Great for carry, never enjoyed my range sessions with that one. At least it was cheap at the time (2004-ish timeframe).
Walther PPK/s in 380: Bit the web of my left dominant hand every time, drew blood, left a scar for a while. Lovely looking though, and heavy for carry compared to other 380's.
Kimber micro 380: Prettiest handgun I have owned. As a new, old-stock pistol it jammed more than any other gun I have owned. Never got it to function properly. Total disappointment after hearing how great the brand is through the years.
Pawn shop .32 acp Italian pistol/Walther PPK clone. I can't remember the model or make, jammed every round. Sure wasn't a Beretta- that I remember. The pawn shop took it back.
Star BM 9 mm: Jammed every other round. It was a cheap surplus pistol, and I found out why it was cheap. It looked better than it functioned.