Jennings Bryco 380. Honestly a hunk o crap. I actually out some time into it and played with the feed lips and slicked up the front of the follower and polished the ramp. Last time I shot it (with a friend that was looking for a small 380) it only failed to fire twice out of about 100 rounds. Before that, it generally could not make it through a magazine without a failure.
For guns that are generally considered quality guns, I've had two failures ever with a KelTec P32 (I've owned three, two with no failures ever) and two failures with a Springfield Loaded (I've owned about six, five without failures) I also had a Springfield 9mm Loaded pistol that had maybe five failures ever. All from the same magazine. The other magazine and the replacement for the bad one never ever failed so I don't really attribute that to the gun. I also had a early 90s Colt 1991 that wouldn't feed any HP ammo that I tried and probably had 10-15 failures with ball ammo out of 400 rounds. I have another early 90s 1991 that has been excellent and is one of my very favotite pistols of all time.
I have a friend that has two guns, a Ruger 45 and a Hi Point 9mm. The Ruger has had maybe two or three, the Hi Point has never failed. I think it's largely the luck of the draw. I've owned several many pistols and have very very few that were lemons,