Huh... been a long time since I properly bought a game that wasn't a present for someone. In reverse order, I think...
Gran Turismo 3. They really should have held it back and finished up the rough edges (terrible car handling, road surface lighting that was all over the place, etc). GT4 was, basically, GT3 with the splinters sanded off.
A mini plug-in-the-tv Megadrive with Sensi Soccer, Cannon Fodder and Mega Lo Mania built in. I love them all like children, but the latter two just aren't playable without a mouse. Or if you really have to, a joystick. D-pad is a very poor cousin. Should've spent the money on restoring (or ... shock! ... replacing) my old ST. Brother's matching one with Street Fighter and Ghouls 'n' Goblins was a much better choice.
Some other PC racing thing called Legends of Gran Prix or whatever. Couldn't get it to run without crashing. Shame, it looked really interesting until then. Got a refund at least.
Taz-Mania on the gamegear

shockingly bad excuse for a platformer, despite having some unique play-style ideas.
(and Klax, which is a terrible puzzler... but that was at least secondhand, along with Transbot on the Mastersystem)
And some horrendous "rally" driving game on the Speccy where everything was in stark black & white, and the cars only moved in the four cardinal directions. Must've been a 16k title. But to think of all the true classics that could have been had with the same money, to be played in the limited time (summer holidays!) it was borrowed from the school where my mum worked... I mean hell, we could have had Ant Attack for a couple of quid and THAT was also 16k.
All about the emulators and hand-me-downs these days (which I pay for in xmas presents), so I ain't bovvered.
(and now, some unexpected star purchases: A tetris-based multigame at a spanish market for about 1000 pesetas (£3?) which in the end our family had to buy a second of to stop fights over it. Screen resolution of like 10 by 20 pre-patterned pixels, but with about 8 different games, all as addictive* as crack. Knockoff multi-cartridges for our single B&W GB Pocket, even though all we really played of them was Tetris, Mario and Bombjack. Defenders of Oasis for GG, and the classic 4-in-one cart. And to no-one's surprise, FF7 for PC, which my bro is still keeping in pristine condition - far better than the PSX one, and worth the effort we had to put in to get it working. Oh and Z:LA for that same GBP of course.)
* Dear world. THIS is how it's spelt. It's not hard.