Last few years: Metro 2033, GTA4, Crysis, Arma2*
Mid noughties: Halo (looked mediocre but still ran slow), FS X*, Sims2*, SupCom*, Doom3, EQ2*, Planetside*
Late 90s-early noughties: Q3A, Carma2, Unreal, Morrowind*, GTA3, Daikatana, SiN
Mid-90s: Doom2, GP2*, Championship Manager, Quake
* = by reputation only, haven't played these myself
To be fair, some of these like Q3A, GTA3, Crysis and Unreal weren't necessarily bad engines or bad performers relative to graphical quality per se, just maybe a year or two ahead of their time so you needed to have the right kind of hardware.