Assuming we're talking about 3-inch (or lightning flipper) games and ignoring the brutal 2-inch games from the 60s and earlier, I think my votes would have to go to:
EM:
Grand Prix (suicide lanes!), 300 (suicide lane!), Jacks Open (Slamming a very close target bank? Sure!), Flip Flop (bumpers that feed outlanes, 20 years before TZ did it!), Cherry Bell (this one is just stupid).
Early SS:
Flash Gordon (I don't think I ever feel safe on that game), Spectrum, Paragon, Eight Ball (Look ma! No left inlane/outlane!), Future Spa, Firepower (not hard in a good way).
Late SS:
F-14 Tomcat (Now you d-d-d-d-die!), High Speed, probably others that I'll think of later...
DMD:
The Shadow, BSD, Fish Tales (depends largely on the setup), Iron Man, CFTBL (pretty tricky multiball to score points in, plus no rubbers on the inlane/outlane posts from the factory!), NGG (how many times have you been shafted by a crappy kickout from the pops?), WCS (love those WPC95 coil stops).