Handing you your ass in: Sonic 2 (Game Gear version)

Sonic 2 on the Game Gear was seriously tough. The reactions and speed of thought that were required to manoeuvre the mammal through the game were completely hampered by the zoomed-in camera, small screen and dreadful D-pad. The first level doesn't pull any punches in helping you to acclimatise either, immediately throwing you into a rollercoaster of slopes, pits of fire and a bitter betrayal by a boss.

It all kicks off at the end of the first stage as you start to plummet to a fiery death. With the end in sight, your thoughts start to ponder that eternal question ‘do all good hogs go to heaven?’. But before Sonic becomes stew your arch nemesis saves the day with his flying contraption. Aww shucks, Doc. We never knew you cared. Just as we start to think Robotnik and Sonic are set to start making holiday plans together, though, the portly professor drops you at the pincers of one pissed off lobster thing.

The excruciating equation:

We don’t mind bosses who are upfront about wanting to kick you in the face, eviscerate you or give you a thorough gutting. But a boss who’ll lull you into a false sense of security before lobbing you to the lions(or in this case chucking you to a crustacean)? Now that is low. Not only to you have to stop yourself from becoming lobster lunch, but you’ve got to avoid the Doctor's balls of death…erm, so to speak. Requiring the kind of quick reflexes that would cause the early onset of arthritis on the Gear’s clunky D-pad, this is a despicable combination of deception and death-defying jumping skills. And all on the first level too. For shame Eggman. For shame.

Inexplicably harder than: Speeding past Shamu. Somehow it’s easier to outrun 8 tons of 128 bit orca in Sonic Adventure than avoid the pixelated pincers of this pathetic crab creature.

Above: The bottom image may not look that tough, but the searing speed on the small screen makes crippling this crab harder than any SeaWorld-sponsored sprint

Handing you your ass in: Driver

What better way to prepare you for French Connection-esque chases from the cops than the world’s hardest tutorial. Not only do you have to complete a series of unexplained objectives with no prompts as to how to pull them off, but you have to do it all under a tight time limit too. It’s a truly torturous tutorial and trying to pull off a reverse 180° with seconds to go is like trying to make a house of cards while standing on a bed of hot coal.

The excruciating equation:

Performing a slalom has to take the needlessly convoluted cake, though. How the hell are you supposed to know you need to drive around a row of pillars twice? We’re all for figuring things out for ourselves, but this is akin to being pitted at the bottom of Everest with only toothpicks to scale your way back to the summit. And unless the cops are suddenly going to start to weave between lamp-posts in a comedy Benny Hill-style car chase, it’s a fairly useless skill to learn in the first place. It’s utter Madness as they say, as we amply demonstrate with our miserable motoring skills below.

Inexplicably harder than: Careening off a massive stunt jump in GTA IV while your bonnet is lit like a bonfire.