The list bellow is a compilaton of near Legendary items I find to be both awesome and infuriating.
As you may or may not know, slender-man is a computer game with very bad graphics specifically made to make you get out of your chair and kick kittens in pure maddening rage.
Next to slenderman are characters known as spitters from a game called dead space 2. You wander through a dark corridor only to be encountered by a butt-hurt alien with the ability to grab you by the face and puke acid down to your intestines. This causes you to die and begin the 15 hour crusade all over again.
Bowser. The mear mention of his name brings both times of joy and hatred. Hatred of the option he alone carries. The option he carries is to take along with him a spiked tortoise shell that can be activated at anytime that tickles the users fancy. This shell destroys all chances of victory for the people in the top 3 of a race. Only scumbags and losers use this option. the joy comes from being the user and staring at the faces of defeat in the eyes of your friends.