Attacker: Richard Lawrence
Date: January 30, 1835
The odds of two separate guns misfiring one after another have to be slim, so clearly Richard Lawrence is some sort of special snowflake. When he attempted to assassinate then-President of the United States Andrew Jackson, that is just what happened. He shot at Jackson with one pistol that misfired, then tried again with another only to have that one misfire as well.
Jackson, not one to be shot at, advanced on Lawrence and beat him with his cane until Lawrence was apprehended. Bad. Ass.