10. Turner D. Century
Clifford Michaels' father was worried his son would be tainted by the modern world's "degeneration of manners". As a result, he raised him in seclusion and forced him to embrace the morals of the early 20th century. After spending decades in isolation, Michaels ventured outside for the first time and was mortified by how "uncultured" the rest of the world seemed to be.
Michaels believed the only rational thing to do was to lead a movement to inspire humanity to embrace tradition. When that failed, he moved onto Plan B: become a supervillain called Turner D. Century, ride a flying tandem bicycle with a female mannequin, and attack nightclubs and bars with a fire umbrella.
The outdated outlaw tried to eliminate the corrupt youth by inventing a device that (somehow) kills anyone under the age of 65. In comics, there are countless examples of a villain preparing to activate a doomsday device, only to be stopped at the last second by a superhero.
But not Century. When the old-fashioned criminal turned on his machine, it... just didn't work, meaning he was defeated by his own incompetence. Maybe if he embraced 21st century tech, he could've built something just a little more threatening.