Bowser, the King of Koopas and Mario’s primary antagonist, is a Bad Boss. Bowser, like Dr. Robonik, is actually a smart guy who makes unwise decisions that consistently backfire. The King of Koopas can take over the Mushroom Kingdom and any other land he wants using his vast army. Clearly he has to have some brains because Bowser military genius. He uses Goombas, Koopa Troopas, his one legitimate kid, and his illegitimate kids conquer and maintain dominance in these lands.
Bowser fails when it comes to actual one on one combat. In Super Mario Brothers, he hides the princess in the World 8 castle. This castle is a maze with many different obstacles that Mario must overcome. When Mario finds his way to the end of stage, Bowser is waiting at the other side of a bridge. The King of Koopas jumps while throwing fireballs and lots of hammers. Mario ducks under him and uses an ax to collapse the bridge and send Bowser into the lava. Why did Bowser build a bridge with an axe on it? Or why didn’t Bowser wait for Mario to cross the bridge halfway and then cut supports, sending Mario to a fiery and excruciating death?
Sometime later after the lava cools off, Bowser takes over eight different lands in Super Mario Brothers 3 using his children as foils for Mario. This time he gets a little more creative by having them use airships to get rid of that plumber. Mario surely jumps and stomps his way through these engineering marvels and eventually ends up at Bowser’s Castle. The King comes up with a brilliant plan by using his body to crush Mario. Unfortunately, every time Bowser came in for the kill, Mario would avoid contact. The King built this dungeon on a breakable floor and eventually he would crash through the floor and off to Parts Unknown. If he was smart, he would have used solid flooring and given Mario a smaller space to work with in order to crush him.
Bowser climbs out of the hole he’s created in order to do more planning. In Super Mario World, Bowser constructs a flying clown car and kidnaps the Princess. In the last battle of the game, Bowser attacks Mario using this vehicle and the large round balls that he dumps out of the vehicle. This is a great plan but then he screws up by throwing enemies that Mario can throw back at him. 
In Super Mario 64, Bowser takes over Princess Peach’s castle and Mario comes to the rescue. They fight several times in the game and Bowser doesn’t learn from these confrontations. In all the bouts, Mario and Bowser square off on a circular floor with bombs surrounding the perimeter. Bowser never uses these bombs against the plumber. These things don’t even hurt Mario if he runs near them. Mario grabs the King of Koopas by his tail, swings him like he weights nothing, and hurls him towards the bombs, defeating him once again. If there were no bombs, Bowser could have won but like all Bad Bosses he can’t close.
(Credit to VGMuseum.com for the pics.)
