Among the huge cast of characters that have appeared in The Simpsons, there have been some truly wonderful bad guys. From the murderous Sideshow Bob to the lovable mob boss Fat Tony; together they’ve been responsible for some of the most heinous crimes imaginable. When looking back across the show’s 32 seasons though, one character really stands out from the crowd.
He might not feature as much as he used to, but Mr. Burns has a long track record of causing chaos in Springfield. He steals, cares little for the environment, and is even willing to kill anyone standing in his way. Mr. Burns’ crimes are too numerous to count, but some of them are too villainous to ever forget.
10 He Used Lisa’s Lessons For Evil – The Old Man And The Lisa (S08E21)
When Mr. Burns realizes how unpopular he is with the youth of Springfield, he seeks the aid of Lisa in order to improve his image. While reluctant at first, she eventually agrees to help him and goes to great lengths to make him see the error of his ways.
Rather than use Lisa’s lessons to improve things though, Burns instead focuses on her explanation of how six pack holders can trap wildlife and sets up a new factory that uses millions of them to catch fish and other sea life.
9 He Dumps Nuclear Waste – Marge Vs. The Monorail (S04E12)
There are several instances throughout the series where radiation from the plant is evident, including the time when a three-eyed fish is discovered in one of Springfield’s rivers. Perhaps the worst example, however, can be found in the fantastic season 4 episode, Marge vs. the Monorail. It’s only a brief moment, but one which shows just how evil Mr. Burns really is.
When Smithers asks him whether they should dump the nuclear waste at the playground again, Burns mentions that the children who play there have started to lose their hair which is arousing suspicion. His solution? To dump the nuclear waste at the park instead.
8 He Shut Off The Town’s Power To End A Strike – Last Exit to Springfield (S04E17)
Working conditions at the nuclear power plant have never been great, but when Lisa needs braces and Homer finds out that the workers no longer have a dental plan, things really come to a head. Led by an irate Homer, the workers go on strike until Burns agrees to reinstate the plan. He’s not prepared to give up without a fight though.
Unable to force his employees back to work and unwilling to meet their demands, Burns turns off the power for the whole of Springfield. He does eventually turn it back on and even agrees to reinstate the dental plan as well, but not before Homer resigns as Union President.
7 He Tried To Bury Homer Alive – C.E. D’oh (S14E15)
Homer Simpson is far from the brightest bulb in the box, but every now and again he has been known to have some moments of pure genius. One such moment came in season 14 and led to him tricking Mr. Burns into handing over control of the Springfield Nuclear Power Plant.
Perhaps understandably, Burns doesn’t take too kindly to being hoodwinked and sets out to reclaim the plant. As it happens, Homer doesn’t much enjoy his new responsibilities and seems open to the idea of stepping down as C.E.O. Rather than taking the peaceful option though, Burns knocks Homer unconscious with a brick and then tries to seal him inside the Burns family mausoleum. He would have gotten away with it too if he did not take a ridiculous amount of time to seal the exit.
6 He Stole The Simpsons’ Puppies – Two Dozen And One Greyhounds (S06E21)
When Santa’s Little Helper falls in love with a female greyhound at the Springfield racetrack, her wealthy owner allows the Simpson family to keep her. It doesn’t take long for She’s the Fastest (who completely disappears after this episode) to fall pregnant and the family soon find themselves with 25 little greyhound puppies to take care of.
Although they try their hardest to make things work, it soon becomes clear that the puppies will need to be re-homed. Before a suitable home can be found though, Mr. Burns ends up stealing the pups and with a view to skinning them to create a greyhound tuxedo. He doesn’t go through with it in the end, but that’s largely down to Bart and Lisa’s intervention.
5 He Stole A Trillion Dollars – The Trouble with Trillions (S09E20)
Following the events of World War 2, America printed a one trillion dollar bill which was to be given to the allies as financial aid. The man chosen to deliver this small fortune was none other than Charles Montgomery Burns. The reasoning for this decision was that as America’s most wealthy citizen he should also be the least likely to steal it. Clearly, they didn’t do their research.
Many years later and with the FBI closing in on the bill’s location, Burns, Homer, and Smithers take the money to Cuba in order to start a new life. However, things don’t go entirely to plan and while trying to buy the island, Burns ends up handing the money over to Castro. Upon returning to the states, he is put on trial but uses his wealth to bribe the jury and escape without consequence.
4 He Tried To Turn Bart Against His Family – Burns’ Heir (S05E18)
After a close brush with death, Mr. Burns realizes that he doesn’t have an heir (apparently he forgot about Larry) and decides that it’s time to create a nuclear family of his own. He organizes a competition that allows him to pick out his ideal heir but eventually settles on Bart after the young troublemaker reacts poorly to Burns’ initial rejection.
Things start out okay, but after a while, the twisted billionaire starts trying to manipulate Bart into leaving his family. As well as trying to pressure his new heir into firing Homer from the plant, Burns even goes as far as hiring a team of actors in an attempt to trick Bart into thinking that his family no longer cares about him.
3 He Tried To Seduce Marge – Marge Gets A Job (S04E07)
When the Simpsons discover that their house is sinking, Marge is forced to get a job at the power plant in order to help finance the expensive repairs. It doesn’t take long at all for the new recruit to start attracting the interest of the plant’s management. Unfortunately, however, it’s for all the wrong reasons.
After spurning Mr. Burns’ inappropriate advances, Marge finds herself out of a job and hires the ever-incompetent Lionel Hutz to take her former boss to court. Rather than simply admit to his misdeeds though, Burns hires a team of expensive lawyers to intimidate Hutz and make the case go away.
2 He Blocked Out The Sun – Who Shot Mr. Burns? Part II (S06E25)
The season six finale Who Shot Mr. Burns? Part I features the titular character at his absolute worst. After failing to coerce Principal Skinner into handing over the school’s newly discovered oil reserves, Mr. Burns decides to steal the oil instead. Not only does this lead to several people losing their jobs, but also Santa’s Little Helper getting seriously injured. Burns even tries to steal candy from a baby, although this doesn’t prove to be as simple as he’d first imagined.
This is all just the tip of the iceberg, however, as stealing the oil is only the first part of Burns’ master plan. Next, he uses a mechanical device to block out the sun and plunge Springfield into a state of eternal darkness. By doing so, Burns ensures that the townspeople will have to rely on his nuclear power if they wish to free themselves from this permanent nighttime.
1 He Tried To Murder Grandpa And Bart – The Curse Of The Flying Hellfish (S07E22)
Considering his immense wealth, it’s perhaps a little surprising that Mr. Burns served in World War 2 rather than buying his way out. What’s less surprising, though, is that he was an insufferable tool even back then. In season seven, viewers learn that Burns actually belonged to a squadron known as The Flying Hellfish and served beneath Grandpa for several years.
As the war was winding down, the squadron stole a selection of high-value paintings and came to an agreement that the last surviving member would take possession of the haul. When Asa Phelps dies and leaves Burns and Grandpa as the last remaining members, the former tries to kill both Grandpa and Bart in order to get his hands on the hidden cache of artwork a little bit sooner.
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