This post contains SPOILERS for the Arrow season 5 finale and everything before. You have been warned. 

It has been about three weeks since the Arrow Season 5 finale ended with a bang, and I mean that quite literally. Lovable psychopath Adrian Chase/Prometheus completed his master plan by committing suicide and blowing up the island of Lian Yu, ostensibly with all of Oliver’s allies still on it. We know they are all still alive, but it was still a cool scene.

For Season 5 Chase put our hero through hell and then some and brought him to the brink physically and emotionally. But was he the greatest main villain the emerald archer has faced in the past five years? Wonder no more because redmangoreviews is going to be counting them down. Here are the top five Arrow big bads:

#5 Ra’s al Ghul (Matt Nable)

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You will sit here or I will scratch you with my pointy finger. And trust me, you don’t want me to scratch you with my pointy finger

I was excited to see iconic immortal Batman villain Ra’s al Ghul ever since they teased Nanda Parbat way back in Season 1. And Matt Nable certainly looked like the character with the great costuming. But he was just so, very, bland.

Now don’t get me wrong – the fight with Oliver on the snow-covered cliff was cool and him almost killing our hero was awesome. But everything else was just uninspired, from his monotone way of speaking, to his plan to make Oliver his heir (see the Batman comic story), to the forced marriage of Oliver and Nyssa, to the plan to destroy Gotham, sorry Star City, with a virus (see the plot of Batman Begins). Let us hope the Gotham TV series does a better job with their version of the character.

#4 Damien Darhk (Neal McDonough)

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Darhk: Just shut your mouth Soldier: But sir I… Darhk: I said shut it!

For Season 4 we had the magically powered and genocidal Damien Darhk. Neal McDonough played him as a smirking, over the top and slightly hammy villain and it kind of worked. Unlike the boring Ra’s at least Darhk had energy and was fun to watch. And the first time he used his powers to stop Arrow’s arrows mid-air was pretty dang cool.

Darhk will always be remembered for killing Laurel and trying to kill millions of people with nuclear weapons like a Bond villain. Side note: The character was even more interesting when he joined the Legion of Doom on Arrow’s sister show DC Legends of Tomorrow.

#3 Malcolm Merlyn (John Barrowman)

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You missed me by that much

In the United Kingdom John Barrowman is best known for his role as Captain Jack Harkness on iconic and long running science fiction series Doctor Who. And when he joined the cast of Arrow as the manipulative and calculating Malcolm Merlyn he made quite the splash on this side of the pond. He gave the character so much charm and wit and vibrancy that he made his presence felt in every scene.

Merlyn’s rooftop battle with Oliver in the Season 1 finale was 12 flavours of awesome sauce. His “Undertaking” to destroy the Glades with an earthquake device was a bit small potatoes though. And he became something of an anti-hero in his future appearances though at times he went full dark. Remember when he brainwashed Thea to kill Sara Lance? Not cool dude. But we are talking Malcolm as big bad and, while he was an enjoyable main villain, he only makes the bronze on this list.

#2 Slade Wilson/Deathstroke (Manu Bennett)

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What do you mean four fingers are pointing back at me?

One of the deadliest’s assassins in all of DC comics, Slade Wilson/Deathstroke was one of the greatest foes Oliver ever faced. We see in the flashbacks that the two began as allies on Lian Yu. But when Slade’s crush Shado is killed, partly due to Oliver’s inaction, and he (Slade) gets injected with super drug Mirakuru things start going downhill for their bromance. And Oliver did put an arrow through his right eye which is something not so easy to forgive.

Slade then engages in a campaign to destroy Oliver which included creating an army of Mirakuru soldiers and murdering Ollie’s mom right in front of him. As a big bad he was a physical threat to Oliver and we had the added dimension of their history together which gave more weight to their encounters. And his costume looked freaking cool. Slade Wilson was a fantastic main villain but he is narrowly beaten by our number one entry. Read on, dear reader. Read on.

#1 Simon Morrison/Adrian Chase/Prometheus (Josh Segarra)

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Can you hear me now? Good!

Just by process of elimination our number one entry will be on no surprise to anyone. And I know some of you will say “no way, Deathstroke is the best, you suck, worst list ever!” But please do hear me out.

When I first saw the mysterious Prometheus with his costume and arrows I was like “not another archery-based villain.” But little did I know what was waiting behind the mask! The reveal that district attorney and ostensible Oliver ally Adrian Chase was Prometheus was a gut punch. But that was merely the amuse-bouche to this five course meal of machinations and malevolence. Even after Oliver learned his identity Chase was all up in his face and walking around like normal and Green Arrow/Mayor Queen could do nothing about it. Now that is power. He is also a significant physical threat that can kill you as easily with a pen as with a sword.

You can call me, the Boogeyman!

Chase’s plan includes capturing, torturing and mentally abusing Oliver so much that he (Ollie) admits he loves killing and temporarily quits being Green Arrow. He once  tells Oliver he is 10 steps ahead of him and Oliver does not even know what game they are playing. And then he delivers on his threat by beating our hero at every, single turn. He tricks Oliver into killing Felicity’s beau, traps Oliver and Felicity in their own base, and also captures Ollie’s son and all his allies on Lian Yu. And then he kills himself in an effort to blow them up and prove a point. Now that is some Joker level crazy!

Ra’s was technically immortal, Darhk had magic and Deathstroke had Mirakuru strength but all Chase had was his brilliant, twisted mind and his fighting skills to bring the Green Arrow to his knees, which he did on several occassions. Hats, shoes and socks off to Josh Segarra for his mind-blowing performance of this psychopathic big bad and the number one big bad of the series so far.

So that’s my list. Who is your favourite Arrow big bad? Feel free to comment below.

For more Arrow action check out my review of the Season 4 finale here.