As "Arrow" nears its 100th episode, it's hard not to look back at the plethora of evil beings that have made their way to Star(ling) City over the years, bringing violence, rage and seriously bad luck to Team Arrow and the citizens they try to protect.

As Season 5 brings two very big players to the baddie puzzle -- Prometheus and Tobias Church -- we wanted to take stock of the psychopaths and maniacs that led the way. Take a look below at five of the very best bad guys "Arrow" has ever seen.

5. Slade Wilson

It could be argued that Wilson (Manu Bennett) -- and his alter ego Deathstroke -- may be the big bad that has had the most impact on Oliver Queen (Stephen Amell). After all, he was with Oliver on Lian Yu and is responsible for a lot of his pre-Arrow training.

Of course, while they may have been allies at one point, that didn't last. Instead, Deathstroke became a true menace to Starling City. When last he was seen, Wilson was imprisoned back in Lian Yu in an ARGUS facility.

4. Count Vertigo

At first glance, Vertigo (Seth Gabel) may have just come across as your run of the mill drug dealer. He had much bigger plans, though. After surviving a lethal dose of his own drug -- administered by Oliver -- the Count came back bigger than ever, infecting a big portion of Starling City with his Vertigo drug.

However, once the Count's ways put Felicity in danger, Oliver had no choice but to stick him with arrows, leading to him falling out a window to his death.

3. Ra's al Ghul

Many have tried in vain to kill the Green Arrow. Ra's al Ghul (Matt Nable) is the one man to actually succeed. As the head of the demon -- the leader of the League of Assassins -- Ra's brought war to Oliver and all of Starling City. He killed Oliver via a sword to the chest -- or at least that's what they wanted you to believe.

He actually wanted Oliver to replace him as the head of the League. Instead, Oliver killed him.

2. Malcolm Merlyn

Malcolm (John Barrowman) is the adversary that just won't go away. Oliver has been plagued by Malcolm -- the father of his half-sister -- since the series began and he's only become more of a nuisance with each new appearance. What's worse, he's not always a bad guy. Sometimes his and the team's goals align -- for a little while, at least.

At the end of the day, Malcolm is only concerned with his own survival and power. He's a dangerous man to trust and just won't die.

1. Damien Darhk

The team has seen a lot of evil come through Star City. Never before -- and likely never again -- will they come up against a force as powerful as Darhk (Neal McDonough), though. Whereas many of the Green Arrow's most notable adversaries brought the fight to him, Damien didn't have to. He had magic on his side.

That left him practically impervious to just about anything the team could throw at him -- punches, arrows and bullets. He's also the man who killed Laurel Lance, with one of Oliver's own arrow no less. With Team Arrow's blood on his hands, there's no denying just how evil a force Damien Darhk was.

"Arrow" airs Wednesdays at 8 p.m. ET/PT on The CW.

Posted by:Chris E. Hayner

Chris E. Hayner is equal parts nerd, crazy person and coffee. He watches too much TV, knows more about pro wrestling than you do and remembers every single show from the TGIF lineup. You may have seen him as a pro-shark protester in "Sharknado 3." His eventual memoir will be called "You're Wrong, Here's Why..." TV words to live by: "I'm a firm believer that sometimes it's right to do the wrong thing."