Throughout its eight-season run, Arrow gave fans plenty of bad guys to develop a love/hate relationship with. Sometimes the audience just plain hated them. From mob bosses to metahumans, Team Arrow has seen it all and defeated them all. But the wins often came at a cost.
While some villains forever made their marks on the series and the fans, others fizzled out or never made an impression at all. When it came to Oliver Queen, some villains walked the line between enemy and ally. Here are five of the best, and five of the worst, villains on the show.
10 BEST: Brother Blood
Following the "Undertaking" event where the Glades were nearly demolished, Sebastian Blood became the Mayor of Starling City with the help of Slade Wilson. Working under Deathstroke, the leader of the Church of Blood agreed to acquire Mirakuru soldiers to destroy the city so that he could guide the city to salvation.
Brother Blood made a deal with a madman with a vendetta to create chaos that he had the power to stop. But he didn't account for Slade's obsession for Oliver Queen's blood. In the end, that blindness killed Brother Blood.
9 WORST: Malcolm Merlyn
Malcolm Merlyn used his influence and wealth to orchestrate a major terrorist attack against the Glades. Malcolm's motivations for attacking it stem from the death of his wife, who was killed by a thug from the neighborhood.
When his character returned with the plot of being Thea's real dad, he became obsessed with using her to get to the Arrow who thwarted him. If he'd been smarter and less myopic, he could have expended all that time and money on fixing systemic issues instead of trying to attack the symptoms.
8 BEST: Ra's al Ghul
The Head of the Demon led the League of Assassins and mentored Oliver. The back and forth of ally to enemy between him and Oliver made Ra's al Ghul a worthy villain. His dedication to the Demon eventually led to the fallout between him and his mentee.
Ra's looked for a successor as the Head of the Demon and he chose Oliver, but the Arrow declined. When it looked like Ra's al Ghul killed Oliver on the mountain top fight, the fans waited with bated breath.
7 WORST: Cupid
Carrie Cutter became obsessed with the Green Arrow and mimicked him by learning archery. She called herself Cupid as she believed she was in love with the vigilante. Where once she stopped crimes as part of the SCPD her obsession with the Arrow led her to commit them to get his attention.
Her manic obsession with a superhero that didn't even know her just made her seem like a lovesick school girl who went off the deep end. Her characterization didn't go far enough to show how she became that way.
6 BEST: Huntress
Helena Bertinelli was the daughter of Frank Bertinelli, a huge crime boss in Starling City. When he killed her fiance because he thought Michael was gathering evidence against him to turn into the FBI, she became a vigilante. She was dubbed the Huntress by Quentin Lance.
The Huntress made for a complex villain because she did the same as Oliver, go after bad guys. She also had a personal score to settle as it was her that had gathered evidence against her father's crimes, and her fiance paid the price.
5 WORST: Brie Larvan
The pun in this bad guy's name led to an even worse codename: the Bug-Eyed Bandit. Her superpower? Bees. Robotic bees to be exact. She controlled the mechanical bugs remotely to do her bidding. The first thing she did was exact revenge on her boss who fired her and the coworkers who ratted her out on her experiments.
Brie's overall characterization was cheesy and ridiculous. Granted, that is the nature of comic books and their characters. But considering the series had taken a darker tone than its source material, she just didn't fit right.
4 BEST: Damien Darhk
Damien Darhk once fought alongside the Ra's al Ghul in the League of Assassins, but he went rogue and started his own faction of the League called H.I.V.E. He took water from the Lazarus Pit to create the assassins he needed for his army.
He planned to implement a razed earth policy, in which he burned everything down to start the world anew. He built a following and they created bunkers to survive the apocalyptic event he had in mind. Team Arrow defeated him but lost the Black Canary, Laurel Lance.
3 WORST: Helix
The hacker organization founded by Cayden James was an obvious bad guy from the start, but Felicity Smoak was too blind to see it. Alena easily manipulated the Team Arrow tech expert, using Felicity's desire to do good against her.
But Cayden was not the same man he was before going into prison. He developed a plan to rid the world of its internet. Devastating as that might have been to social media junkies, it wasn't exactly an evil-genius level plan. When he attacked his follower Alena it proved he wasn't great at keeping allies.
2 BEST: Deathstroke
Slade Wilson was a member of the Australian Secret Intelligence Service who became one of Oliver's mentors after he survived the sinking of the Queen's Gambit. But when Oliver chose to save Sara Lance over Shado, Slade's paramour, he vowed vengeance against the vigilante.
The Mirakuru running through his veins didn't help Slade's judgment either. Deathstroke eventually made amends with Oliver, agreeing to help him take down Adrian Chase. At that point, all Slade wanted was to find and reconnect with his sons. He was a character that walked the line between villain and ally.
1 WORST: Prometheus
The former district attorney Adrian Chase feigned friendship with Oliver while secretly committing murder as Prometheus. The villain wanted revenge against Oliver for killing his father during his days as the Hood. When Oliver first started as a vigilante with no remorse for taking life, it wasn't his finest hour.
But Adrian's vendetta to expose Oliver as a murderer by murdering innocent people himself never made sense. Adrian just killed to get Oliver's attention rather than make an actual statement. He didn't end up being as intelligent a villain as he was made out to be.
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