Since the moment he came back to Starling City Oliver Queen has been different. He changed from spoiled playboy to hardened killer. Over the first five seasons, we got flashbacks into his life to see how he became a ruthless vigilante. We’ve also gotten to see how those experiences have translated into his new role as the Hood/Arrow/Green Arrow. Oliver is the kind of hero who believes the ends justify the means. He will do whatever it takes to help the greater good. If he needs to torture or kill a few criminals to save a city full of innocent people, he won’t hesitate.
The hard truth about Oliver Queen is that he’s actually deadlier than the bad guys he faces off against. Sure Ra’s al Ghul and Damien Darhk had to be killed to save the world, but that doesn’t explain the murders of drug dealers, businessmen and henchmen following orders. Come on, some of those guys had to just be people in a tough spot with no good choices, until a vigilante came along and seriously injured or murdered them. With that in mind, these are the brutal and violent scenes that prove Oliver is worse than the villains he fights.
15 SHOT BARRY WITH AN ARROW
Even before he knew Oliver was the Arrow, Barry was star struck with the popular playboy. Barry was the dorky nerd in love with his best friend and Oliver was the handsome billionaire who it seemed had the perfect life. Once he found out Oliver was also the Arrow, he became even more of a fanboy. They may have butted heads at first, but they eventually came to an understanding.
When Barry became The Flash, he jumped into superhero work very quickly. During their first team up Barry needed to learn that there was plenty he still didn’t know about crime fighting. Oliver obliged by showing him how to scout his surroundings. He used one of his greatest hits, shooting a new friend in the leg. Yes, he did it to protect Barry from getting hurt in a real situation, but that didn’t make Barry’s leg feel better.
14 TORTURED GENERAL SHRIEVE
His time in Hong Kong was particularly tough for Oliver. Though he honed the skills that would make him the Hood in Russia, this is where he started down the path. He was tasked by Amanda Waller to stop a bioweapon outbreak. Unfortunately, he was unsuccessful and his young friend Akio was killed. Oliver blamed General Shrieve (as he should have since he released the virus), and took his time torturing him with arrows.
This is the moment at the end of season three where he realizes he’s changed and can’t go home. It’s also the first time he says someone has failed this city. This is basically the birth of the monster he sees himself as. Shrieve was evil and deserved what he got, but this is where Oliver made the choice to start down his complicated path.
13 CUT OFF MALCOLM’S HAND
Look, no one is crying any tears for Malcolm Merlyn’s hand. He chose the power of being Ra’s al Ghul over saving his daughter’s life. He could have easily given control of the League over to Nyssa and everything would have been fine. However, he put this whole situation in motion, so he suffered the consequences.
As far as Oliver is concerned, he was in a horrible position and just wanted to find a way to save Thea. It’s just that all this happened when he was trying to figure out the best balance between being Green Arrow and Oliver Queen. While it was a non-lethal solution to everyone’s problems, you know he enjoyed cutting off Malcolm’s hand after everything he had done to the Queen family and Star City.
12 INTERROGATED HIS MOTHER AS THE HOOD
From the moment Oliver came home from the island he could sense something was off about his mom. He couldn’t quite figure out if it was just the awkwardness of his return or a more mysterious reason. After some investigating by Diggle, it became clear that he had questions his mother had the answers to.
Instead of sitting down to have an adult conversation where he confronts her about all her lies, he put on his Hood and crashed through her window, terrifying her, then questioning her. This became a regular issue for the Queen family. Lies festering, until they explode at the most inopportune time. The one silver lining from this moment was that when Moira shot Oliver he was forced to reveal his identity to IT’s Felicity Smoak.
11 TORTURED SOMEONE FOR THE FIRST TIME IN HONG KONG
Like a lot of DC characters, Oliver can trace his worst decisions back to Amanda Waller. She brought him to Hong Kong to stop a deadly virus from being released. The first stop to discovering her plan was to interrogate one of her associates. After his initial failure to torture someone led to a bomb killing innocent people, Oliver didn’t hesitate the second time around.
Though everything happened off-screen, it was evident that Oliver was disgusted with himself and couldn’t believe the line he had just crossed. With General Shrieve he’s making the choice to continue down a road he’s already on. Here is where he takes the first steps in that direction. Though, he regretted it, this is the moment where Oliver learns what it will take to live in the same world as the criminals he hunts.
10 KILLED KOVAR’S ACCOUNTANT IN RUSSIAN JAIL
Oliver’s promise to take down Konstantin Kovar meant he had to join the Bratva. This led to him making a lot of shady vows that had deadly consequences. Anatoly explained several times that being in the Bratva was about trust, so when he told Oliver to go to jail, get information from one of Kovar’s men and then kill him; he obliged.
Turns out this guy was basically just an accountant who was laundering Kovar’s money. You have to imagine he had no choice in working for the biggest crime boss in Russia. Oliver threatened his wife and child, then broke his neck without giving it a second thought. He did yell at Anatoly about it later, but he didn’t really feel bad. The poor guy was essentially a necessary evil to getting Kovar.
9 BEAT UP NEW TEAM WHILE TRAINING THEM
Obviously vigilante work isn’t easy. It requires an impossible amount of physical skill. With his team of Diggle, Roy, Laurel, Thea and Felicity, Oliver knew he could count on them to have his back. Once they went their separate ways he needed a new team to help him save the city.
Starting from scratch he recruited Rene, Evelyn and Curtis to be his new back up. Using methods he learned from the Bratva probably wasn’t the best choice for training. An exercise called “ring the bell” involved the new recruits trying to make it past Oliver to ring a bell. It was supposed to be about teamwork and trust, but it really just led to Oliver beating up on the new kids. Of course, in the end it did make them a stronger team.
8 SHOT ROY IN THE LEG
After he saved Roy from a copycat vigilante, Roy became obsessed with finding out the identity of the Hood. Though it was a while before he found out it was Oliver, Roy still wanted to help him with his work. He tried to stop a few small time crimes, but wasn’t really prepared at that point. To save him from himself, Oliver shot Roy in the leg. Shooting his friends in the leg is kind of Oliver’s jam. Just ask Barry and Rene.
Perhaps, if he had just started training Roy the minute he asked, he would have saved him from being captured by Brother Blood and injected with Mirakuru. Oliver taught Roy a lot and if asked Roy will say nothing but great things about his mentor, however this wasn’t Oliver’s greatest teachable moment.
7 LEFT EVELYN TO BE PRESUMABLY KILLED ON LIAN YU
Oliver doesn’t trust easy. After his first team went their separate ways, it was incredibly hard for him to bring new members into the fold. Reluctantly he did, recruiting Rene, Evelyn and Curtis. Unfortunately, Evelyn proved herself to be the unstable, untrustworthy person viewers assumed her to be when she turned on the team and joined Prometheus.
In the epic season five finale, Evelyn was on Lian Yu with the rest of the villains, but she was captured and locked up in a cell in the middle of the island before the big showdown. Then there was the explosion and no one ever saw her again. Granted there was a lot going on at the time and everything was on fire, but knowing how responsible he feels for everyone, it’s out of character that Oliver never mentioned also trying to save Evelyn.
6 KILLED THEA’S DRUG DEALER
Thea did not handle losing her father and her brother well. She spiraled into drug use to compensate for being left on her own. As part of his mission in Hong Kong, Oliver was forced to return to Starling City without letting anyone know he was there. While he was stalking around town he discovered what dire shape his sister was in.
At one point he runs into Thea’s sketchy dealer and to protect his secret and stop her drug use he kills the guy. It’s true this guy was awful and was ready to tell everyone he was alive, but was there really no other way to solve that situation? Oliver didn’t know his life or what led him to dealing drugs. It was another indication of how much Oliver had changed from that helpless guy in season one.
5 KILLED BILLY MALONE
In season five Prometheus was several steps ahead of Team Arrow the entire time. If they seemed like they were figuring things out, it was because he wanted them to. This was never more true than when they thought they had tracked Prometheus to his warehouse hideout. Unfortunately, it was all part of his plan and Oliver was tricked into killing Detective Billy Malone.
While shooting Billy isn’t all Oliver’s fault, he is the one who fired the arrows so he has to take some responsibility. Plus, you know he feels extra guilty for killing Felicity’s new boyfriend and breaking her heart. This is a situation where Oliver’s lust for revenge didn’t allow him to think things through and poor Billy paid the price.
4 TORTURED A CRIMINAL RIGHT IN FRONT OF BARRY
From the moment he discovered he had superpowers Barry knew he would become a hero like Oliver. When he was initially unsure of himself, it was Oliver who gave him the confidence to continue by telling Barry he would be a better hero than him. That conversation sparked a special mentor/protege bond. Oliver has always been Barry’s role model.
Once they finally got to team up, Barry’s friends questioned whether he should work with the Arrow because he was known as a much rougher crime fighter than Barry. Turns out they were right, because Oliver wasted no time in torturing the first bad guy they came across. Barry was shocked and appalled, and it completely changed what he thought of Oliver. Their friendship is in a great place now, but this is when Barry realized the toll superhero work actually takes on a person.
3 KILLED CORRUPT BUSINESSMEN WHEN HE CAME HOME
Upon his return to Starling City, Oliver had one plan; to right all the wrongs his father couldn’t fix. He had a list of all the corrupt business people in town and checked them off one at time. He would show up kill a few of their security people (who were just trying to get a paycheck) to make a point and then demand that the offending crime be corrected. Of course, most powerful people weren’t interested in negotiating, and things usually ended with deadly arrows.
Yes, these men were terrible people who didn’t care about who they hurt, but did they all deserve to die? As a matter of fact, his first few murders made the others on the list even more ruthless, so his tactics were actually counterproductive. The whole plan was crazy and ineffective from the start.
2 KIDNAPPED LYLA
Oliver has a bad habit of coming up with a plan and not informing others on his team about it. It’s his biggest weakness and leads to a lot of fights. Never was this more dangerous than when he was trying to destroy the League of Assassins and Ra’s al Ghul. Oliver let everyone believe that he accepted Ra’s offer to become the next leader of the League. As part of this plan, he kidnapped Lyla to trade for Nyssa.
Though none of us knew it at the time, he had good intentions and wasn’t going to hurt Nyssa. However, it still crossed a line between him and John. Lyla and John are experienced operators and would have understood if he had just told them what was going on. On a long list of violations of trust, this is Oliver’s worst.
1 TORTURED A CRIMINAL IN RUSSIA FOR PRACTICE
Russia was Oliver’s last stop before he came back to Starling City. It was here that he truly became the vigilante. His time with the Bratva and training with Talia al Ghul were the last pushes needed to allow himself to accept who he was on the inside.
He decided if he gave his dark side an identity, he would be able to use it for whatever purpose he needed. Kovar was planning a nerve gas attack and the Bratva wanted to know how to stop it. Oliver interrogated one of Kovar’s men in a terrifying manner that even Anatoly found disgusting. Once finished Oliver told him, “he gave up pretty quickly, the rest was just me practicing.” That was the exact moment that Oliver became the Hood and it became very clear all that he was really capable of.