Oliver Queen a.k.a. the Green Arrow had a very complicated time while he was alive in the Arrowverse. With Arrow having concluded earlier this year, reflecting on Oliver’s massive journey is one that easily takes you down a rabbit hole. While Oliver became a champion of the entire franchise, as he literally gave his life to reboot the Multiverse, this version of the Emerald Archer is definitely a controversial one.

For everything good he has done in 8 years, Oliver has most certainly had moments where he was at his worse. Given how many of his ups and downs there are, it’s a miracle that Oliver survived for as long as he did. These are 5 times when we felt bad for Oliver as well as 5 moments where he was absolutely the worst.

10 Felt Bad For Oliver: Seeing His Mother Murdered

The second season had Oliver go up against Deathstroke who had a vendetta against Star City’s protector. One of his ultimate moves is when Deathstroke kidnaps the entire Queen family and has them tied up in the woods.

He wasn’t ready for Oliver to die, because Slade Wilson wanted him to be alive for when he executed his mother. Despite trying to plead with him, Moira is executed by Slade in front of Oliver and Thea. Despite Crisis undoing her death, having to see his mother murdered in front of him was something not even Oliver deserved.

9 Hated Oliver: Cheating On Laurel With Her Sister

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While Black Canary and Green Arrow are a power couple in the comics, The CW version never went in that direction. While Laurel Lance and Oliver did have a romance back in the days, the playboy billionaire naturally screwed it up.

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Even though Oliver was stuck in hell for 5 years, it doesn’t change the fact that he literally cheated on Laurel with none other than her little sister. The pain that it caused Laurel just makes Oliver the worst boyfriend ever.

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8 Felt Bad For Oliver: Watching Lian Yu Blow Up

Prometheus is and always will be one of the best villains that Arrow has ever brought to life. The season 5 finale became one of the best conclusions to any season of the entire series. After having put Oliver and his team through hell, Adrian Chase proceeds to his final step as he gets all of Green Arrow’s allies and loved ones trapped on Lian Yu.

While Oliver manages to get William back during a boat battle, Adrian shoots himself and triggers the dead-man switch as Oliver and William watch the island get destroyed.

7 Hated Oliver: Shooting An Arrow At Roy’s Knee

While Roy Harper is one of Oliver’s closest allies in the comics, the TV show took its time to get them there. At their best, they were more frenemies than anything, especially in the first two seasons.

During Roy’s path to try to become a hero like The Arrow, Oliver gets sick of him constantly defying him. Because of that, Oliver does what any unstable person would do by shooting an arrow into Roy’s knee.

6 Felt Bad For Oliver: Losing Tommy

The season 1 finale was a game-changer for the series going forward as Oliver went into his biggest battle yet against the Dark Archer. However, he also had to suffer a tremendous loss. During the leveling of the Glades, Laurel gets trapped inside the building where she works before Tommy Merlyn manages to save her.

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But it would end up costing him his life as he gets pierced by a metal bar and he ends up dying in front of Oliver. Despite Crisis undoing Tommy’s death too, Oliver having to witness his best friend die was still heartbreaking.

5 Hated Oliver: Hiding William’s Existence From Felicity

It’s a miracle that Oliver and Felicity Smoak somehow ended up together because the amount of secret-keeping between those two was exhausting. One of those times was when Oliver discovered that he had a son in Central City.

But Oliver is only allowed to see William regularly if he doesn’t tell anyone about his existence, even girlfriend. The fact that Oliver didn’t think Felicity could keep it a secret was one of his worst moments of all time.

4 Felt Bad For Oliver: Finding Thea Almost Close To Death

Following the destruction of Lian Yu, Oliver goes through a nightmare as he tries to find survivors. But things get emotional when he discovers his little sister’s unconscious body.

As Thea has been close to dying before, Oliver breaks down as this was another time where she was close to death taking her. Thankfully, Thea survived, but it’s still traumatic as she was in a coma for months after that.

3 Hated Oliver: Not Telling Barry & Kara About The Deal

Oliver’s role became set in stone for Crisis on Infinite Earths after he had made a deal with The Monitor in the Elseworlds crossover to spare Barry Allen and Kara Danvers’ lives.

In exchange for that, Oliver’s life would be taken during the Crisis. As understandable as it was that he didn’t want to burden them, Oliver should have still been open with them.

2 Felt Bad For Oliver: Having To Die Twice In One Crossover

The first hour of the 5-part crossover had Oliver pass away in the closing moments of the episode. But as if one death wasn’t enough, Oliver had to ultimately die twice in his final crossover.

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The second time was after he had used his Spectre energy to reboot the Multiverse. Having to die not once, but twice in one crossover is not something every superhero goes through.

1 Hated Oliver: Hooking Up With Sara… Again

After Oliver had returned to Star City to become the Emerald Archer, it took only a season for Sara to eventually return home too, as The Canary. But as the two struggled with being in each other’s lives again, they, unfortunately, overcame it.

By the second half of season 2, Oliver and Sara were once again hooking up. Despite the fact that this is what caused Laurel all that pain, to begin with, Oliver and Sara were just that selfish.

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