Poor Oliver Queen might be the star of the hit CW series Arrow, but he never gets a break. Every time he breaks up a crime ring or helps Star City’s most unfortunate, it seems like somebody close to him gets an arrow in the eye, he finds out that he had a son (or two) many years ago, or his own personality flaws end up hurting people. Batman might have had a rough start, with his parents getting shot in front of him and all, but Oliver Queen has dealt with continuous physical and emotional beatings ever since the day he decided to stretch on green tights, and many of the terrible things that have happened to him are all his fault. It’s hard to be Green Arrow.

But what are the worst events that Oliver has faced? What were the occasions that really made him question himself, realign his goals, and become a different person — not always for the better? These answers aren’t for the faint of heart, but if you’re curious, these are the 15 Worst Things That Have Happened to Green Arrow.

15. He Got Stranded on Some Godforsaken Island

Green Arrow Year One3 The Worst Things That Have Happened To Green Arrow

Of course, the key event of Green Arrow’s origin is a pretty unfortunate one. If not for this, we wouldn’t be reading Green Arrow comics or watching Arrow on TV, because instead of slinging arrows at bad guys, Oliver Queen would instead be spending his days sipping cocktails on a yacht. As it turns out, boats ended up not being his friend.

There are different versions of the island story, but one thing is similar in each of them: unlike the castaways of Gilligan’s Island, Oliver Queen didn’t shipwreck with any friends, and learning how to survive in the island’s harsh environment changed him into someone dramatically different than the flippant wealthy socialite that he was before. From an early age, Oliver loves the story of Robin Hood, and has a childhood fascination with bows and arrows… but it’s not until he gets shipwrecked that he’s forced to rely on this skill just to eat and defend himself. Needless to say, going from a person who had taken all of his wealth for granted to a person who was lucky to make it from one day to the next creates a pretty dramatic — and traumatic — transformation.

The island Lian Yu has played a pretty big part of the TV series, with Lost-style flashbacks telling the story of how Oliver survived. While different retellings of the story have changed the details of the island’s environment, inhabitants, and so on, the fixture of the island itself has remained the integral component in Oliver’s backstory.

14. He Lost All of His Money

greenarrow money lost The Worst Things That Have Happened To Green Arrow

All of those Dark Knight homages in Arrow are, in a way, a form of tribute to the character’s earliest days. Back before he became the political icon he is today, Green Arrow had a lot in common with Batman. The original 1940s stories featured not just a red-shirted sidekick named Speedy, but also an Arrow-Cave, an Arrowcar, and he was even hailed to crime scenes through the use of an Arrow Signal. Another similarity between both Oliver Queen and Bruce Wayne are their massive inherited fortunes: though their reasons for fighting criminals are different, both have the luxury of enormous bank accounts.

When Denny O’Neal and Neil Adams took over the character in 1969, that all changed — and it’s also when the character finally took off and become a truly unique fixture in the DC Universe.

In the 1970s, Green Arrow became an outspoken progressive, constantly speaking up for minorities, the underprivileged, and any little people he felt were being left behind. As part of this character transformation, the storyline depicts all of Oliver Queen’s fortune being taken away from him, turning him into a working class hero instead of a billionaire. This massive loss is the result of corporate fraud by one of Queen Industries’ employees, John Deleon, who frames Oliver by forging papers that make it appear that he deliberately abused the city’s municipal bonds for his own profit.

13. He Had to Resign as Mayor

greenarrow mayor The Worst Things That Have Happened To Green Arrow

Some time later, after finding success as a newspaper journalist, Oliver runs for mayor of Star City. Though his mayoral bid fails to ignite the voting public, Oliver’s taste for politics, and his thirst for social justice, is not quenched, and he tries again many years later. This time, he wins the vote of the people, and though his popularity tends to hover around the 50% mark, he nonetheless finds great success in starting numerous new social aid organizations and helping the city’s income inequality. However, he also uses his political power to manipulate the stocks of immoral Star City corporations, and uses SWAT teams to aid his crime fighting activities.

Oliver’s political career ends in scandal, when his rival Brian Nudocerdo draws Oliver’s finances into the light, revealing that he’s been secretly funding the morally-questionable vigilante squad the Outsiders. Nudocerdo demands a recall election, and Oliver is forced to resign.

12. His Sidekick Became a Drug Addict

green lantern arrow The Worst Things That Have Happened To Green Arrow

While Green Arrow is a man who risks his life every day to defend the rights of others, both as Green Arrow and as Oliver Queen, one of his biggest flaws is that he often forgets to look over his shoulder and see what’s happening to the people close to him. Such is the case for Roy Harper, who began his vigilante career as Oliver’s sidekick, Speedy. From the beginning, Harper looks to Oliver as a father figure, but when Oliver leaves him behind to go on a road trip across the country with his buddy Hal Jordan, the Green Lantern, Roy becomes increasingly isolated. It’s during that this period that he tries heroin for the first time, eventually falling into the throes of addiction.

This would be bad enough, but Oliver’s response only made it worse: instead of being there for Roy, Oliver kicks him out to the street. Though Roy later overcomes his addiction and eventually becomes a teen drug counselor, this incident drives a wedge between Oliver and his former protégé that never fully heals. This was the first time that we saw Oliver’s poor parenting skills, but it wouldn’t be the last.

In the meantime, speaking of Hal Jordan…

11. He Had to Shoot His Best Friend

greenarrow parallax The Worst Things That Have Happened To Green Arrow

Oliver Queen’s closest friend and ally is Hal Jordan, the Green Lantern, and the two are a portrait of opposites: the outspoken, openly defiant, and aggressive Oliver Queen and the buttoned up, conservative space cop Hal Jordan make a strange team, but their road trip across the country sealed a tight bond for years to come. They’ve always been close, and always had each other’s backs.

Except for that time when Hal goes a little… off the deep end, and destroys the entire Green Lantern Corps.

When his hometown of Coast City is devastated by an alien attack, Hal goes understandably nuts, and then becomes possessed by the evil space entity known as Parallax. After wiping out the Green Lanterns and killing the Guardians, Hal decides to obliterate the entire universe, in order to then rebuild it in his image. Oliver doesn’t want to fight against his old friend, but when it becomes clear that there’s no talking Hal down, he’s forced the save the universe by firing an arrow into the former Green Lantern’s chest.

10. He Died

greenarrow death The Worst Things That Have Happened To Green Arrow

This might be higher up on the list, except Oliver does go out with a bang… and he comes back, anyway. Oliver is one of the rare characters to actually die, find his way into the afterlife, and then be brought back.

Basically, what happens is that Oliver is hired by the NSA, who then plants him as a mole inside a terrorist organization called the Eden Corps. His covert role in the Eden Corps puts him at odds with his Justice League allies, who are unaware that he’s undercover, until he’s able to gain enough trust within the organization to find out that they’re going to drop a bomb on Metropolis.

Oliver fights to prevent this catastrophe from occurring, but in the process he gets his arm stuck inside the bomb’s detonation chamber, resulting in a situation where the bomb will go off if he releases his arm. Superman tries to come to his aid, but can only free Oliver if he rips off his arm: with the clock ticking, and Oliver feeling that with only one arm he would have to give up the archery skills that he loves, he instead sets the bomb off in midair, saving Metropolis but sacrificing himself in the process.

9. In Another Reality, He Did Lose His Arm

greenarrow dkr The Worst Things That Have Happened To Green Arrow

In the Frank Miller classic The Dark Knight Returns, a comic book that deeply influenced Tim Burton’s Batman movies and many Batman depictions to date, Green Arrow plays a key role. The comic takes place in an alternate/possible future wherein Bruce Wayne retires from his role as the caped crusader, and Gotham becomes overrun with mutant gangs.

In DKR, Oliver Queen possesses only one arm, due to an earlier encounter with Superman — evidently in this reality, Oliver allowed Superman to tear his arm out of the detonation chamber rather than sacrificing his life, or perhaps Superman didn’t give him the choice. Whether or not this single decision created the paraellel reality that is DKR is up for the debate, since the comic depicts a rather untraditional vision of Superman. But what we do get to see for sure is that the Green Arrow in DKR, even with only one arm, is still pretty good with a bow and arrow, using his teeth to make up for the lacking digits.

8. He was Reborn… Without a Soul

Green Arrow Rebirth Oliver Queen Fortune Lost The Worst Things That Have Happened To Green Arrow

Anyway, back in the mainstream DCU Universe, Oliver Queen dies and goes to the afterlife. There he meets his old friend Hal Jordan, who goes on to become a figure called the Spectre, a metaphysical agent of divine vengeance. Hal Jordan wants to resurrect Oliver, but Oliver himself doesn’t want to go back, preferring his existence in Heaven. Eventually, the two come to an agreement wherein a version of Oliver will come back to the mortal world, and that it will be version of the Green Arrow that existed before he started killing people. The catch is that this version of Oliver will have no soul, so that the real Oliver’s soul can remain in the afterlife, enjoying whatever leisurely activities people enjoy in Heaven.

This soulless Green Arrow operates out of Star City for sometime, until he becomes aware of his strange condition. Later on, in a moment of crisis, Oliver’s soul is forced to return to his body, and begins life anew.

7. He Was Raped

greenarrow shado rape The Worst Things That Have Happened To Green Arrow

During his Longbow Hunters days, wherein Green Arrow moves to Seattle and begins using deadly real arrows instead of trick ones, he forms an uneasy alliance with Shado, a highly skilled archer and assassin played in Arrow by Celina Jade. In the comics, Shado is the daughter of a former Yakuza member who was tortured by Americans in a Japanese internment camp. After her family is murdered, Shado is trained by the Yakuza for the purpose of assassinating the men who destroyed her family, a path which eventually collides with that of Oliver Queen.

Later on, Green Arrow is blackmailed into tracking Shado down in Hawaii. When he finds her, Shado accidentally fires an arrow into his chest, leaving him badly injured. Shado nurses Oliver back to health, as he struggles to recover, his mind delirious from infection, pain, and the medications that Shado is giving him. During this highly vulnerable time, Shado rapes him. Oliver is too far gone to be aware of this action occuring, but he does call out the name of his girlfriend Dinah Lance, the Black Canary, causing Shado to stop. Regardless, by this point the union has already occurred, and Shado is pregnant.

6. He Accidentally Had a Couple of Kids (and Wasn’t There For Them)

greenarrow kids The Worst Things That Have Happened To Green Arrow

That’s right: Shado had his son. Though the child is named Robert Queen after Oliver’s father, Shado informs Oliver that he will have no part in the child’s raising. She holds true to this promise, even when Robert later develops cancer. The revelation of Oliver’s unintentional child with Shado understandably causes a lot of painful emotions for his girlfriend Black Canary, particularly since she had earlier told him that she didn’t want to bring children into the world, since the superheroic careers of their potential child’s parents might turn them into orphans.

However, Robert isn’t the only kid Oliver has kicking around. As it turns out, back in his good-for-nothing, party-going college years, Oliver fathered a son with his old girlfriend Sandray Moonday Hawke. Oliver initially doesn’t believe that she’s pregnant, but even after finding out the truth and holding his first son — Connor Hawke — for a single photograph, Oliver doesn’t want to be a part of the boy’s life; he opens a bank account for Sandra, funnels some of his vast fortune into it to help fund the boy’s upbringing, and then writes both of them off.

Years later, Oliver retreats to an ashram and comes face to face with Connor, who has been studying in the ashram for some time. Oliver dies shortly after this point, and in honor of his memory, Connor takes up the mantle of Green Arrow.

5. His Son was Put Into a Coma

greenarrow son coma connor The Worst Things That Have Happened To Green Arrow

After Oliver’s return from the dead, he and Connor move in together and begin forming a genuine father-son relationship, with Connor being amazingly forgiving of his father’s many past transgressions — needless to say, Connor is an exceptionally kind, accepting sort of guy. After Oliver and Dinah Lance finally tie the knot, Oliver is kidnapped, and then rescued by the heroic duo of his wife and son. But during the battle, Connor is shot by a toxin-coated bullet, and taken out of action.

Though Connor survives thanks to the fast intervention of the doctors and Hal Jordan, the poison on the bullet leaves Connor in a persistant vegetative state. With the doctors proclaiming that he’s unlikely to ever regain his full cognitive functions, Oliver is left with the terrible guilt of knowing that now, after finally kindling a relationship with the son he left behind as an infant, he may never have a true conversation with him again.

4. He Got Divorced

greenarrow black canary divorce The Worst Things That Have Happened To Green Arrow

Oliver Queen actually getting married is itself something of an achievement, since his philandering past is legendary, and his more recent mistakes have led to many breakups with Black Canary. However, when he and Dinah do finally say their vows, it’s a victorious moment, with almost all of their Justice League friends attending in costume. Even when a cadre of supervillains intervene, all of these bad guys are taken into custody, and Oliver and Dinah say “I do.”

As time goes on, Oliver estranges Dinah when he teams up with Green Lantern to form his own Justice League, employing harsher, morally questionable methods. Eventually, when Oliver begins hunting down and attempting to take out any allies of the supervillain Prometheus (more on him later), coming into conflict with the rest of the superhero community, Dinah returns his ring. Again, this isn’t the first time that Dinah breaks up with him, but it’s certainly the most impactful.

3. The Love of His Life Was Kidnapped and Tortured

greenarrow black canary torture The Worst Things That Have Happened To Green Arrow

However, the single darkest event to befall this couple occurs years beforehand, during a moment where their relationship is still strong. In Mike Grell’s Longbow Hunters miniseries, Oliver and Dinah move to Seattle, where they open the “Sherwood Florist” flower shop together, while individually each of them maintain their own separate vigilante careers. Dinah begins tracking down a local drug cartel, but in the process she is taken hostage, and brutally tortured.

Oliver desperately tries to find her, eventually finding her in an abandoned warehouse, where she’s been hung from the rafters and covered in blood. Right as one of her assailants is threatening her with disfigurement, Oliver shoots an arrow through his heart, killing him instantly. At this point Shado appears out of nowhere and comes to his aide, and the two of them rescue Dinah from the warehouse. Though she survives, the gruesome injuries that Dinah receives in this encounter rob her of her trademark “canary cry” powers.

This marks the first occasion that Green Arrow intentionally employs lethal force, with no remorse, and is perhaps one of the most important moments of the his career. From that point forward, Oliver becomes a more violent and unforgiving vigilante, not afraid to kill those he sees as irredeemable. It is likely that Mike Grell’s run on Green Arrow was the primary inspiration for the darker, more realistic, and more murderous depiction of the character seen in Arrow’s first season.

2. He Failed His City

greenarrow starcity The Worst Things That Have Happened To Green Arrow

Just like at the end of Arrow‘s first season, where Merlyn’s conspiracies result in massive destruction in the Glades, Oliver — despite his best efforts — has failed in protecting Star City from catastrophe. In the comics, the crisis in Star City is caused by Prometheus, a supervillain that menaces the entire Justice League, but he hits Green Arrow in a particularly personal way.

Prometheus is a sort of reverse Batman: a young boy whose criminal parents are shot dead by police officers,  and who thereafter vows to have revenge on all forms of justice. To achieve this, he trains across the world, becoming a brilliant mercenary and fighter, until he stumbles upon crazy alien tech that allows him access to an interstellar void called the Ghost Zone. Battling against the Justice League, Prometheus uses his advanced technology to threaten all of the Justice League’s distinctive cities simultaneously — and he makes good on his threat by destroying Star City. Saying that he will spare the other cities if he is released from custody, it is actually Green Arrow who convinces the other Leaguers to let him go… but only temporarily. Later on, Oliver tracks Prometheus back to his lair and kills him with an arrow between the eyes.

1. His Movie Was Cancelled. But If It Had Happened, He Would Have Gone to Prison, Anyway.

greenarrow supermax The Worst Things That Have Happened To Green Arrow

Between torture and citywide catastrophe, this is all pretty heavy stuff, so we’ll end on a somewhat lighter note: here in the real world, Green Arrow almost got the chance to join his compatriots Batman and Superman on the big screen… until the rug was yanked out from underneath him. Though Oliver Queen has become a well known figure on TV screens around the world, there are currently no plans to bring him into theaters anytime soon. However, many years before Stephen Amell first donned the emerald hood, a Green Arrow movie was in development. If he had made it to the movies, it wouldn’t have been a simple origin story — in fact, it would’ve had a lot more in common with Suicide Squad than what you might expect out of a Green Arrow movie.

Super Max, a script that was in development back in 2008 by David Goyer and Justin Marks, would have had Oliver Queen as Green Arrow for only the first ten minutes of the movie, until he is framed for murder, and then sent to a high security super prison modeled after Alcatraz. Stranded in Super Max without his trademark bow and arrows, Oliver would have to team up with an array of super powered bad guys to break out.

The film would’ve been an interesting deconstruction of the standard superhero movie format, but it never came together. In the long run, maybe it’s for the better. Green Arrow’s absence from movie theaters is probably what paved the way for Arrow to be such a breakout hit, and the series has brought the character a degree of mainstream popularity that he never had before.

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