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- "I’ve seen that look before. When was it? Oh yeah, when you almost beat your only friend to death back at Excelsior." - Oliver Queen to Lex Luthor, Reunion
- "There's something seriously wrong with you?" - Oliver Queen to Lex Luthor, Reunion
However, by the time they were at high school at the Excelsior Academy in 1996, they had grown apart. Oliver and his friends Alden and Geoffrey bullied Lex and his only friend Duncan Allenmeyer. They pushed Lex down and teased him about being bald and ripped Duncan's comic book in half. When they caught Oliver and his friends stealing answers to a test, they argued about what to do with this newfound knowledge. Duncan wanted to report them, while Lex planned to blackmail Oliver. Eventually, Lex turned on Duncan to gain Oliver's acceptance. He started beating Duncan up, but was being so violent that Oliver had to pull him off him. Duncan ran away into the path of oncoming traffic. Believing he was dead, Oliver and Lex suffered with guilt as they grew up.
- "Well, it's a little hard to forget. Last time we met, you put an arrow in my chest." - Lex Luthor
- "You put a bullet in mine. Bygones?" - Green Arrow
When Oliver moved to Metropolis shortly after Dark Thursday, Lionel Luthor visited Oliver to welcome him to his new home. However, he had an ulterior motive. Due to the animosity between Lex and Oliver from their past relationship, when Lex disappears had Lionel suspect that Oliver was involved. Oliver claimed that he wasn't. However, it later turned out that he had hired Orlando Block and Wagner to kidnap Lex to discover the extent of his involvement in Dark Thursday.
Despite their past, Lex invited Oliver to his charity ball. However, Oliver went with Lois Lane when he bumped into Lex, they showed an obvious dislike to each other, much to Lois' surprise. They met again at Lex and Oliver's class reunion. Oliver's two friends died after the reunion and when Lois and Clark Kent investigated that deaths they uncovered Lex and Oliver's past and realized a hospitalized Duncan was behind the attacks through psychokinesis. Having been reminded of the past, Oliver decided to face his demons and confronted Lex but both blamed each other for what happened years ago at Excelsior. Clark saved them both from Duncan. Oliver then went to the Luthor Mansion to bury the hatchet and Lex thanked Oliver for saving him. Oliver admitted that he regretted ever bullying him and Duncan. Just as it looked like they could be friends, Lex responded by saying that he regretted ever thinking he needed friends like Oliver.
It wasn't long before Oliver and Lex were fighting again. This time due to their competitive relationship, both wanted to own Dr. Pamela Black's research on a drug that caused accelerated healing. Under the influence of the drug, Oliver flew into a rage and confronted Lex in his office. They argued, which resulted in them shooting each other. Oliver cured himself with the drug and when Clark arrives he also tried to inject the drug into Lex. Oliver's hatred for Lex became apparent when he tried to persuade Clark to let Lex die. Nevertheless, Clark saved Lex.
Oliver kept a close eye on Lex's activities and when he discovered Lex's experiments on meteor freaks, he assembled a team of superheroes (Arthur Curry, Victor Stone, Bart Allen and Clark) to help Oliver blow up one of Lex's facilities and then went on to continue to shut down Lex's operations across the globe, much to Lex's anger.
- "A terrorist? You really have it backwards. No one's ever been hurt. And Lex's factories aren't exactly producing Christmas toys for little girls and boys. I'm the good guy!" - Oliver Queen about Lex Luthor, Siren
Chloe Sullivan stayed in contact with Oliver while he was away and eventually Lex's illegal activities drew back Oliver to Smallville. While Lex was aware that Green Arrow was behind the attacks on his 33.1 experiments, he did not know that it was Oliver. Black Canary nearly revealed his identity, however, when Lex hired her to carry out his revenge on Green Arrow. Oliver was able to convince Black Canary of Lex's evil ways and the two confronted him together and got into a fight, which resulted in Lex getting injured.
- "Lex tried to kill me." - Oliver Queen on Lex Luthor, Requiem
After Lex's disappearance, Tess Mercer told Oliver about Lionel's involvement in Oliver's father's and mother's death, which upset Oliver. When he discovered Lex was still alive, he was eager to find him and get his revenge. Clark warned Oliver not to take out the sins of the father on the son and asked him to wait for him to deal with Lex. However, Oliver ignored this request and tracked Lex to Cuba. When he thought he saw Lex he shot an arrow directly at his head. However, it was only a doll.
When Oliver's Queen Industries merged with Tess' LuthorCorp, Lex hired Winslow Schott to plant a bomb in the board room to kill his rival. When the plan failed, Schott to another attempt on Oliver's life but Oliver was able to overpower him and steal the bomb. Oliver's desire to kill Lex only grew after this and managed to locate Lex and used Schott's bomb to cause a nasty truck explosion with Lex inside, killing him. He then took Lex's kryptonite ring.
After Lex was poisoned by Tess with a neurotoxin, his rivalry with Oliver were among his deleted memories.
Season Elevenhe was declared dead and before Tess's death. Lex angrily assures the public that he has not forgotten about Tess, and that he exiled himself from the outside world as a way of escaping the Luthor legacy. He then claims that he only returned because Tess called him before commiting suicide and the guilt of her death convinced him to recreate the Luthor image. Clark shows up and whispers to Lois that they both know Lex killed Tess, but can't do anything without proof. Lex then begins criticising Superman and the Justice League, claiming they have failed to protect humanity and now the world is in more danger than ever. He announces the Guardian orbital defense platforms as a means of protection and the public is impressed, save for Lois and Clark. She ask who will pilot the Shuttle to bring the satelites into orbit on such short notice, and Lex introduces the pilot, Commander Hank Henshaw.
50 Miles outside of Metropolis, 10 hours before the Luthorcorp shuttle takes flight, Lex watches the LuthorCorp shuttle in the distance, Oliver angrily confronts him, and warns him that the military will shut down his project, and that they knows just what he's capable of. Lex counters, asking if Oliver ever considered the military won't stop because of it. Oliver then counters, saying he knows what Lex is capable of, to which Lex claims he doesn't know, because of the loss of his memories. Oliver questions Lex on Tess's suicide, and Lex justifies it, claiming LuthorCorp's decline and the world almost ending caused her to do it.
Oliver denies his claims, and threatens to reveal that Lex killed Tess. Lex counters asking what would happen if he revealed Oliver was building a secret moon base for his team. Lex then ask Oliver about their friendship as teenagers, which Lex claims he's glad to have forgotten.
|Lex Luthor in Smallville|
|Oliver Queen in Smallville|