Oliver's parents traveled frequently and extensively when he was young, associated in business and in research with the Teague, Swann and Luthor families. They died on October 14, 1989. En route to visit a prominent politician in Seoul, their plane was sabotaged and crashed into the ocean. Oliver was in the fourth grade, around age 9 or 10 at the time. Oliver attended Excelsior Academy with Lex Luthor in the 1990s. He graduated in 1998 and deferred admission to an Ivy League school to sail away in a private yacht to say goodbye to his parents. However, his crew attempted to murder him and steal his yacht. Oliver used his limited archery skills to escape onto an inflatable life raft, but the crew sailed away in his boat, leaving him in the middle of the stormy, shark-infested ocean.

Oliver washed up on an island and was stranded for twenty days before encountering the island's natives. He lived among them for over three months during which time they taught him how to hunt and improved his archery skills. Upon further exploration, Oliver was shocked to discover the wreckage of his parents' plane on the island. He collected their wedding rings from their remains and also found a letter his mother had written to him the night of the crash. Serendipitously, Oliver's stolen yacht also banked on the island eleven months after his arrival. Oliver resolved to get it back; he and the natives staged a coup and Oliver was able to reclaim his boat and return to his home, Star City, where he began fighting crime in the city as the Green Arrow.

During his time in Metropolis, Oliver lived in a loft apartment known as Queen Tower. His company, Queen Industries, owned the only satellite that stayed online during Dark Thursday and Oliver learned that Lex was behind the destruction. He had Lex followed and kidnapped so he could be questioned about the origins of his powers. Lionel suspected he was responsible and showed up at his loft. Oliver found him there and denied having anything to do with it. Something to keep in mind, however, is that Oliver specifically ordered his men not to use any type of violence unless they were in danger. It is possible that Lex was being "scouted" as a possible member of the Justice League, or else he was being evaluated as a potential enemy. Either way, Oliver realized that Lex's powers were gone and his interest seemed to have done the same.

Oliver donned his Green Arrow uniform and stole a diamond necklace from Martha Kent. Lois Lane became obsessed with finding the identity of the green thief, which got her kidnapped by his enemies. They tortured her to force her to provide information, but he rescued her in time. She attempted to unmask him, but Clark Kent intervened, in exchange for return of the diamond necklace, and the two agreed to protect each others' secret identities. However, Oliver was unimpressed with Clark; he believed Clark should use his powers to help anybody in need.

Lex and Oliver returned to their school for an alumni event and were startled when Oliver's old friends were killed in violent and mysterious accidents. It was revealed that Oliver and his friends relentlessly teased Lex and his best friend Duncan Allenmeyer, eventually goading Lex into beating Duncan up and causing him to become severely injured in a car accident. Oliver believed that Duncan had died, but the recent murders began to point to him. Oliver had to face the guilt and regret over his part in Duncan's severe injury and admitted to Lex that he was sorry. However, Duncan had, in fact, survived and almost killed Oliver in revenge, but he was saved by Clark Kent.

Oliver had Dr. Pamela Black manufacture a healing drug. In the middle of a date with Lois, Oliver dashed away to save a couple from being carjacked, but was shot in the process. He used the drug to heal his wound completely. However, it also had side effects: angry outbursts and mood swings. When Clark went to see if he was all right, he insulted him and ordered him to leave him alone. Lois came into the apartment and saw him there, dressed as the Green Arrow. He pushed her down into a glass table and fled. He went to find his shooter and discovered he had obtained the drug from a LuthorCorp halfway house. Oliver attacked Lex with an arrow and Lex shot him in the chest. He took the drug again to save his life and Clark gave Lex the drug to save him.

Oliver had been recruiting super-powered individuals to form a group that fought for good. His band of super-human heroes then had to spring into action and rescue team member Impulse. They worked together to destroy one of LuthorCorp's Level 33.1 facilities. He and the Justice League left Metropolis to shut down other Level 33.1 locations across the globe.

Once Oliver returned, he asked Chloe for help to download information on Lex’s projects, and once she did, she was attacked by Black Canary. Oliver managed to get to her in time to save her, although Clark later showed up in his apartment with angry words for getting Chloe involved with Oliver. He figured Lois would be there to see him so he made dinner for them, however, Black Canary appeared, and attacked them. After the attack, Lois saw Green Arrow’s gear and discovered he was Green Arrow. Oliver later got loose, and had an intense fight with Lex. He then asked Lois to try to make their relationship work, but she knew it was not going to work out. Although, he did make an addition to his team of heroes: Black Canary.