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Oliver and Jimmy did not have any interaction at this time. At the time both were dating Lois Lane and Chloe Sullivan respectively. Jimmy began to work on a story with Lois in an attempt to discover Green Arrow's identity, who unknown to them was Oliver. Jimmy sold Lois some photos he took of the Arrow that showed that his arm had been cut. Lois later noticed a similar cut on Oliver's arm and began to suspect Oliver as being the Green Arrow. Lois asked for Jimmy's help in a stint to reveal the Arrow's identity. She pretended to be chased by thugs in an ally way and then was approached by real thugs. Jimmy came out to help Lois against the thugs but had overtaken them. Then Green Arrow showed and shot of his arrows and threw one of the thugs straight across the ally way. Lois then said that to the Arrow "Your secret is safe with me Oliver" and proceeded to kiss. Jimmy took some snapshots and then Oliver showed up to everyone's surprise. Jimmy tried to take a shot of the "Arrow's" face but superspeed away before he could. Clark Kent was later revealed to be impersonating Green Arrow in order to protect Oliver's secret. Later that night Jimmy excited went to the Daily Planet to show Chloe the photos he took. He started off by showing Chloe the pictures of Lois kissing the "Arrow" and Jimmy remarked that he felt bad for Oliver when he saw that. Jimmy then tried to show Chloe the headshot he had taken but to his surprise he saw that the Green Arrow was in one frame and gone the next, leading Jimmy to believe that the Green Arrow was superhuman.
Season EightJimmy was close to discovering Clark's secret and Oliver asked to help him cover up his identity. Together Chloe, Clark and Oliver set up a plan to fool Jimmy into thinking that Clark wasn't the red blue blur. Oliver agreed with Clark that Jimmy was an innocent bystander and that his life did not need be complicated with the knowledge of Clark's secret. The plan was that Chloe would try to hit Clark with his car and Oliver, dressed in red and blue, would swoop in from a rooftop and save him, all in front of Jimmy. They coordinated the plan via cell phone as Clark and Jimmy walked down the street. Chloe set off to drive at Clark but he received a phone call from Lois and quickly walked across the road with Jimmy, leaving Chloe confused as she drove by. Clark told Jimmy he had to take care of something and sped off leaving Jimmy alone. A mugger working for Tess Mercer then grabbed Jimmy and forced him to walk as Oliver watched from the rooftop. Oliver swooped down using a grappling hook and saved Jimmy from the mugger just as Clark arrived back on the scene. Jimmy immediately thanked Clark for saving him, but Clark said it wasn't him and pointed at Oliver, who was standing tall on top of a building with a red cape blowing in the wind. Everyone in the street was looking in amazement, including Jimmy, at Oliver.
Oliver attended Chloe and Jimmy's wedding at the Kent Farm. Doomsday ended up crashing the wedding ripping Jimmy's chest open and kidnapping Chloe. Jimmy was said to be in critical condition at the hospital and was taken to a top surgeon in Star City, Oliver's hometown.Oliver was at the Ace of Clubs in the middle of a business deal when he was sought after by Jimmy who asked him for $600.00 in order to fix his car. Jimmy said he was "let go" from his job at the Ace of Clubs. When Oliver refused to give him the money as he believed Jimmy was going to use it to buy drugs and suggested he go to a rehab center. Jimmy became angry with Oliver and left. Oliver later found Jimmy breaking into Chloe's apartment, attempting to steal money from Chloe. Jimmy said it was just a loan and that he was going to pay Chloe back. Oliver then began to believe that Jimmy's car needed the repairs he was talking about. They were then both attacked by Davis Bloome and held captive in the Talon basement. When they both come to, Oliver wondered what had happened and Jimmy said Davis Bloome did this to them. They begin to wonder what had happened to Chloe and Davis came in and said he would never hurt Chloe. Davis warned Jimmy not to upset him and Oliver goes on to say gave a whole new term "Bridezilla". Jimmy concluded that Davis was the beast that attacked his and Chloe's wedding. Chloe then called and Davis told her a couple guys broke into her apartment and Oliver and Jimmy both yell to Chloe to stay. Chloe urged Davis to let them go but Davis said not until they leave Smallville and urged Chloe to hurry back before hanging up. Davis said to Jimmy and Oliver that if Chloe doesn't get back soon he would have to kill one of them. Jimmy began to taunt Davis into killing him but Oliver tried to cool Jimmy down. Jimmy yelled back that Davis had stolen his life and that now he nothing left to use. Davis grabbed Jimmy and his eyes turned red as he started to almost crush Jimmy's skull but Oliver said to him that Jimmy meant too much to Chloe and she would never forgive him for killing him. With that Davis knocked Jimmy unconscious and decided to kill Oliver instead. He grabbed Oliver's neck and began to choke him. Clark then intervened and saved them both and took Davis away. Oliver then contacted Dr. Emil Hamilton and had Jimmy taken to the hospital. Jimmy then later came to Oliver again at his office in the Luthorcorp building. Jimmy asked Oliver if he had a read on where Davis had went. Oliver went on to tell Jimmy that the beast he needs to be fighting is inside himself. Oliver gives Jimmy a check for the money to fix his car and offers him a job on his staff team. Jimmy was skeptical, but after Oliver complimented his courage for facing the monster and with having good instincts. With that Jimmy began to have hope and accepted Oliver's offer and check.
Oliver asked Jimmy to sneak into Tess's office at the Daily Planet and use a decryption key to decrypt her files on her computer. Jimmy proceeded to do so but stepped on Lois's toe who was hiding under the desk. Lois asked Jimmy who he was talking to and Jimmy replied nobody covering for Oliver. Jimmy decrypted Tess's computer and found Chloe and Davis's location in Edge City and gave the location to Oliver and his team. In the events following Davis and Doomsday were split by black kryptonite, Jimmy discovered Clark's secret, and Clark and Oliver's team buried Doomsday alive in the geothermal facility. Jimmy is then killed by Davis and Jimmy killed Davis protecting Chloe. Oliver attends Jimmy's funeral and is saddened as he shed a tear mourning the loss of his friend. He felt guilty that he caused Jimmy's death so after the funeral he left Metropolis.
Oliver still felt guilty over the loss of Jimmy. He headed down a dark path by getting into fight clubs and caused a high speed chase on his motorcycle. He even finally forced Clark to admit he was wrong about Davis and that he caused Jimmy's death.
- Oliver and Jimmy are the only two men Chloe have slept with. Both men also married Chloe.
- Both characters started off as recurring guest stars in Season 6 before eventually becoming main cast members.
- Oliver ended up replacing Jimmy in Chloe's life after his death.
|Oliver Queen in Smallville|