Evil Annie is an alternate version of Annie Edison, the product of a divergent timeline in which the study group suffered great personal losses. Annie was consumed with guilt over her part in the death of that world's Pierce Hawthorne. Devastated by those tragedies, the Abed of that world dubbed this "The Darkest Timeline", and suggested they become as dark and twisted as the reality they had to endure. Annie herself had became corrupted, committing crimes which led to her being locked up in the Greendale Insane Asylum. Evil Jeff freed her and plotted with the rest of the "Evil Study Group" to destroy their duplicates in the "Prime Timeline". Her first appearance was in the Season Three episode "Remedial Chaos Theory". She was portrayed by Alison Brie.
In the study group's third year at Greendale, Troy and Abed decided to move into an apartment together. A housewarming party was thrown where a the roll of a Yahtzee die determined who would go downstairs to grab the pizza from the delivery guy. Six different scenarios were unfolded split off from the "Prime Timeline" and a dark timeline was created. In that alternate reality, a chain of events led to Annie's gun accidentally being discharged and shooting Pierce in the leg. The group believed he died from his wound, which caused Annie to become mentally unbalanced from the guilt ("Remedial Chaos Theory"). She was committed to a psychiatric institution to deal with her issues, but it proved unsuccessful. It's later shown that she was eventually released, but had changed for the worse due to her experiences.
Now "evil", the Darkest Timeline version of Annie went on to rob a number of pharmacies, stabbing a few people in the process. This landed her in the Greendale Insane Asylum for her misdeeds. She was deemed so unstable she had to wear a restraining mask and straitjacket to prevent her from hurting others. Eventually, the Jeff Winger of that timeline, now having embraced his own evil side, went to court to fight for her freedom. Playing on the sympathy of the court due to his missing arm and arguing Annie was too beautiful to lock away, he succeeded in securing her release. After she was freed, the two embraced and she asked him if he had a problem with the age difference now. He replied he wished she was younger and then revealed he and the remaining study group were plotting to destroy the "Prime Timeline". The two laughed maniacally before kissing each other passionately ("Intro to Knots").
Evil Jeff and Evil Annie are reunited.
Upon arriving in the "Prime Timeline" Evil Jeff learns from Britta that Jeff is about to officially graduate. He is also hesitant to accept a job offer from his former colleague Mark, who had started up a new law firm. After Britta left, Evil Jeff determined that Jeff's friendship with the study group is clouding his judgement. It's then that Evil Annie shows up with Evil Jeff's artificial arm so he could masquerade as his double. He explained Jeff's fear of relapsing into his old selfish ways after graduating. The pair decided to sabotage his relationship with the study group in order to force Jeff to accept Mark's job offer. The first victim they targeted was Evil Annie's counterpart. Evil Jeff cruelly flirted with and then rejected "Prime Timeline" Annie. In the cafeteria, Evil Annie observed her counterpart confronting "Prime Timeline" Jeff for his actions.
Evil Annie brings Evil Jeff his Evil arm.
Evil Annie then posed as her double when The "Prime Timeline"'s Jeff looked for his Annie in the library. Evil Annie explained Annie's actions in the cafeteria was just her having anxieties about Jeff leaving Greendale. While hugging out an apology to Jeff, Evil Annie managed to grab his cell phone. She later showed up to Jeff's graduation ceremony just as an angry Dean Pelton was leaving the study room in tears. He had just confronted Jeff over things Evil Jeff had actually said to him. While Jeff struggled to figure out what that was so about he became even more confused by "Annie"'s behavior. She told him not to worry about Pelton or the others showing up for his ceremony. She then revealed a tight red dress she was wearing and began flirting with him. Evil Annie handed Jeff his phone back and suggested he call Mark to accept the job offer.
Evil Annie flirts with "lame" Jeff.
Jeff tried to exit the study room, put off by her aggressiveness and the absence of the study group. Evil Annie called out to her partner and Evil Jeff (Jeff's "Darkest Timeline" counterpart) stepped in to prevent him from leaving. Evil Jeff insisted he take the job, leave his friends behind and reclaim his former selfish lifestyle. Jeff refused, insisting he changed and was no longer that guy. He emphasized his choice by tearing up his diploma eliciting a sarcastic response from Evil Annie on how melodramatic he was being. Evil Jeff then decided to use his special paintball gun and send him to the "Darkest Timeline". At that moment, Ben Chang stepped into the study room and jumped in the way, taking the paintball pellet meant for Jeff, who escaped. Evil Annie asked what their next move should be just as the rest of the Evil Study Group arrived to offer their assistance.
The rest of the Evil Study Group arrives.
After Evil Annie and Evil Jeff suited up, they decided to hunt down their counterparts. They searched the cafeteria but instead were shocked to find Evil Pierce, whom they believed to be dead. He told them he faked his demise to teach them all a lesson (which he couldn't remember) and expressed his annoyance that he was left out of the timeline invasion. Evil Annie reminded him that they believed he was dead, but he insisted he could help them out. He then misinterpreted Evil Britta's explanation that the first one to shoot themselves would win. Pierce shot himself with his paintball gun, as did Evil Britta, unintentionally. The two were sent back to their reality as an exasperated Evil Jeff mocked them both.
The Evil Study Group learn Evil Pierce is alive.
Reacting to the evil version of Jeff's harsh words toward her own duplicate, Britta accidentally revealed she and the "Prime Timeline" study group were there. The two groups scattered with each member facing off against their counterpart. Evil Annie found her double hiding in the "Shirley's Sandwiches" shop. She started taunting her duplicate by saying that she should allow herself to be shot and sent to the "Darkest Timeline" since Jeff is sleeping with her in that reality. Annie revealed her location, intrigued by the thought, as Evil Annie elaborated by saying they had sex all the time and that he loved it. Angered at her response, Annie jumped over the countertop and shot Evil Annie with her paintball gun, sending her back to her own timeline. Annie then stated: "Nobody sleeps with Jeff...not even me." ("Advanced Introduction to Finality").