Evil Jeff is an alternate version of Jeff Winger, the product of a divergent timeline in which the study group suffered great personal losses. Jeff himself lost his right arm while trying to put out a fire. Devastated by those tragedies, the Abed of that reality dubbed this The Darkest Timeline, and suggested they become as dark and twisted as the reality they had to endure. Although Jeff at first refused, he had a change of heart and after freeing Evil Annie from the Greendale Insane Asylum, he now plots with the rest of the "Evil study group" to destroy the "Prime Timeline". His first appearance was in the Season Three episode "Remedial Chaos Theory". He is portrayed by Joel McHale.
In the study group's third year at Greendale, Troy and Abed decided to move in to 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 unfolded that split off from the "Prime Timeline" one which ended up becoming The Darkest Timeline. In that alternate reality, a chain of events led to Jeff having his arm amputated after it was severely damaged when he tried to put out a fire. The Abed of that timeline suggested an outrageous plan; they would all commit to becoming "evil" by wearing felt goatees, cross over to the "Prime Timeline" and take over their counterparts' lives. Jeff, having sunk into a bitter depression due to his loss, angrily refused Abed's suggestion stormed out of the study room ("Remedial Chaos Theory").
Jeff is in a state of shock after losing his arm.
However, sometime later he changed his mind and had come to embrace his dark side. After Evil Annie's criminal misdeeds landed her in the Greendale Insane Asylum, Jeff, acting as her defense attorney, went to court to fight for her freedom. He used his missing arm to play to the sympathy of the court due and argued Annie was too beautiful to lock away. He succeeded in securing her release and the two embraced in the courtroom. Annie asked him if he had a problem with the age difference now and replied he wished she was younger. Jeff then revealed he and the remaining study group were plotting to destroy the "Prime Timeline". The two laughed maniacally before they started kissing each other passionately ("Intro to Knots").
Evil Jeff and Evil Annie are reunited.
Eventually, Evil Jeff travelled to the Prime Timeline to corrupt it like Evil Abed had intended before he had a change of heart. He arrived along with Evil Annie on the day of his counterpart's graduation. Evil Jeff learned his doppleganger was offered a job at his ex-partner Mark's new law firm. He and Evil Annie decided to corrupt Jeff by forcing him to accept the job. To that end, they planned on turning the Study Group against him. Starting with Annie, Evil Jeff impersonated Jeff and visited each of his friends. He insulted them all causing them to refuse to show up their Jeff's his graduation ceremony. The only one not fooled by him was Abed who immediately identified him as "Evil Jeff". Using an advanced paintball weapon, he shot Abed which transported him to the Darkest Timeline.
Evil Jeff arrives.
Meanwhile at the graduation ceremony, Jeff is confused when the only one to show up was Evil Annie. She pretended to be his Annie and flirted with him while at the same time trying to get him to accept Mark's job offer. When her seduction failed she called in Evil Jeff. He tried to persuade Jeff to join the new law firm and return to his former life as a sleazy lawyer. When Jeff refused, Evil Jeff attempted to shoot him with his reality-warping paintball weapon he. Instead, he shot Ben Chang who valiantly sacrificed himself by intercepting the bullet. This allowed Jeff time to escape, angering his duplicate and Evil Annie. At that moment, the rest of the Evil Study Group appears, having crossed dimensions to provide assistance to the pair. After suiting up in matching leather apparel, Evil Jeff led his friends on a hunt to find each of their doubles.
Evil Jeff is armed and dangerous.
He was now intent on sending all of the "Prime Timeline" study group to his reality. They arrived in the cafeteria only to be surprised by the arrival of Evil Pierce. It turned out he faked his own death to teach them a lesson and followed them to the "Prime Timeline" to offer his help. However, he misunderstood what Evil Britta told him about the mission and shot himself with a paintball gun. Evil Britta accidentally shot herself as well, causing Evil Jeff to be exasperated at his cohort's stupidity. It's then that the "Prime Timeline" study group reveals they are inside the student lounge when Britta loudly takes exception to Evil Jeff berating her counterpart. The two groups face off and Annie, Shirley and Troy quickly dispatch their darker alternate selves.
Evil Jeff on the hunt.
Only Evil Jeff is left who lost track of his duplicate. Jeff then calls out to Evil Jeff who shoots a single paintball pellet his way. Jeff stands there unmoving as the paintball pellet races towards him and freezes it in place. Evil Jeff is puzzled at this turn of events as his counterpart shoots him with his own paintball gun sending him back to the Darkest Timeline. Afterwards, Evil Jeff and his Study Group have settled back into their lives in that reality. He interrupted Evil Troy and Formerly Evil Abed's morning show and expressed annoyance at their antics. He points out the fact that the show is fake and there isn't even an audience. Evil Jeff then tells them he'll see them later for lunch ("Advanced Introduction to Finality").
Evil Jeff being sent back to the Darkest Timeline.