Throughout his time on Community, Jeff Winger has been no stranger to dirty deeds, but one of Jeff’s actions takes the cake for the worst thing the former lawyer has done. Jeff Winger (played by Joel McHale) was introduced to the world as a fast-talking, charismatic bad boy who is willing to stoop to any low to get what he wants. Jeff’s lack of decency was even on full display in the pilot episode, as his formation of the iconic study group was merely a ploy to get with classmate Britta Perry (Gillian Jacobs). Even though Jeff has had one of the more remarkable character arcs on Community, he has also had some less than remarkable moments along the way.
Jeff Winger graced Greendale Community College as a recently disbarred attorney who must now earn a college degree after faking his lawyer credentials. From the very first episode, Jeff made it clear that he has no intention of coming to Greendale to earn an honest education. Often times, he just ends up using his fellow study group . From faking a class for a free credit to creating degrading nicknames for his classmates, there is no short list of terrible conduct for Jeff Winger.
The worst thing Jeff Winger did was maintain his creepy and inappropriate relationship with Annie Edison (played by Alison Brie). Even though Britta was Jeff’s love interest during Community's first two seasons—especially throughout season 1—Jeff found himself having feelings for his significantly younger classmate as the series dragged on. Despite the fact that their relationship never matured into a full-fledged romantic entanglement, Jeff's actions lead one to believe that it's all just talk. In fact, Jeff wants to be more than just friends.
How Jeff Winger Changed By The End Of Community
Jeff finishes Community as someone who is willing to put other people's needs before his own—something that Jeff would never even dream of doing in season 1. During Community's season 6 finale, Jeff begins to live an honest life by embracing his fears of abandonment and choosing to open up to his friends. Jeff lets go of his fantasies for Annie and begins the process of being there for those he loves.
There are plenty of moments throughout Community's 6 season run that s the claim that Jeff isn't the best person. Nevertheless, by the show's conclusion, Jeff finds himself to be a different character. Even though Jeff still holds many of his same fears and insecurities, including his love and desires for Annie, he also manages to find redemption for the worst thing he's ever done.