|Pierce and Annie|
|Portrayed by Chevy Chase and Alison Brie|
|“||Come on Annie, I don't want to beat you. You're my favorite!||”|
Of all the study group members, Annie is the most tolerant and patient when it comes to Pierce. Pierce is often nicer to Annie than he is to anyone else in the group, he appreciates her kindness and tries to reciprocate it. However, he still manages to unintentionally offend her at times with his racist viewpoints and churlish behavior. Despite this, Annie will most often come to Pierce's defense whenever he offends the group. It's because she is unwilling to break up the close circle of friends they have which she considers her family. A few times she had to side with the group when he went to far. A falling out towards the end of their sophomore year together at Greendale resulted in Pierce leaving the study group. However, Annie is genuinely pleased when Pierce decides to return to the group in the following semester. Pierce is portrayed by Chevy Chase and Annie is portrayed Alison Brie. Their first appearance was in the Season One episode Pilot.
|“||You listen up, Pierce! I'm gonna tell you what my mother told me when I wanted to quit cheerleading. 'You're not very pretty, you have no boobs, and you can't do a basket toss to save your life.' But you made a commitment. So pick up your pompoms, Pierce, stuff your bra, and get ready for the team bus to forget you at a Taco Bell, because life is tough. But we soldier on, and that's just the way it goes.||”|
–Annie, "Advanced Criminal Law"
Pierce offers to help write the new school anthem for Annie when she is the chairperson for the committee to come up with the new school song. Annie helps him when he has writer's block and he made a dedication to her in a song that he "wrote". At Annie's "Dias De Los Muertos Party" Pierce, while under the hallucinogenic influence of Star-Burns drugs, gives Annie a creepy back massage. During the school's Valentines Day week celebration, Pierce and Troy are humiliated by Ben Chang and Annie and Shirley team up to get revenge for their friends. At the end of the school year, Pierce and the rest of the study group say their goodbyes to Annie who was leaving for the summer to go with her boyfriend Vaughn to Delaware. He tries to hug her but she instead shakes his hand.