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 too 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.
Pierce offers to help write the new school song 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 "Dia 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.
At the start of the 2010 fall semester at Greendale, Pierce and Annie reunite with the other study group members in the study room. Messy relationship problems Annie and Pierce had with other people nearly tears apart the study group. Afterwards, Annie notices that Pierce is acting out and hanging out with a group of elderly students who are a bad influence on him. On Halloween, Pierce gets sick during a party Dean Pelton is throwing. Annie, along with Dr. Rich Stephenson, discover that the taco meat served at the festivities has caused a viral outbreak with Pierce being the latest victim. Pierce's misfortune continues when he breaks both legs using a trampoline and ends up in a wheelchair for a time. When the group searches for Annie's pen, things get heated as accusations start flying concerning who is to blame. Pierce attempts to join in when things spiral out of control after Jeff and Annie start stripping in a convoluted attempt to prove their innocence. On Christmas, Annie, Pierce and the rest of the group participate in a therapy session with Abed. Later, Annie stages an anti-drug play for middle schoolers with Pierce and the study group. When Pierce provides rent money for Annie's apartment, he guilts her into letting him have a bigger part in the play. Afterwards, Annie becomes concerned that Pierce is addicted to his pain medication for his recent injury and tries to get the group to stage an intervention. When Pierce overdoses, he uses his hospital stay as an opportunity to play a prank on the group. He pretends he is dying and hands out bequeathals. Annie receives a diamond tiara, but she returns it, believing it to be Pierce's way of testing her resolve. He privately admits there were no strings attached to the gift and that he gave her the tiara because she is his favorite in the group.
"Anthropology 101": Fallout from Pierce discovering the Twitter account Troy set up to mock him and Annie's revelation that she kissed Jeff the night of the Tranny dance nearly splits the study group apart.
"Epidemiology": Annie is concerned when Pierce exhibits odd behavior after eating "taco meat" at the Halloween party.
Annie welcomes Pierce back enthusiastically when he unexpectedly returns to the Study Group. Along with their friends they enroll in a Biology class taught by Marshall Kane. At the start of the year Annie is warned by Pierce about a student she met named Annie Kim. He and the rest of the group help Annie in her rivalry with Kim by participating in a team model U.N. showdown. They both attend Troy and Abed's house warming party in their new apartment where they avoided a dark scenario. Annie is proud of Pierce when he decides to market his Hawthorne Wipes product to the gay community. She later supports Pierce by attending his father's funeral. While helping Annie move into Troy and Abed's new home, Pierce accidentally damages Annie's old apartment. Before the Winter Holidays start, Annie and Pierce join the school's Glee Club and help recruit the rest of the study group. After they returned, Pierce started a business partnership with Shirley before she got re-married to Andre in a ceremony Annie helped put together. Pierce and Annie volunteered to perform at a birthday party to clear a debt Abed had with a local business. When Troy and Abed have a falling out Annie and Pierce got sucked into the drama as did the rest of the campus. Not long afterwards the study group is expelled after they helped instigate a cafeteria riot at Star-Burns memorial. During their absence from school, Annie and their friends help Pierce with an unusual stipulation in his father's will. A caper is then planned for them to return to Greendale and overthrow Chang who took control of the school. Pierce and Annie played key roles in the operation and Chang was successfully ousted. Pierce, Annie and the others take summer classes to make up for their lost credit. Pierce and Shirley are unexpectedly given an opportunity to start a sandwich shop at Greendale but argue over who should be credited as the owner. After this is resolved Annie assists Pierce and Shirley in debuting their new sandwich shop in the cafeteria.
"Biology 101": When Pierce unexpectedly returns for the third year with the Study Group, Annie greets him enthusiastically and asks him how his summer was. She is also excited when Pierce joins them in Biology 101 class.
"Geography of Global Conflict": Pierce and the study group join Annie's Model UN team. Pierce represents Somalia and constantly paints it as a paradise.
"Advanced Gay": When Pierce sees Urbana Champaign's video and says he's going to sue the pants off that lady, Annie corrects him and says it isn't a lady. When Pierce introduces his father to the group, Annie says that she thought he was dead.
"Studies in Modern Movement": When the group (minus Jeff) help Annie move, Pierce offers to fix a broken outlet. He ends up damaging the wall, trying to paint it and being overcome by paint fumes. After the landlord saves him, he tries to kiss Annie.
"Regional Holiday Music": When Troy and Abed appeal to Pierce's vanity to rope him into joining the Glee Club's Christmas Pageant, Annie tells him to resist.
"Origins of Vampire Mythology": After Chang stops being Pierce's new BFF, Pierce goes to Annie, Troy and Abed's apartment and asks Annie to take his phone and to stop him if he tries to contact Chang.
In the Study Group's senior year at Greendale, Pierce asks for their help on Halloween unlocking him from the panic room in his mansion. He actually intends to prank them for not taking him to a Halloween party hosted by Vicki. In one prank, Pierce dresses as his dead father and scares Annie through a mirror. When The Germans want to use part of the study room for a day, Annie says they should allow it which Pierce disagrees with and he insults Annie. Pierce, Annie, Troy and Abed spend Thanksgiving at Shirley's house. They find her relatives hard to deal with and want to leave. Annie fakes menstrual cramps but Shirley's sister in law is a gynaecologist. Pierce crashes into furniture but evokes so many laughs he decides to stay.
"History 101": Annie, Pierce and the Study Group help Abed cope with his anxiety over this being their last year together at Greendale since Jeff is graduating early.
"Paranormal Parentage": At Pierce's mansion on Halloween, he pranks Annie by appearing in a mirror dressed as his dead father.
"Alternative History of the German Invasion": Pierce insults Annie for her wanting to let the Germans use part of the study room for a day. Later, he and Annie help clean up another study room by removing a dead raccoon from an air vent.
"Cooperative Escapism in Familial Relations": Pierce, Annie, Troy and Abed spend Thanksgiving at Shirley's house. They find her relatives hard to deal with and want to leave. Annie fakes menstrual cramps but Shirley's sister in law is a gynaecologist. Pierce crashes into furniture but evokes so many laughs he decides to stay.
"Intro to Felt Surrogacy": The Study Group takes a balloon trip and ends up stranded in the woods. They reveal their most terrible secret. Annie admits she let Professor Noel Cornwallis rub her feet for answers to a test. Pierce admits he never slept with Eartha Kitt.
“You know, you and I are very much alike, Annie. We're both realists. We're both cute. And we'd both rather die than let someone else control us. I see the point of this place now. This crap hole is a monument to self-reliance.”— Pierce