In the study group's first year at Greendale, Jeff becomes frustrated by the shortage of Chicken Fingers in the cafeteria. He and the rest of the group had Abed placed in the position of fry cook at the cafeteria to insure they would always have chicken fingers. Abed takes this one step further by creating a Chicken Finger mafia and culling favors from the student body, and even the faculty, for their share of the popular food item. Abed spreads the wealth by awarding gifts to the study group members for their services. A monkey was given to Troy who named him "Annie's Boobs" after a contest on his pet monkey's Twitter account, much to Annie's annoyance. It was later released from its cage by Abed after he felt disrespected by his friends despite his best attempts to make them happy.
"Contemporary American Poultry": After forming the "Greendale Chicken Finger Association", Abed gives out boons to the study group. Among the various gifts Abed gives Troy a pet monkey that he names "Annie's Boobs"
In the group's second year at Greendale, Annie's Boobs returned stealthily stealing a pen and resulting in an inquisition led by Annie to discover who stole her property ("Cooperative Calligraphy"). The monkey had apparently been collecting various items related to the study group. He kept his growing collection inside his home in the school's air vents. It wasn't until the end of the year that the group learned he was responsible after Troy noticed him stealing a paintbrush he was using for the group's latest diorama project for Anthropology. Ben Chang followed the monkey into an air vent, finding all the stolen loot he had accumulated over the last year. When the group members see the recovered items they begin to reminisce about recent adventures they had together. For his part, Chang remembered all the times he and the monkey shared which was Annie's Boobs hitting him repeatedly ("Paradigms of Human Memory").
"Paradigms of Human Memory": The study group learns the monkey stole Annie's pens and after looking over the rest of it's hoarded items they start to remember various events from the past year.
I will not tolerate monkey's living on campus. If I wanted to run a monkey hotel, I'd install a banana buffet. I'd use vines as elevators, I'd put tail holes through the bathrobes and I'd lower the shower knobs.
In the study group's junior year at school, Dean Pelton instituted a zero tolerance policy on monkeys at school. He charged the head of Greendale security, Sgt. Nunez, to capture Annie's Boobs, who was hiding in the air vents. Nunez and his staff decided to pump the monkey gas Chimpan-Zzz's into the air vents in hopes of flushing out the animal. It was unsuccessful and they ended up accidentally hitting Jeff and Ben Chang with the gas instead. After winter break, Shirley had a quick engagement to her ex-husband Andre Bennett and decided to hold the wedding in the study room. At the wedding reception also held in the study room, the monkey sneaked out of his home in the air vents to look in on the festivities. Troy noticed the monkey, which shook him out of a forced "normal" persona. He had created this new identity after an all night Dreamatorium session with Abed just before the wedding. Seeing the monkey helped to reawaken Troy's whimsical side and he quickly went to Abed and helped him to shake his "normal" persona as well ("Urban Matrimony and the Sandwich Arts").
In the study group's senior year, Abed is in therapy with Britta who suggests that whenever he feels anxiety he should retreat to a "Happy Place" inside his mind. It's shown that this place is an exaggerated sitcom version of his life. Annie's Boobs appears as part of Abed's "Happy place" interacting with Annie ("History 101"). Towards the end of the semester, Abed later discovered that Britta and the monkey had met much earlier after studying the interconnected history of the study group. In a flashback to the year 2008, it's revealed that Annie's Boobs was a test animal and a scientific research lab. At that time Britta was an activist who had been trying to make a name for herself after her anarchist group recently disbanded. She broke into the lab and freed the monkey but was unable to control it. Britta who ran out of the lab screaming while continuing to struggle with the monkey. ("Heroic Origins").
"History 101": Abed imagines a sitcom fantasy version of his life when he retreats into his inner "Happy Place" after struggling to accept that this may be the study group's last year together. He imagines that Annie's Boobs is in that reality interacting with Annie.
"Heroic Origins": It's revealed that Britta freed the monkey from the animal test lab back in 2008 during her anarchist phase. Abed shows another unknown previous connection on his chart by showing Cornelius Hawthorne, Pierce's father, was the owner of that scientific research lab.