|Portrayed by Richard Erdman as Leonard, Alfred Dennis as Richard, Lee Weaver as Joe, and Edith Jefferson as Pearl|
|First seen||"Messianic Myths and Ancient Peoples"|
|Meeting area...||Storage room|
|At Greendale to...||...be old and crotchety|
|Members||Leonard, Joe, Richard, and Pearl with Pierce as an "honorary" member|
|“||You're his worst nightmare now, you're old and you don't give a damn!||”|
Greendale Community College is known for having a diverse student body. A few of the students more advanced in age banded together united by their defiant nature, contempt for the young, and the need to disregard all the rules. Led by Leonard, they were a thorn at the side of Dean Pelton and an inspiration to Pierce who admired their attitude. Their first and only appearance together was in the Season Two episode "Messianic Myths and Ancient Peoples". They are portrayed by Richard Erdman as Leonard, Alfred Dennis as Richard, Lee Weaver as Joe, and Edith Jefferson as Pearl.
In the study group's second year at Greendale, Pierce began to feel alienated from the other members because of the age difference. In the cafeteria Pierce runs into Leonard and meets kindred spirits in his circle of friends Richard, Joe and Pearl. Britta tries to coax Pierce back to the study group but the Hipsters chase her off with insults and Pierce sits down at their table instead. Later, in a storage room, Pierce joins Leonard and his friends as they smoke cigars, drink alcohol and play a game of poker. Dean Pelton interrupts the carousing and tries to break it up but Pierce fakes dementia earning his sympathy and getting him to allow them to continue. While his actions won Pierce the approval of Leonard's group, it later causes problems with the study group who are worried about his association with "The Hipsters" and the effect it's having on his attitude. Pierce ignores their concern and abruptly leaves the study session to meet up with his new friends joining them outside the library. As they are loitering and imbibing more alcohol, Dean Pelton and Shirley drive up to the buildings entrance in his car. The pair are accosted and taunted by the elder students as they enter the building. Leonard then discovers that Pelton left his keys in the car and proposes they all go for a joyride. He lets Richard take the wheel as Leonard assures a worried Pierce that they are safe with him driving as he is a War World II vet who flew planes in the war. Unfortunately, Richard then experiences actual dementia and loses control of the car unable to remember who he is or what he is doing. The car very slowly hits a light pole which causes the other Hipsters to flee the "crime scene" leaving Richard and Pierce behind who opted to stay with the confused driver. The Hipsters and Pierce are rounded up by campus security and taken to Dean Pelton's office where they are held until they can be picked up by their family. Jeff, Pierce's contact, is greatly annoyed when he shows up to "bail" Pierce out. However, Jeff softens when he learns that Leonard's family has long since stopped responding when Leonard pulls such stunts. When Pierce is released he tries to explain that what happened wasn't his fault but Jeff refuses to listen and tells him to go wait in his car. In defiance, Pierce knocks a pile of papers off of the office counter and storms off as Leonard and his friends cheer him on.