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Jeff and Ian’s relationship is an off-again on-again friendship.

Jeff Winger[]

Jeffrey Tobias "Jeff" Winger (played by Joel McHale) is a graduate of Greendale Community College and currently a Professor of Law at the school. He was born in Denver, Colorado to his parents William Winger and Doreen Winger née Fitzgerald. His father divorced his mother in 1983 when he was very young and would go on to have another child named Willy Junior. As an adult, Jeff became a very successful defence attorney specializing in DUI/DWAI/DUID cases, traffic offences, and juvenile crimes for over six years. He worked for a law firm called Hamish, Hamish & Hamlin that was founded by Ted. At work, he was often partnered with another lawyer named Markand the two were known as "Tango & Cash" respectively. A drunk driving case Jeff handled involved a Psychology Professor named Ian Duncan with whom he became good friends. At the height of his success at the firm, Jeff's fraudulent academic credentials were exposed by a colleague of his named Alan Conner. Jeff was disbarred with his license suspended until he earned a legitimate degree. For four years he went to Greendale Community College with this goal in mind. During this time, he became close friends with a study group he formed. After having earned an Associate's degree in Education, he briefly returned to practicing law and started his own law firm. It was unsuccessful and he returned to Greendale where he accepted an offer to teach Law. He was also reunited with his study group and joined a special "Save Greendale Committee" to improve campus life.

Ian Duncan[]

Dr. Ian Duncan(portrayed by actor/comedian John Oliver) is a psychology professor at Greendale Community College. Ian was born in Birmingham, England and grew up on 52nd street in the Islington district of London (although this is actually a writing error as confirmed by Dan Harmon, as British streets are not numbered). His mother was a native of Lincolnshire, from a town called Scunthorpe where she worked as a whore at a Stansbury pub with her thumb-less sister. Duncan's father was absent for much of his childhood and it's alluded that he left England shortly after his parents divorced. He came to America with his grandfather when he was very young and eventually became a psychologist. He was hired by Greendale Community College and was made the head of its psychology department. Duncan started drinking heavily and his addiction caused him to run into some legal problems. At one point during driving drunk, he tried to order chalupas from an emergency call box on a highway. Jeff Wingerwas still a practicing attorney at the time and managed to get Ian off the hook. The two became drinking buddies, and, years later when Jeff enrolled at Greendale, he unsuccessfully tried to call upon the favor Ian owed him. Although Duncan was present during Jeff's first and second year at school, he took a leave of absence before his friend graduated. He spent that time back in England taking care of his mother who was ill. Duncan returned to his position at Greendale a few years later and reconnected with Jeff, who had since become a member of the faculty.

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