Jeff Winger and Pierce Hawthorne portrayed by Joel McHale and Chevy Chase.
Pierce and Jeff first meet at the study group's first study session where the elder member bungles the introductions for the rest of the attendees. The two settle into a slightly antagonistic relationship as Pierce obvious envy of Jeff causes friction between them. Jeff tries to tolerate his attitude but is annoyed by Pierce's contradictory attempts to obnoxiously insult him (usually questioning Jeff's sexual orientation) while also trying desperately to become his best friend. This dynamic has put a lot of strain on their relationship but on occasion the two will find some common ground. Pierce has shown to be a good sounding board and almost mentor for Jeff. Both see a bit of each other in themselves; Pierce sees the swagger he had when he was younger, Jeff sees who he might become when he is older if he's not careful. Jeff portrayed by Joel McHale, and Pierce is portrayed by Chevy Chase. Their first appearance together was in the Season One episode Pilot.
After forming a fake study group to impress Britta, Jeff is surprised when Abed invites a number of other students to join them. Pierce shows up and while trying to impress his new "tutor", messes up the introductions of the rest of the group. It's soon discovered Jeff was a fraud and he gets kicked out of the study session. Later, Pierce spots Jeff outside of the library and they have a brief conversation before being joined by the rest of the study group. Jeff is allowed to return to the group and over the semester Pierce tries to become his best friend.
"Interpretive Dance": Pierce tweets about the relationship between Jeff and Professor Michelle Slater. Jeff makes fun of Pierce's Twitter page in which he says he is 47 and teaches a women's only Pilates class.
Pierce and Jeff's second year together with the study group sees their relationship becoming more strained. Throughout the year he feels disrespected by the study group and Jeff starts excluding Pierce deliberately from other group activities which results in a growing animosity between the two. While at the hospital dealing with a drug overdose, he fakes that he is on his death bed and bequeaths items to the study group to mess with their minds. Later, the two take a Wine Tasting course together and Jeff is shocked when he is rejected by a beautiful classmate named Wu Mei and Pierce successfully woos and becomes engaged to her. Sometime near the end of the year, the study group at Jeff's behest holds a secret meeting to determine whether or not Pierce would be allowed to return to the group for the next semester. This comes to light during the 2011 Paintball Assassin game. At Pierce's hideout, the study group confronted Pierce after he betrayed Jeff by giving him a paintball pistol full of blanks. Pierce and Annie had a one on one paintball pistol duel over the matter. Pierce faked a heart attack, eliminated the Black Rider and retreated during the chaos declaring that he's quit the study group. After the game escalated into a full on war between the remaining Greendale students and the invading City College Storm Troopers led by Dean Spreck, Pierce surprisingly wins the competition and the prize money of $100,000. Although he generously gives the money to Greendale for repairs he adamantly refuses to return to the study group even after Jeff tries to welcome him back.
"Asian Population Studies": Pierce opposes Jeff who wants Chang to join the study group. Pierce wants to have Rich (and his kettle corn) join. After Jeff wins, Pierce says Jeff has hurt the study group in a way that will never heal.
"A Fistful of Paintballs": In a flashback to events prior to the paintball competition it's shown that Jeff and the study group voted on whether or not Pierce would be allowed to return to the group the next semester.
"For A Few Paintballs More": Pierce emerges the victor of the paintball war winning the prize money for Greendale. Jeff and the rest of the study group offer to forgive his previous actions and let him back into the group but he refuses saying he is done with them.
Pierce returns to the study group angering Jeff who believes his absence will make the third year at Greendale much better. After Jeff is ejected from the Biology class the group is taking he ends up being split off from the group. After accidentally inhaling monkey gas, Jeff goes crazy and attacks the study table. Pierce decides to cover for his behavior explaining to Jeff that he seemed to be having a harder time dealing with being excluded from the group. The two make peace and settle into a less antagonistic dynamic. Jeff decides to force Pierce to deal with his overbearing father Cornelius Hawthorne and later confronts the elder Hawthorne ostensibly on Pierce's behalf although it's clear he is working out his own daddy issues. Towards the end of the semester, Jeff and the study group help Pierce win his inheritance by playing a video game. Along with the rest of the group they are expelled for causing a riot in the cafeteria during Star-Burns wake. Together they help to overthrow Chang's regime at Greendale by taking part in an elaborate heist. During the summer time, Jeff finds himself in Greendale court representing Shirley in a case against Pierce with his attorney Alan. The conflict arose due to a business contract Shirley and Pierce were offered by Greendale for Shirley's Sandwiches shop which only required one of their signatures. A patented Winger speech resolved the situation and Jeff was named as Pierce and Shirley's representative and authorized to sign the document in their names.
"Biology 101": Pierce returns to the group just as Jeff becomes excluded from it.
"Competitive Ecology": When Jeff objects to being paired with Todd and accuses someone in the group of ranking him last, Pierce calls him a pompous ass.
"Advanced Gay": Jeff confronts Cornelius Hawthorne on Pierce's behalf and accidentally causes his death. Pierce later hands Jeff his father's ivory toupee as Cornelius' will stated whoever killed him would receive it.
I can't believe I'm about to say this. The only reason he can be unpleasant is because we expect him to be. If we don't treat him like such a dick, well he'll probably still be one 98% of the time, but the 2% he's tolerable it might be worth it.
Pierce and Jeff's fourth year together along with the study group sees them failing to get into the History of Ice Cream class and having to take a history course with Professor Cornwallis. During Halloween, Pierce calls the Jeff and the study group to rescue him as he trapped himself inside his mansions panic room. Pierce later invites Jeff to join him at his barber shop for a shave. Although he was only there to distract Pierce from a rich student that was being pursued by Greendale, Jeff finds himself enjoying the time he spent there with Pierce. When Britta follows through on a mistake for a dance by naming it after Sophie B. Hawkins and then having to try and book her, Jeff makes fun of her "Britta'ing" it. Pierce gets Hawkins to appear and scolds Jeff for treating Britta meanly. As Jeff is about to graduate at a special ceremony for him, Pierce interrupts and says he is going to graduate first. Jeff defers to Pierce and applauds.
Jeff returns to Greendale in 2014 as a lawyer intent on using his old study group to launch a class action suit against Greendale. He is successful and is about to go file the suit when he runs into a hologram of Pierce (who has been banned from Greendale for sexual harassment) outside Borchert Hall. What the hologram says changes Jeff's mind on filing the suit and he decides to quit the law and become a teacher at Greendale. Pierce's hologram delivers the following speech:
"Continue on this path, and you might miss your last chance to see the Pierce Hawthorne Museum of Gender Sensitivity and Sexual Potency on the central quad.
The museum and this hologram were donated in compliance with a court order I'm not allowed to discuss. Let's just say some women can't take a compliment.
What I am allowed to discuss is Greendale, and I'll say this Don't turn your back on it. Take it from a man with no legal right to be there. You're in a special place. A crappy place, sure, but only because it gives crappy people a chance to sort themselves out. Did I sound gay at the end? Do you want to do another take?"