1) Steve Martin (as a stand-up)They rocked high school in every way imaginable: valedictorian, a 4.5 GPA, president of every club, star of every team. That all changed when they got to college (on a full scholarship, no less) and decided they just didn't care anymore. Their grades are awful, they have no ambition, they picked a throwaway major, and generally don't care about anything past television and getting Twitter followers. They've also picked up weird hobbies like the banjo.
2) Chevy ChaseEverything came easy to them in high school. They weren't the smartest or the most talented but got by on their looks, charming their teachers into good grades while getting away with murder. They tied for multiple Senior Superlatives, most notably "Best Hair" and "Most Likely to Succeed". Now that they've left their hometown, no one cares how cool they were in high school and they can't stand it. Their reputation didn't follow them and professors don't care how charming they are so they're failing. People can't stand their arrogance and they're getting fat. They go home a lot to relive the glory days but even their old friends are sick of their routine and are moving on without them.
3) Will FerrellPopular, good student, really involved and ambitious, all that seems to have been thrown out the window the day they met their assigned roommates. They hit it off immediately, but now all they want to do is smoke and play video games with them. They're failing classes because they don't take school serious but if you have a conversation with them you find out they're actually a genius: very well read, quick witted, very thoughtful and deep. They'll explain why you missed that Organic Chemistry question better than your professor while packing another bowl. They could do anything they wanted to if they just got away from their loser friends, but they don't care what anyone thinks about them, valuing their friends more than being successful.
4) Louis CK This kid flew under the radar in high school, making average grades and not straying outside their small but close group of friends, known as "oh ya, that guy" to most people. They cracked jokes but they always fell flat on their classmates, either being too intelligent or too mature for high school audiences. They didn't really party or care about the football team, adding to their troubles fitting in. Then they had a growth spurt/lost their braces/their acne cleared up and they are looking good for the first time in their life. They've reinvented themselves in college and are finding real social success as a result: they get invited to things, they've found people who get their sense of humor, and they found a major that plays to their strengths so they're making the best grades they've ever had.
5) Chris FarleyThey were an instant hit they second they set foot on campus. Funny, lovable, charming, the life of the party, everyone wants to be where they are. Their appearance can make or break a party. People know they have a drinking problem and wonder if they've ever attended a single class but don't want to interrupt the show so they let them go down the path of destruction. They eventually flunk out and have to move home, never to be heard from again.