We are officially a couple of months into the 2020–2021 school year now. As teachers are doubling down in a time when the format of teaching has potentially been forever altered in the face of COVID-19, we’ve expanded our celebration and support to their fictional counterparts.


What started as 22 competitors in Round 1 of our Back-to-School Showdown has been whittled down to six cutthroat challenges, all vying for the title of the most iconic pop-culture prof.


Will Mr. Keating seize the day, or will Dewey Finn stick it to the Man? Or maybe Deloris Van Cartier will come out on a high note. Vote below to pick the three greats who will move onto the finals in Round 4 — and may the best pedagogue win.


Sean Maguire vs. Mr. Keating

It was always going to come down to this: 1997 Robin Williams versus 1989 Robin Williams, in the gentlest of battles to determine who’s the most supportive classroom dad of all. Fans of tough love will likely opt for Dr. Sean Maguire, the psychology professor/therapist extraordinaire who mentors Matt Damon’s titular troubled genius in “Good Will Hunting.”


Will’s been through the ringer and has learned to hide his emotional scars all too well and it takes a guy like Sean, who won’t look down on Will but also won’t take his crap, to coax him out of his shell and help him start to heal. Sean is unafraid to cut to the heart of the matter and get personal when he needs to, and that makes him a great teacher…and it doesn’t hurt that he also knows how to rock the hell out of an argyle cardigan.