Injecting political commentary into comedy is nothing new, but with the increasing surreality of the American government, it seems more prevalent than ever. What’s the best way to approach tackling politics in comedy—and at what point does it become too heavy-handed? We asked Bob Odenkirk, Keegan-Michael Key, Jason Sudeikis, and more to weigh in while they were in Chicago for Second City’s Roast Of George Wendt.