Essays on teaching comedy in literature, writing, theater, and cultural studies courses. From Shakespeare to The Simpsons, comedy has long provided both entertainment and social commentary. It may critique cultural values, undermine authority, satirize sacred beliefs, and make room for the marginalized to approach the center. Comedy can be challenging to teach, but in the classroom it can help students connect with one another, develop critical thinking skills, and engage with important issues. The essays in this volume address a rich variety of texts spanning film, television, stand-up, cartoons, and memes as well as conventional literary works from different places and times. Contributors offer theoretical foundations and practical methods for a broad range of courses, including guidance on contextualizing the humor of historical works and navigating the ways that comedy can both subvert and reinforce stereotypes. Finally, the volume argues for the value of comedy in difficult times, as a way to create community and meaning. This volume contains discussion of fiction, poetry, plays, and essays by Maya Angelou, Jane Austen, Aphra Behn, Hugh Henry Brackenridge, Frances Burney, Charles W. Chesnutt, Roddy Doyle, Maria Edgeworth, Ben Jonson, Anita Loos, Emtithal Mahmoud, Thomas Middleton, Okot p'Bitek, William Shakespeare, Laurence Sterne, Jonathan Swift, Alma Villanueva, Paula Vogel, Oscar Wilde, John Wilmot, and William Wycherley; TV shows and films including Crazy Ex-Girlfriend, The Gold Rush, Life Is Beautiful, The Marvelous Mrs. Maisel, The Office, Office Space, Rick and Morty, and South Park; works and stand-up performances by Aziz Ansari, Samantha Bee, Dave Chappelle, Louis C.K., Tina Fey, Moms Mabley, Hasan Minhaj, Eddie Murphy, Trevor Noah, Richard Pryor, Issa Rae, and Wanda Sykes; and visual works and other media including Aaron McGruder's The Boondocks, Bill Watterson's Calvin and Hobbes, Nick Sousanis's Unflattening, Marvel's Hawkeye, The Onion, YouTube videos, advertisements, and memes.