By 2017, The Simpsons creators had amassed 28 seasons, nearly 600 hand drawn episodes that each take 6 months to complete, and hundreds of characters with catchphrases that have stood the test of time. Put quite simply, The Simpsons changed the television game in so, so many ways. It’s currently the longest running sitcom in U.S. history, and so woven into the tapestry of American storytelling that it’s even become infamous for predicting some key cultural and political events (like, for instance, the Trump Presidency). Sometimes we may not even see its full ripple effect. Did you know, for example, that “D’oh” made it all the way into Webster’s dictionary?

While reinventing prime time television, The Simpsons also paved the way for animation to take its place as a genre with the unique ability to present some pretty dark social commentary while still remaining fun through the magical surreality of its cast of characters. The show has something for everyone: there are plenty of silly jokes that induce gut-busting laughs across generations, as well as some of the most genius execution of satire that television has seen yet. Despite its history of brilliantly lampooning every taboo (religion, race, sexuality, politics, and more), The Simpsons never loses sight of its heart: the stories that surround the shows expansive assortment of well-loved characters.

Whether they drew you in for just one episode or grace your TV courtesy of reruns every night of the week, each Simpsons fan has a character that speaks to them. And though it pained me deeply, I curated a list of only ten of these brilliant Simpsons characters for you. Based on their quotability, effect on the series overall, and their direct impact on America’s favorite cartoon family, these are the ten best Simpsons characters in the history of Springfield.