Once the poster-boy for gut-busting comedies, Adam Sandler is now the laughingstock of Hollywood filmmaking. How did the same guy behind comedy classics like Billy Madison, Happy Gilmore, and The Wedding Singer, go on to pump out soullessly insufferable schlock like Grown Ups, Jack and Jill, and Blended?

Sandler is one of the few actors on the planet whose name takes precedence over the films in which he appears. He is his own brand. He invented “Sandler comedy,” which is basically a genre of its own, where Sandler is doing his Sandler thing to the absolute max (and usually has some sort of larger creative involvement in the project as well). Billy Madison and Happy Gilmore? Absolutely, those are Sandler comedies. Punch-Drunk Love and Funny People? These films are what I would call “movies with Adam Sandler,” but not “Adam Sandler movies.” Looking at Sandler’s golden age (1995-1999), you’ll easily detect the common threads that define a Sandler comedy. While film snobs may not consider these movies to be “good” films, they are certainly good comedies. They make us laugh. They make us recite line after line. They make us happy.

However, these films are now also a distant memory, as today, the “Sandler comedy” is something entirely different. The sort-of-charming doofus that repeats school, the lovable slacker that takes up professional golf to support his grandmother, the clueless romantic with a heart of gold who sings at weddings? These guys are gone for good, replaced with a never-ending stream of self-indulgent characters that are more crude than funny. Sandler seems to have turned his back on the very types of comedic roles that made us fall in love with him. Despite its stupidity, Billy Madison has heart—in fact, all of the Sandler comedies had heart until roughly 2000, at which point his films became more and more like cringe-inducing attempts at comedy, rather than comedy gold themselves. These newer movies feel like paychecks, not films. His new characters are cold, offensive, and forgettable. The plots are aimless, yet predictable. These are bad movies.

There is no denying that Sandler has talent. He is not only one of the funniest comedians ever, but also, as reinforced by his acclaimed performance just this past year in The Meyerowitz Stories (New and Selected), a gifted dramatic actor. That just doesn’t disappear. But there is no denying that despite some successful risk-taking over the years, he has also made some very questionable career choices. This video chronicles Sandler’s career taking us to the pinnacle and charting the downward spiral that followed. Classic Sandler is still in there somewhere—he has to be! Let’s hope we see him again soon.

Career trajectories, like life, can be unpredictable! Join us as we take the long view on the work of some of our favorite movie stars, like Matthew McConaughey, Robert Pattinson, Ellen Page, and Greta Gerwig.