On a list of the most financially successful movie comedians of all time, Adam Sandler would probably be fourth behind Eddie Murphy, Jim Carrey, and Mike Myers. Sandler has two of the top 25 highest grossing movie comedies with BIG DADDY and THE WATERBOY, two of his worst films. Yet, unlike those other three comedians, Sandler is often universally despised and panned by movie critics across the country.

Why? Because he’s just not particularly funny.

Sandler began his career on the great American movie career launching pad known as SATURDAY NIGHT LIVE. When Sandler joined the show, it was at its creative zenith, with brilliant characterizations by Dana Carvey, Phil Hartman, and Mike Myers clogging popular culture.

However, unlike his predecessors, Sandler never created characters as much as he created caricatures. Canteen Boy and Opera Man were not anything other than vessels for Sandler’s fearless and incessant mugging. Skits featuring Sandler no longer revolved around actual jokes, but rather ideas for jokes. The humor usually involved Sandler making a funny face while essentially winking at the audience, saying: yeah, this is goofy and weird and makes no sense … but isn’t that cute?? It helped that Sandler had that everyman boyishness that felt appealing to both sexes. His malignant influence on the show is still felt long after he left, allowing nonsensical “comedians” like Andy Samberg to thrive.

Sandler’s goofball-next-door appeal gave him instant-stardom once he left SNL to do movies. His first films were tailored to suit his SNL persona. BILLY MADISON is barely a film, featuring Sandler as a man-child goofing around with cute kids. It was, of course, a huge hit.

Sandler’s next film, HAPPY GILMORE, was substantially better, and is probably one of the best things Sandler has ever done. Again we see the repressed child-man, this time in a sports environment. Despite the improvements, the film would be much less successful had the Bob Barker fight been left out of it; it is the highlight of the film.

After that, Sandler’s filmography takes a sharp nosedive. LITTLE NICKY and THE WATERBOY are awful films. THE WEDDING SINGER is probably the best comedy of his career, although most of the fun comes from nostalgia rather than earned laughs.

Following this, Sandler attempted to make a move into more serious territory (a la Robin Williams) with PUNCH DRUNK LOVE and SPANGLISH. The films were mismarketed as comedies to appeal to Sandler’s fan base. They show Sandler trying to stretch into dramatic territory, and he showed a surprising amount of range and ability.

Sandler’s newest, FUNNY PEOPLE, has again been marketed as a comedy, but it is not particularly funny. Sandler takes his hung-dog persona through the idea of dying young, with mixed results. One cannot help but notice how the jokes seem to choke when coming out of Sandler’s mouth, as if his heart is not in it.

Sandler’s biggest problem throughout his career is a lack of understanding about his truest gifts. He has a good presence onscreen, and the anger that has always festered below his surface works to his advantage in serious roles. But Sandler has never shown any impressive comedic timing, and even less comprehension of comedy in general. Most of his comedic work mines nostalgia and popular culture for laughs, rather than genuinely earn them (much like Mike Myers).

Sandler is no longer the slumping, mumbling kid on SNL. He has grown into a quieter, pudgier adult with some  complicated personality quirks. It’s time to leave the comedy for the talented young, and move into more serious middle-aged films for middle-aged people.