Lasciate ogne speranza, voi chi’intrate. How did it come to this? At the height of his power in Hollywood in 1999, Adam Sandler founded his own production company as a way to continue making the movies he enjoys. Over the years his films have slowly morphed into a pariah on the landscape of big budget studio comedies, becoming thinly veiled excuses for lavish vacations. But do they truly represent the nadir in the career of one of comedy’s once-brightest stars? Are there any hidden or underrated gems? Is there such a thing as too few fart jokes? Will I retain any sense of sanity by the end of this? Join me and find out, as we venture to the Happy Valley.

We haven’t had many opportunities to talk about auteurs in this series simply because it hasn’t felt applicable to many of the films so far. Sure, some of the earlier Happy Madison films were at least co-written by their directors (as in the cases of Little Nicky and The Hot Chick, for example), but those films never felt inherently born from their own visions. Mike Binder, who wrote and directed Reign Over Me, is the only example so far, but I’m unfortunately unfamiliar with the rest of his filmography. Funny People could only have come from Judd Apatow.

Apatow not only wrote and directed the film but used his long-standing relationship with Adam Sandler to craft a realistic story of success and failure. After experiencing a red-hot start to his film career with two of the biggest comedies of the mid-2000s in The 40-Year Old Virgin and Knocked Up, Apatow used his clout to make a deeply introspective film, and he cast Sandler as a fictionalized version of himself. The opening home-video montage was real footage that Apatow shot when the two were roommates in the early stages of their careers, which adds an extra layer of context to the later portions of the film.

I’ve always been fascinated with the mental preparations necessary for an actor to portray him or herself onscreen, and Sandler excels at making his George Simmons a scummy — but still likable — character. There will be far too many films to come in this series in which Sandler plays the same reductive, idealized version of the same person, but Apatow keeps Sandler in check. It’s important that we’re introduced to Simmons through the eyes of an up-and-coming comedian in Seth Rogen’s Ira Wright in order to get an accurate perspective on his career. Simmons enjoyed an early trajectory that’s eerily similar to Sandler’s, with inexplicably stupid films where he plays a mermaid and a baby. Sadly, we never really get Simmons’ thoughts on how his career played out. Does he regret his early work in big, dumb comedies? Does he long to create something with a more impactful message? Did he view them as a necessary evil to stay afloat in the cutthroat entertainment industry?

George’s narrative as a dormant comedian willing to stage a comeback after a grim medical diagnosis converges with a sort of riff on The Great Gatsby, as he tries to win back the love of his life (played by Leslie Mann, who is Apatow’s real-life wife) despite her seemingly perfect relationship with her husband (Eric Bana). Thrown into George’s orbit and drama is Ira, who dreams of success in comedy, without the baggage that the life entails.

One of the more boisterous complaints against Apatow has been the borderline-unnecessary length of his films. Funny People is his longest film to date, and while the criticism isn’t unwarranted, the film never feels like it’s wandering aimlessly. The lengthy runtime can certainly be attributed to Apatow’s improvisational approach; most scenes are only loosely sketched out, and the actors are responsible for their own dialogue and character beats. Are there a handful of scenes that could have been cut out or trimmed to make way for plot points that Apatow brings up but never fully resolves? The stand-up scenes never fully wear out their welcome, but I would have liked to see George’s relationship with his father fleshed out more. Sandler develops the idea of George’s constant search for approval early on, and it eventually falls by the wayside after the first act. The same could be said for the aforementioned scope of George’s career. We see a scene or two of Mann and Bana’s children watching George’s films, and it would have been nice to get a glimpse of George’s career between his rise to fame and the events of Funny People. Was he simply coasting on the goodwill of his earlier work, still working occasionally, or had he become a pariah amongst his peers?

Even so, Apatow populates his film with deeply flawed but likable characters. Few of the film’s plot developments feel forced or untrue to the people at their center. And how many films have we covered in this series where you’re left wanting to know more about the characters within them? We’ll never really know how much of George Simmons is a fabrication and how much is Sandler pulling from real life. We’ve seen a surprising number of memorable Sandler performances, but this may be my personal favorite so far in that Sandler is able to tap into a private, vulnerable portion of himself, a side that couldn’t have been easy to put out into the world.

  • “I’m Getting Paid How Much?!” Inexplicable Cameo Award: There’s literally a scene full of cameos of actors playing versions of themselves, including Norm MacDonald, Ray Romano, Sarah Silverman and Eminem. However, I have to show some love to Bryan Batt and Maggie Siff, who played Sal Romano and Rachel Menken in Mad Men, one of my favorite shows of all time.
  • Just Go With It: The Happy Madison Promise. I haven’t really talked about it yet, but I could probably cover an entire mini-essay on Sandler & Co.’s use of the homophobic F-word since Happy Madison’s inception, but it’s on full display here, once again.
  • Fart Joke Counter: None.
  • The Walkout Test: I’m gonna say this one’s a pass, despite all the talk of genitalia and masturbating, and I can’t exactly explain why. Hey, we live in an unpredictable world. Sometimes miracles can happen.
  • NEXT TIME: There’s so much to unpack with the horror film The Shortcut.