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.


Movies like Grandma’s Boy are what makes me excited to continue on with this project. The film blends every single element that makes a Happy Madison film a Happy Madison film and cranks it up to the nth degree: stupid cartoon caricatures masquerading as human beings; a recycled plot; lazy, unfunny jokes; mediocre-to-bad acting performances; and a forced romantic subplot between actors with barely any visible chemistry. The act of watching Grandma’s Boy was a miserable experience, but it was miserable in the most fascinating way imaginable.

To start, the film seems like it was born out of a junior high-level creative writing class. Admit it: The first time you heard about Google or Apple’s corporate headquarters being full of ping-pong tables and cereal bars and yoga classes, you immediately wanted to pack your bags and hop on the first plane to Silicon Valley. Grandma’s Boy takes that approach to the workplace and removes any semblance of realism. Maybe you didn’t grow up playing video games, but the film reads like a teenager’s vision of how adults spend their days making them. 

Other entries in this series surely have interesting stories behind the scenes, but I’ve never concerned myself too much with seeking them out. I’m intrigued to find out the casting decisions at play here, putting Allen Covert in the lead role when he’s normally relegated to sidekick or cameo duty. Grandma’s Boy remains one of the only HM films to not star either Adam Sandler or one of his main collaborators (David Spade, Rob Schneider, Kevin James, etc.), and it’s hard to understand why Covert’s role didn’t go to someone like Spade, for instance. Spade could easily fit into the arrested development in which Covert’s character finds himself. Spade and Schneider do make one-scene appearances, and Kevin Nealon yuks it up as a holistic weirdo, so it’s not as if this film was viewed as a black spot on the production slate.

The ace up Grandma’s Boy’s sleeve, though, is Linda Cardellini. Hollywood’s journeywoman could have easily shown up to collect a paycheck and wash her hands, but she gives it her all and makes it look like she’s having fun. Just watch the sequence where Samantha sings Salt-N-Pepa’s “Push It” and tell me she’s not the best part of this film. It’s unfortunate, but not surprising, that the rest of the film — including Samantha — is populated by crudely drawn characters who are reduced to their basest instincts. Would you believe me if I told you that everyone that works at a video game company is a nerdy virgin? Or that elderly women enjoy watching Antiques Roadshow? Or that drug dealers are eccentric screwballs?

In spite of itself, Grandma’s Boy succeeds (needless to say, I’m using that term lightly) because it does all of the things that have held back previous Happy Madison films. There’s rampant drug usage. There’s gratuitous nudity. There’s adult language. Sandler may consider himself a man of all people, and his films largely reflect that; they often aim to appeal to the largest demographic possible. There’s nothing wrong with this approach, of course. But by making a dumb, adult stoner comedy, Grandma’s Boy knows who its audience is and who will see it. In that regard, Grandma’s Boy has some semblance of ambition, and no matter how badly executed the end result is, that’s not something that can easily be said for most of the films in this project.

  • “I’m Getting Paid How Much?!” Inexplicable Cameo Award: Again, it’s nigh impossible to pick a cameo for this film because it’s almost completely devoid of any cameo appearances. It feels like the entire cast, save for Cardellini and a pre-Superbad Jonah Hill, is full of actors who typically appear in other films as cameos. Crucify me if you want, but I’m punting on this one.
  • Just Go With It: The Happy Madison Promise. The entirety of the video game office feels right at home in just about any HM movie, especially JP’s office, which is designed to look like a spaceship and has a ridiculous reclining chair and three computer monitors.
  • Fart Joke Counter: 2, plus a scene where Nick Swardson teaches another human adult how to fart with his armpits.
  • The Walkout Test: Absolute fail. I doubt the person in question would make it past the first 15 minutes.
  • NEXT TIME: Sandler returns in one of the most highly regarded films in this entire series, Click.