The Best Happy Madison (Adam Sandler’s Production Company) Movies, Ranked

Following the success of Big Daddy, his third movie in a row to gross over $100 million, star-friendly studio Sony offered Adam Sandler his own production company: Happy Madison, named after his breakout comedies Billy Madison and Happy Gilmore.

Sandler’s hot streak continued for years to come (between 1999 and 2011, only one live-action comedy he starred in, Little Nicky, failed to cross the $100 million barrier). Happy Madison also allowed him to employ his buddies, including, for better or worse, Rob Schneider, Kevin James, Allen Covert, and David Spade, whose new movie, The Wrong Missy, came out on Netflix this week. Despite an enjoyably unhinged performance from Comedy Bang Bang favorite Lauren Lapkus, The Wrong Missy does not appear on this list of the best Happy Madison movies. Maybe it’s due to my being a Sandler apologist, or because I love one-star movies that I enjoy like a five-star movie, but it was tough only choosing 10 titles from the filmography, which dates back to Deuce Bigalow: Male Gigolo (also not on the list). I already regret excluding The Master of Disguise. No, really.

Ready to begin? Terrific.

10. Grandma’s Boy


Grandma’s Boy might be the most Happy Madison movie. Look at that image! It’s two unconventional male leads in their 30s, one of whom is dating a woman ridiculously out of his league, smoking pot and playing video games next to a monkey. This, I should say, is not a bad thing. Some of the best Happy Madison movies are supremely stupid, and Grandma’s Boy is charmingly dumb. It stars Allen Covert as the titular grandma’s boy, a video game tester who lives with his grandmother and her friends after being kicked out of his house because his roommate spent the rent money on sex workers. Grandma’s Boy uses a different word to describe their profession, one of many lightly problematic things throughout the film (the racial politics: not great!). But it has the always-wonderful Linda Cardellini singing “Push It,” which forgives a lot of sins.

9. Sandy Wexler


One of my favorite things about Happy Madison movies is the random collection of people in the cast (Taylor Lautner, Steve Buscemi, and Vanilla Ice? You do you, The Ridiculous 6.). I mean, would you say “no” to Adam Sandler? Here’s the cameo list for Sandy Wexler, my favorite of Sandler’s straight-to-Netflix movies, for instance:

Jewel, Darius Rucker, Jason Priestley, Gary Dell’Abate, Arsenio Hall, Quincy Jones, Judd Apatow, Janeane Garofalo, Pauly Shore, Kevin Nealon, Lorne Michaels, Dana Carvey, Chris Rock, David Spade, George Wendt, Penn Jillette, Henry Winkler, Tony Orlando, Al B. Sure!, Brian McKnight, Vanilla Ice, Jimmy Kimmel, Conan O’Brien, Louie Anderson, “Weird Al” Yankovic, Kenneth “Babyface” Edmonds, Mason “Ma$e” Betha, Jay Leno, Lisa Loeb, Jon Lovitz, Budd Friedman and his wife Alix Friedman… Mike Judge makes a vocal cameo as Beavis and Butt-Head during the end credits. Professional wrestlers Rikishi and David Otunga have brief roles.

That is a wild assortment of vaguely to extremely famous people. Imagine the wrap party, with Conan and Jay Leno breaking Panera-catered bread, Henry Winkler talking about fish with Pauly Shore, Hootie and Jewel remembering the 1990s. Oh, to be a fly in that hypothetical scenario. Cast aside, though, Sandy Wexler is better than The Ridiculous 6, The Week Of (which has its moments), The Do-Over (which doesn’t), and Murder Mystery because, as Vulture‘s Jesse David Fox writes in his extremely thorough Sandler ranking, “the plot is just him going from one of his friends to the next and laughing at the ridiculous characters they’re doing.” Sandy Wexler isn’t a passion project in the traditional sense, but it’s a project full of passion for entertaining oddballs. It’s the most heartfelt of Sandler’s Netflix offerings, and maybe his entire filmography.

8. Click

Before writing this post, if you had asked me where I was going to rank Click, I would have said top five, easily. Maybe even in the top three. Then I re-watched Click for the first time in years, and unfortunately, it’s not as good as I remember. Even for a Happy Madison movie, there’s a lot of fat-shaming and gay jokes (at least Little Nicky had the “excuse” of coming out in the 1990s), and schlubby family-man sentimentality is never a good fit for Sandler. But Click has its moments and one terrific performance. No, it’s not that punk O’Doyle kid, seen for the first time since Billy Madison. It’s Christopher Walken as the mad scientist/angel of death who hands Sandler the universal remote control, in that it’s a remote that controls the universe (get it?). He leans into the character’s weirdness, delivering lines like “he’s always chasing the pot of gold, but when he gets there, at the end of the day, it’s just Corn Flakes” with an inspired specificity.

Another good thing about Click:


I love films.

7. 50 First Dates


Adam Sandler and Drew Barrymore have made three movies together: The Wedding Singer, which is great; Blended, which is bad; and 50 First Dates, which is… fine.

It’s maybe the movie on this list I’ve watched the most, due to it always being on TV, but the repetition does the romantic-comedy no favors. Sandler and Barrymore are cute together, but it’s tough to not question the premise, with Sandler’s Henry having to convince Barrymore’s Lucy to repeatedly fall in love with him after a car crash leaves her waking up every morning with no memories of anything that happened after the accident. The ending, which is supposed to be sweet but comes off creepy, is particularly uncomfortable: a confused Lucy wakes up on a boat, married to a man she doesn’t know with a daughter she doesn’t remember. But it’s to Sandler and Barrymore’s credit that they’re so likable together, they mostly pull this horror movie premise off.

6. Little Nicky


Little Nicky looks both extremely expensive and hilariously cheap, which somehow works in its favor. It’s a ramshackle affair about one of Satan’s three sons, Nicky (Sandler), traveling to Earth to trap his escaped brothers Adrian and Cassius (Rhys Ifans and Tommy “Tiny” Lister Jr.) in a silver flask, so the frozen gates of Hell can re-open… and their dad (Harvey Keitel) will stop disappearing… and also Nicky falls in love with Patricia Arquette… and Kevin Nealon has boobs on his head… and Dana Carvey plays a shrill-voiced basketball referee. It’s a lot, but it’s also nothing, a series of barely-connected, horn-dog (and horny dog) sketches that, frankly, I find it hilarious. If the Devil showing a pineapple up Hitler’s butt (crown-side first!) is wrong, I don’t want to be right.

5. Jack and Jill


Jack and Jill is the “chaotic energy” of Happy Madison movies. I mean:


In order, we have Regis Philbin complaining about having “such” diarrhea; Adam Sandler, as Jill, thinking Skype is an anti-Semitic joke, which is barely a joke; Adam Sandler, as Jill, squishing a small horse; Shaquille O’Neal in a ham commercial; Adam Sandler, as Jill, waving at a shirtless Adam Sandler, as Jack, while she’s sitting on the toilet; Johnny Depp wearing a Justin Bieber shirt at a Lakers game next to an in-disguise Al Pacino; Adam Sandler, as Jill, calling Jared Fogle (uh oh!) “Mr. Subway Sandwich” at a party; Al Pacino interrupting his own play to brag that he can “smell horny” from across the ocean; and the I Think You Should Leave car guy as a bathroom attendent.

The only thing crazier than the plot of this movie — where Sandler plays fraternal twins Jack and Jill, including a scene where (to quote one of my favorite Letterboxd reviews ever) “Al Pacino wants to bang woman Adam Sandler but woman Adam Sandler doesn’t want to bang him back so man Adam Sandler bangs him” — is that it made $150 million at the box office. Game Night, another studio comedy, was considered a huge hit in 2018, and it only made $117.7 million. Is Jack and Jill a good movie? No, of course not, but it’s laudably bonkers, and Sandler’s commitment to making Jill as annoying as possible is fascinating, in a perverse kind of way. Plus, it has the Dunkaccino rap.

Jack and Jill?


4. Mr. Deeds / Anger Management


I’m sorry, but I can’t separate the two. Not that they have much in common, other than coming out within a year of each other and making a ton of money, but they’re both in that “pretty good, but could have been better with some tweaks” area.

– The good in Deeds: Winona Ryder; the “Space Oddity” scene; “sneaky sneaky.”
– The bad in Deeds: the foot scene; the child abuse; making Peter Gallagher a bad guy.
– The good in Anger: JACK NICHOLSON.
– The bad in Anger: Rudy Giuliani (Sandler sure had some problematic favs!).

I wouldn’t go out of my way to watch either Mr. Deeds or Anger Management, but I wouldn’t click to another channel if I saw either playing at 3 p.m. on a Sunday, either.

3. The House Bunny


The House Bunny is my Legally Blonde. That is not a knock on Legally Blonde, a very good movie; it’s a compliment for The House Bunny. Both films have blonde female protagonists who aren’t taken seriously because of the way they look, but where Elle Woods must convince the stuffed-shirts at Harvard Law School that she’s worthy of being a lawyer, The House Bunny is about a former-Playboy Bunny who becomes the house mother for the least popular sorority on campus. It’s a low-stakes affair, but that’s what I like it about. There’s a lot you could read into The House Bunny, about ageism, sexism, and to not judge a book by its cover, but to the movie’s credit, I don’t think it’s aiming for messages. It’s an entertaining farce, anchored by a never-better Anna Faris and future-stars Emma Stone and Kat Dennings. “Instead of the Mahi-Mahi, can I get just the one Mahi, because I’m not that hungry?” is just funny, y’know?

2. Funny People


Funny People might be Adam Sandler’s definitive performance. More than Happy Gilmore, more than Punch Drunk Love, more than even Uncut Gems.

He’s extraordinary as George Simmons, a movie star making shitty-but-successful comedies like MerMan who returns to stand-up comedy when he’s diagnosed with acute myeloid leukemia, channeling the rage that’s simmering beneath the surface of most of his characters and his every-man likability. Seth Rogen, too, gives a top-tier showing as Ira Wright, who’s hired by George to write jokes for him at his comedy club gigs; I’d say it’s surprising, but Rogen has long been an underrated actor. Funny People suffers from many of the same problems as director Judd Apatow’s other films, particularly the excessive run time, but there’s an honesty to it, full of joy and anger and sadness, that you don’t get from a lot of wide-release studio films, let alone wide-release studio comedies. While it would have been fun to see Sandler as the Bear Jew in Inglourious Basterds, it wouldn’t have been revelatory, like he is (Eminem, too) in Funny People.

1. You Don’t Mess with the Zohan


While doing research for this list (watching Bucky Larson: Born to Be a Star), my 19-year-old half-brother asked me to name my favorite Adam Sandler movie. Billy Madison or The Wedding Singer or Uncut Gems, if that counts, I responded, before I turned the question back on him. “I know this is a weird choice,” he started, but I already knew what he was going to say, because I love it, too. You Don’t Mess with the Zohan isn’t my number one Adam Sandler movie, but it’s number one in the Happy Madison-verse.

Imagine the pitch meeting.

STUDIO HEAD: “Thanks for coming into today, Adam. What’s up?”

SANDLER: “So, I have an idea for this movie. It’s an action-comedy called You Don’t Mess with the Zohan. I play Zohan, an Israeli counter-terrorist who dreams of moving to the United States and becoming a hairdresser against the wishes of his parents.”


SANDLER: “I’m not finished. At the end of the movie, Zohan will unite the Israelis and Palestinians, and one day, someone will write ‘it’s clear Zohan loves the ladies, regardless of age or size’ on the movie’s Wikipedia page.”

STUDIO HEAD: “I’m not…”

SANDLER: “You Don’t Mess with the Zohan will make $200 million at the box office.”

STUDIO HEAD: “You son of a bitch, I’m in.”

Zohan is one of the few likable characters Sandler has played in the Happy Madison era, and because it’s a comedically heightened universe, where no harm comes from dropping a piranha in your Speedo, you also buy that impossibly-beautiful woman would throw themselves at him. It’s a winking improvement on, say, Kate Beckinsale being married to Sandler’s grumpy architect in Click, or Jessica Biel sincerely asking fake-gay firefighter Chuck to touch her breasts in I Now Pronounce You Chuck & Larry.

What’s the bigger shame? That Sandler and Judd Apatow, who co-wrote Zohan, haven’t worked together beyond the top two movies on this list, or that the superhero-like Zohan hasn’t been inducted into the Marvel Cinematic Universe yet (hey, it worked for another New York-based Sony character.) Has Captain America settled the Israeli-Palestinian conflict after decades of strife while styling women’s hair in his free time? He wishes.