Every Adam Sandler Comedy, Ranked

Adam Sandler has never been a critical darling. This information is practically a cliché; even the movies now regarded as his early, funny ones didn’t exactly receive glowing notices during their original runs, and as the audience that enjoyed his early comedies aged into possible critical-establishment roles, they, too, came to lament the low quality of his vehicles. As a former fifteen-year-old, I think I can attest that this isn’t just grumpiness or nostalgia setting in: I dutifully see Adam Sandler comedies not because they’re usually good, but because they can be good, and I want them to be good. Regardless of what we pointy-headed types may look at as diminished returns, Sandler has remained a popular movie star (in his comedies, at least) for close to twenty years by this point. He may not have hit the same box office or critical highs as fellow SNL players turned movie stars like Will Ferrell or Mike Myers, but in terms of pure numbers, he’s probably the most financially successful (depending on how you count Eddie Murphy’s more erratic mix of massive hits and huge flops).

Though they do vary in quality, it’s his consistency that has come to define his career. The sheer uniformity of his output remains almost unmatched: the vast majority of movies starring Adam Sandler come from his Happy Madison production company, with multiple writing, directing, and/or producing credits from Sandler’s usual gang of buddies, associates, and hangers-on (for these purposes, movies made with Sandler’s usual screenwriters, producers, and/or directors before the official creation of the Happy Madison shingle count towards that total).

This includes the twenty-one movies that I’ve fudged into a top (or bottom) twenty below. This list does not include the more serious movies he has made for other people every two to four years (Punch-Drunk Love; Spanglish; Reign Over Me; Funny People); his voiceover work in Hotel Transylvania (borderline, because it features Sandler’s buddies in supporting roles and a co-writing credit from Robert Smigel, but is also very much of the Sony Animation house style and presumably would have been made without Sandler’s participation); or his sole action-comedy, Bulletproof. Sandler also did supporting roles in a couple of unsuccessful comedies in 1994: Airheads and Mixed Nuts. I have seen them both; let’s leave it at that.

For each Official Adam Sandler Comedy, I’ve included notes on which of Sandler’s team of SNL writers (most often Tim Herlihy; sometimes Fred Wolf, Robert Smigel, or Steve Koren) and journeyman directors (Dennis Dugan, Frank Coraci, Peter Segal, Steve Brill) get credit, along with counts of how many SNL performers he manages to hire. I have not included Allen Covert, Peter Dante, or Jonathan Loughran in these counts; just assume that all of them are in all of these movies and that Covert produces most of them, even if that’s not literally true. I’m also avoiding doing a Nick Swardson tally. He’s been in eight of these. It feels like more. Finally, I’ve noted Sandler’s myriad love interests, not only because they represent a surprisingly and weirdly diverse cross-section of name actresses from the past few decades, but also because it’s worth noting how many of them are significantly younger than he is, even (especially) when he’s playing a total man-child.

Sandler’s consistency makes the task of ranking his films perhaps even more fruitless than the usual list-making; both his best and his worst can be considered toss-ups, especially when you subtract the easy outs of Punch-Drunk Love and Funny People, which are the two best movies he’s actually appeared in. But closer study does reveal not just the way Sandler repeats himself, but the way his repetitions accommodate subtle shifts, occasional jumps in quality or particularly ill-advised detours. (Longer essays or reviews I’ve written about some of these films are linked to their titles, when available.)

Herewith, your intro to those Adam Sandler studies.

20. Grown Ups

Year: 2010
Sandler Crew: Dennis Dugan directs; Sandler and Fred Wolf co-write.
SNL buddy count: 8: Chris Rock, David Spade, Rob Schneider, Maya Rudolph, Tim Meadows, Colin Quinn, Norm MacDonald, and Jon Lovitz.
Love interest: Salma Hayek, exactly one week older than Sandler.
Starting at the bottom: Sandler and his buddy write a “movie” about their buddies sitting on lawn chairs doing limper riffing than you’d ever expect from professional comedians, and they hire another buddy to film it. This could describe any number of Sandler movies to any number of people, but Grown Ups, a reunion movie clearly about people who (beneath the tissue-thin veneer of their “characters”) see each other all the goddamn time. If not for the distinct lack of energy on display, it could be some kind of horrible dream project Sandler might have cooked up in his SNL days. It stars all of the SNL guys he came up with, right down to the ghost of Chris Farley, who you can picture hovering somewhere above the head of Kevin James, a physically astute but far less inspired performer and an honorary member of Happy Madison’s SNL Dude Club. It remains one of his biggest hits ever, which implies that maybe for some people besides Sandler, this was actually the movie they dreamed of as teenagers watching “their” SNL crew, rather than a sad, flaccid nightmare version that makes you feel kind of stupid for liking any of these guys in the first place.

19. Eight Crazy Nights

Year: 2002
Sandler Crew: Sandler is joined by frequent supporting player Allen Covert, along with two other writers, on the screenplay.
SNL buddy count: 3; the voices of Rob Schneider, Kevin Nealon, and Jon Lovitz.
Love interest: Sandler’s wife Jackie; eight years younger, but, you know, fair enough.
I have a sneaking suspicion that a rewatch of this movie could send it even further down the list, and the fact that I’d probably sooner watch almost any other Sandler picture again should do the job on its own. But as ugly, gross, and mostly laugh-free as this PG-13 cartoon in which deer eat shit absolutely is, I can’t deny the minimal effort that went into creating a Sandler-centric animated comedy about Hanukah. At the time, I still enjoyed far more of Sandler’s movies than not, so in 2002 this one was a bizarre harbinger of things to come.

18. The Longest Yard

Year: 2005
Sandler Crew: Peter Segal, a relative latecomer to the Sandler rotation, directs.
SNL buddy count: Chris Rock, Tracy Morgan
Love interest: None!
This is maybe Sandler’s straightest so-called comedy; remaking the prison football comedy, he treats the material more or less as a sports movie with a few mild laugh lines. There’s some shtick, but more often than not, it’s incidental to the story and, uh, emotions. It’s not a good look on him — which is strange, because just six months before this movie came out, Spanglish, featuring a perfectly credible dramatic performance from Sandler, was released to critical and audience hostility. The hostility is deserved; the movie is a mess. (If you want to watch a maligned late-period James L. Brooks movie featuring Stars of Today, I recommend How Do You Know? instead.) Sandler is also good in another unholy mess of a movie, Reign Over Me. But much of his straight-man work in his own productions, which started out looking like a generous ceding of laughs to his usual gang of crazies, has become dispiriting — they don’t even have the energy or conviction of a mess. The Longest Yard remade with a younger Sandler’s Waterboy-ish madness might have been something. Instead, it’s a movie under the sad impression that it has some kind of street cred.

Grown Ups 2

17. Grown Ups 2

Year: 2013
Sandler Crew: Dugan directs; Sandler, Herlihy, and Wolf co-write.
SNL buddy count: 16! Deep breath: Rock, Spade, Rudolph, Meadows, Quinn, and Lovitz return, plus Cheri Oteri, Ellen Cleghorne, Andy Samberg, Jorma Taccone, Akiva Schaffer, Bobby Moynihan, Paul Brittain, Taran Killam, Will Forte, and Melanie Hutsell. Somehow this both sets the record for the most appearances from Saturday Night Live cast members in a motion picture and does so without the crucial participation of Mr. Rob Schneider.
Love interest: Hayek again.
This probably seems like heresy, claiming that Grown Ups 2 is actually the rare sequel to surpass the original. But I wouldn’t say it surpasses so much as gives up earlier, which lends it just the faintest dusting of the mildest possible charm. The movie is straight up a day in the life of Sandler and his buddies from the first movie (minus Schneider) as they tool around on their kids’ last day of school before summer vacation. The aimlessness of this premise, lord help me, is actually kind of appealing. Less so: the scene where, uh, David Spade goes down a hill in a CGI spare tire for some reason. Or the scenes where Maya Rudolph angrily and triumphantly harangues a woman for looking like a man. One way it unequivocally tops the first movie: it has even more SNL alumni than Grown Ups — more, in fact, than any movie, including previous record-holder Coneheads (per my research, Sandler productions currently hold five of the top ten SNL-heaviest movies). This makes the exclusion of Schneider — allegedly over shooting conflicts with his CBS sitcom that may or may not have already been cancelled when this movie went into production (easier to believe considering the movie feels like it was shot two or three weeks before release) — sting all the harder. For Schneider, I mean. For the audience, I suspect it’s pretty much fine.

16. I Now Pronounce You Chuck and Larry

Year: 2007
Sandler Crew: Director Dennis Dugan.
SNL buddy count: 5: Dan Aykroyd, Rob Schneider, David Spade, Rachel Dratch, and Robert Smigel.
Love interest: Jessica Biel, sixteen years younger.
For years, I Now Pronounce You Chuck and Larry was the only Sandler vehicle I hadn’t seen, mainly out of homophobiaphobia. I knew that the movie would ultimately more-or-less endorse gay marriage, or at least the idea that gay people are also human beings, but the idea of eighty minutes of gay-panic laffs chased with a Sandler-sponsored lecture on tolerance sounded fishy and possibly opportunistic. Indeed, when I finally caught up with this movie in full last week, my queasiness was somewhat justified with the movie’s series of… gags, are they?… about how the young son of Larry (Kevin James) is obviously (and stereotypically) homosexual, much to Larry’s consternation. That said, the movie does have a vaguely sweet turn taken by Sandler’s Chuck, the coarser ladies-man firefighter who resists the proposal from his Larry that they marry to fix a paperwork snafu that would leave Larry’s kids high and dry in the event of his untimely death (except probably not, by almost any benefits-related regulation). Chuck is the character who learns a touching lesson about not saying “faggot,” but more unexpected is the way he happily takes to the fake marriage, encouraging Larry’s son in his musical theater pursuits and insisting that he and Larry share a bed. This almost — almost — counteracts the peak of Sandler’s self-casting in the role of an inexplicable ladies’ man, a later-career development that has never made a lick of sense. And this is an actual statistical peak, since Sandler is at one point seen luxuriating in the afterglow of what looks like an eightsome. But he does renounce his man-whoring ways to settle down with a love interest played by Jessica Biel, setting a record for age difference in a Sandler film. What the relatively sweet message doesn’t counteract at all is how shamelessly few laughs there are in I Now Pronounce You Chuck and Larry. Like 50 First Dates and Click, it’s sometimes questionable that Sandler is even attempting a full-on comedy; unlike Dates or Click, the serious stuff isn’t particularly interesting.

15. Just Go With It

Year: 2011
Sandler Crew: Director Dennis Dugan.
SNL buddy count: 2; only Kevin Nealon and Rachel Dratch.
Love interest: Jennifer Aniston, three years younger.
Chuck and Larry featuring the peak of Sandler’s onscreen lothario work by no means indicates that he put it to rest. As recently as Just Go With It, he was positioning himself as a connoisseur of one-night stands, albeit one created by Wedding Singer-style heartbreak in his youth. But the womanizing stuff may not even be all that noticeable, drowning as it is in a swamp of additional self-regard; in Just Go With It, Sandler plays a rich, successful plastic surgeon who falls in love with Brooklyn Decker and must convince her that he really is divorced from Jennifer Aniston (actually just his employee!) during a luxurious Hawaiian getaway. It’s unusual that we get to see movie stars’ conspicuous consumption right up there on the screen in front of us, so in this respect the movie has a queasy novelty. It also has some OK Sandler-Aniston chemistry, and a funny cameo from Nicole Kidman, one of Sandler’s occasional prestige cameos balancing out the non-acting likes of John McEnroe and Dave Matthews, who appears here to no great effect.

14. Bedtime Stories

Year: 2008
Sandler Crew: Tim Herlihy with a co-screenwriting credit.
SNL buddy count: Schneider stands alone.
Love interest: Keri Russell, ten years younger.
Sandler has clear kid appeal, from his rambunctious clowning on SNL to his ability to fit back into the grade-school classroom in Billy Madison. Even his more adult-oriented comedies tend to operate with a kiddie-movie sense of good guys, bad guys, acceptable mischief and genuine misbehavior, and I suspect that most of his movies of the past decade at least have been treated as de facto family outings by guys like Sandler himself: youthful during his SNL years, finding solace in his early comedies, and now familied up and happy to share the suggestion of laughter. In any case, Sandler gets out there; I remember my wife’s then-tween cousin informing me, a couple of years back, that Sandler and Schneider are the funniest guys in movies. Maybe that’s why the idea of Sandler doing a proper family film feels redundant, and why Bedtime Stories, released by Disney and directed by Adam Shankman (a journeyman technically outside the Sandler cabal, though well within their range of skills), actually made slightly less than the average Sandler comedy, rather than a Night at the Museum-style family bump. This just slightly more kid-friendly vehicle at least provides a respite from some of the lazy grossness that permeates his work of this era, at least to my recollection. My other major recollection of this movie involves laughing a lot at a thief played by Rob Schneider running away and clicking his heels together in the air while doing so. Bedtime Stories: in which Schneider finally got the biggest laugh.

Jack and JillSandler redo

13. Jack and Jill

Year: 2011
Sandler Crew: Director Dennis Dugan; co-screenwriters Steve Koren and Sandler himself — and Robert Smigel supposedly did some uncredited script work, too.
SNL buddy count: 5: Rob Schneider, David Spade, Tim Meadows, Norm MacDonald, and Dana Carvey.
Love interest: Katie Holmes, twelve years younger.
The very idea that Sandler might play his screeching, sweating, meddling twin sister in a drag performance opposite the privileged suburban asshole that has become his default role seems to have doomed Jack and Jill to Worst Movie Ever status, nevermind Worst Sandler Movie status. And fair enough: this is the apex of Sandler starring in a movie that looks like something he parodied in Funny People. But I cannot hate Jack and Jill; it represents too much effort on Sandler’s part, at least on the Jill side, however misguided. It’s a caricature of a performance, yet it also represents the id of Sandler’s enfant terrible persona: loud, abrasive, and crass. These are not exactly good things, but in a weird way, Jill’s deli-loving cartoon of awkward stereotypical Bronx Jewishness has, lord help me, a heart — at least more of one than the “nice” rich asshole Sandler dredges up again for his straight-man role. The movie also benefits greatly from Al Pacino playing himself in a supporting performance that goes beyond mere self-parody into a kind of deranged performance art that goes far beyond winking at some old Pacino movies (he becomes romantically obsessed with Sandler’s Jill and pursues her with great, terrifying zeal). Sandler has always embraced product placement in his films; Jack and Jill turns its product placement into a subplot about product placement that positions product placement as a vital component of job-saving (Sandler’s ad man will save his crew’s jobs if he works out this deal, you see), and, as a result, endgames in Al Pacino rapping about Dunkin’ Donuts. It’s pretty stupid. It’s also a little bit hilarious (and Pacino’s post-commercial reaction makes me laugh even more). Robert Smigel did not receive screenplay credit, but is credited on Pacino’s rap. That should tell you everything and nothing all at once. I can’t in good conscience recommend that you see Jack and Jill, but I can say that it’s an experience unlike any other, an increasingly rare feat in Sandler’s late-period comedies.

12. Anger Management

Year: 2003
Sandler Crew: Sandler crew member-to-be Peter Segal.
SNL buddy count: 1; just Kevin Nealon. Maybe it’s the presence of Jack Nicholson that veers the supporting/cameo cast more towards the character actor beat: Sandler semi-regular John Turturro, plus John C. Reilly, Luis Guzman, Woody Harrelson, and Harry Dean Stanton (!).
Love interest: Marisa Tomei — two years older!
Anger Management should have been an easy layup. Sandler plays a put-upon guy prone to outbursts of fury sentenced to work with an unpredictable, volcanic anger-management coach played by Jack Nicholson. It practically writes itself — or would have, if the movie didn’t weirdly downplay Sandler’s usual persona by having him get goaded, even tricked, into his outbursts by Nicholson, having the plot turn on the character’s repression rather than Sandler’s untamed nuttiness. It’s a sadly domesticated version of a potentially great idea. Despite bringing in Peter Segal, who made the only good Spade-Farley movie Tommy Boy, and a better-than-average crew of supporting actors who goose the laughs a bit, Anger Management remains the sum of a few decent set pieces: Sandler getting into a violent confrontation with a monk played by John C. Reilly; Nicholson and Sandler singing a West Side Story duet; John Turturro, whenever he’s around.

11. Click

Year: 2006
Sandler Crew: Director Frank Coraci.
SNL buddy count: 2: Rob Schneider and Rachel Dratch.
Love interest: Kate Beckinsale, seven years younger.
Click is a high-concept comedy wherein Adam Sandler discovers a magic remote control that allows him to pause, fast-forward, or rewind his life, and learns lessons — and as a comedy, it’s as wan as many of his mid-aughts period: trying too hard to be a real movie to concoct goofy tangents. What’s kind of fascinating about the movie, not so much in a way that makes it worth rewatching or necessarily watching at all but in a way that makes it better than some of Sandler’s equally wan films, is the way it goes pretty dark to teach Sandler’s character lessons about savoring, rather than fast-forwarding through, his life. The future he arrives at via fast-forwarding is full of regret, death, and grotesquerie, and while Frank Coraci is probably not the guy to really make this tonal lurch into something special, well, hey, points for trying.

10. 50 First Dates and Blended

Year: 2004/2014
Sandler Crew: Director Peter Segal on Dates; ol’ buddy Frank Coraci on Blended.
SNL buddy count: For Dates, it’s 3: Rob Schneider, Dan Aykroyd, Maya Rudolph; Blended, remarkably, only has Kevin Nealon.
Love interest: Drew Barrymore, nine years younger.
Sandler’s reunions with his Wedding Singer costar Barrymore aren’t nearly as funny as the first teaming; like Anger Management and The Longest Yard, the inspired premise of 50 First Dates comes from a pre-existing screenplay, given an uncredited slapdash once-over by the Happy Madison rewrite crew. What redeems it is the chemistry between Sandler and Barrymore; besides Emily Watson in the non-Happy Madison Punch Drunk Love, Barrymore is the only actress who’s ever really made sense opposite Sandler in a major way. In Dates she plays a typically sweet gal with a short-term memory problem: every time she wakes up, her memory resets back to the day of a car accident that gave her this brain injury years ago. Sandler plays a (yep) womanizer whose heart she melts, and who he attempts to woo despite an obstacle that seems insurmountable. It’s to the movie’s greatest credit that it doesn’t invent a ridiculous solution for him; instead, it touches on ideas about love and commitment. Heady stuff for a Happy Madison production. The jokes, though: yikes, mostly. Sean Astin plays a lisping guy on steroids. Rob Schneider gets horrible injuries. A walrus vomits on a mannish lady who assists Sandler at his zoo job. The bitter and the sweet mixture could use a few more stirs, but Sandler and Barrymore are charming together, as always. Their chemistry holds up for the brand-new Blended, which may actually be a touch funnier than Dates, and if it’s not as affecting, it also isn’t quite as schmaltzy as Sandler’s other feints toward family-friendliness. Sandler and Barrymore play single parents mismatched on a blind date who wind up on vacation together with their kids. The movie is more cute and amusing than hilarious, but it’s surprisingly restrained in terms of the sourness, self-satisfaction, and grossness that define a lot of Sandler comedies from recent years. The least convincing aspect, in fact, is that Sandler and Barrymore are supposed to hate each other at first; it’s a rom-com convention they can’t quite sell, because they’re such a natural fit. I appreciate that they haven’t overkilled the Sandler-Barrymore team-ups, but if Barrymore can raise his game this much (which is to say, more than most of his costars but less than Judd Apatow or Robert Smigel), maybe they should consider going back to the well a little more often.

9. Big Daddy

Year: 1999
Sandler Crew: Director Dennis Dugan, plus co-writing credits for Sandler and Herlihy.
SNL buddy count: 1: Schneider stands alone.
Love interest: Joey Lauren Adams, two years younger.
In 1999, Big Daddy was a post-Waterboy victory lap. It also remains, to this day, Adam Sandler’s highest grossing movie. Supposedly adjusting for inflation puts The Waterboy ahead, but then, this also illustrates the fallacy of simply “adjusting” for inflation. The Waterboy made $161 million from November 1998 through April 1999. Big Daddy picked up in June 1999, and made $163 million during its release, which lasted through October 1999. Yet somehow, I assume due to their difference in calendar year, Box Office Mojo interprets Waterboy‘s grosses as $16 million higher in “today’s” dollars, even though their releases were all but continuous (and presuming that theaters did not institute a ticket-price raise specifically timed to the release of Big Daddy). Regardless of how you count it, though, this remains a monumental period in the history of Adam Sandler: For the twelve-month period beginning in November 1998, only May passed without a Sandler movie in at least some theaters (though in many ways, the consistency of the ten-year run that followed is even more impressive). Big Daddy is also an important component of Sandler’s rise to comedy-star domination because of the way it introduces a stubborn sentimental streak into his work. Almost all of his comedies have this to some degree, but Big Daddy aspires (and mostly fails) to evoke the actual world in a way that an eighties-converging “1985,” hand-eating alligators, alligator-eating Cajuns, and hallucinated penguins do not. But before it gets into hoary custody-battle courtroom stuff about Sandler’s illegal adoption of a nauseatingly adorable moppet, Big Daddy is an agreeably silly little movie about growing up and taking responsibility for another person; it’s like a crude rough draft of the kind of movie Sandler’s buddy Judd Apatow would come to specialize in.

8. The Waterboy

Year: 1998
Sandler Crew: Director Frank Coraci; another Herlihy/Sandler screenplay
SNL buddy count: 1: Schneider. Just Schneider.
Love interest: Fairuza Balk, eight years younger.
I’ve followed box office results since I was about ten years old, which is to say I’ve been following box office longer than Adam Sandler has been starring in feature motion pictures (if we can agree that Going Overboard does not count as a feature motion picture, and I think we can). I remember USA Today publishing a surprised article in their Life section when Billy Madison unexpectedly topped the box office (albeit in a low-competition, low-stakes weekend) in 1995, and I very much remember the shock when The Waterboy opened to $39 million or so in November 1998 — at the time, one of the biggest comedy openings ever, and the last time analysts would be truly surprised by a Sandler comedy’s box office over-performance. The Wedding Singer was a hit nine months earlier, but this movie made twice as much, marking the moment when Sandler’s presumably teenage/college-aged following coalesced into just plain popularity. Weirdly, The Waterboy was the weakest “official” Sandler production to that point: not as weird or mangy, a little more sentimental, and no Steve Buscemi. In retrospect, though, the simple pleasures of Bobby Boucher screaming in anguish as he hurtles toward bigger, beefier football players, tackling them with possessed fury have a certain Sandler-world poetry, even an innocence. I didn’t laugh much at the time, but I admit: I think of this movie and I smile.

Buscemi crazy eyes

7. Mr. Deeds

Year: 2002
Sandler Crew: Director Steve Brill and screenwriter Tim Herlihy.
SNL buddy count: Again: just Schneider — maybe playing the same delivery guy he played in Big Daddy? In any event, this movie is just one brief Schneider cameo away from being the only Sandler movie with an SNL-buddy count of zero.
Love interest: Winona Ryder, five years younger.
Returning to movie screens chastened for reasons that we’ll get into in just a few list-spots, Sandler’s character in Mr. Deeds is a clear mish-mash of past Sandler shtick, both comic and not: he randomly beats people mercilessly a couple of times, like Happy Gilmore; he’s a modest small-town guy, like Bobby Boucher; he’s an heir to a fortune, like Billy Madison (though unaware of that fact until the movie, a loose remake of a Frank Capra picture, kicks its plot into gear). Mr. Deeds also probably represents the best use of a developing Sandler strategy where he lets others take care of the movie’s laughs: hence Steve Buscemi as a lovable townie called Crazy Eyes, and John Turturro as Sandler’s “sneaky” butler. Sandler was easing back into his comedy career during a busy year: after Deeds hit big as a summer release, fall of 2002 saw the release of his first dramatic role in Punch-Drunk Love and his animated pet project Eight Crazy Nights. As ambling stop-gaps go, though, Mr. Deeds is pretty funny, if uninspired.

6. That’s My Boy

Year: 2012
Sandler Crew: None, officially, though director Sean Anders seemed for a time like he might climb aboard.
SNL buddy count: 4: Andy Samberg, Will Forte, Rachel Dratch, and Ana Gasteyer — a group notable for containing zero SNL cast members from Sandler’s era of the show.
Love interest: None, actually; this is basically a no-girls-allowed club. To be fair, though, “none” is probably the second-best possible result after “Drew Barrymore.”
That’s My Boy was, somehow, Adam Sandler’s first R-rated Happy Madison comedy. Like peers Jim Carrey and Will Ferrell, Sandler seems like he would be funnier unleashed in a torrent of outrageousness and swears and, like both of them (especially Carrey), his audience is too teenage and/or family-oriented to actually make R-rated comedies financially viable (Ferrell has managed to bank a few, but his biggest productions are usually PG-13). Buy by 2012, R-rated comedy was a consistent enough box office performer that Sandler actually took kind of a risk for once with his raunchiest and most potentially abrasive movie since Little Nicky. It also grossed the least amount of money for a broad Sandler comedy since Nicky, and got similarly terrible reviews. I admit I was a tiny bit shamed by this article in Nathan Rabin’s My World of Flops series, describing the movie, with basic accuracy, as depraved, offensive, and weirdly self-congratulatory. It’s true that even playing a boorish fuck-up of a character, Sandler maintains a weird insistence that he be irresistible to women and beloved by everyone who gets to know him, but this is also a clever inversion of the intended formula, where an uncouth relative or buddy wreaks havoc on a normal guy’s staid life. Rather than being appalled by his long-estranged father (masquerading as an old buddy, naturally), the friends and family of Andy Samberg’s character pretty much embrace him — which creates even more of a nightmare. The movie is often nasty and mean-spirited, and like even some of the better late-period Sandler movies, it’s scattershot and overlong — not a good combo. But so help me, it made me laugh pretty consistently. It plays a bit like an alternate future for Sandler, like if he had followed the Little Nicky path instead of the Big Daddy path. So maybe the next movie on this list shouldn’t be a huge surprise…

5. Little Nicky

Year: 2000
Sandler Crew: Director Steve Brill, co-writing along with Sandler and Herlihy.
SNL buddy count: 6: Dana Carvey, Jon Lovitz, Kevin Nealon, Michael McKean, Robert Smigel, and, of course, Rob Schneider.
Love interest: Patricia Arquette, two years younger.
After basically doing a feature-length hybrid of Cajun Man and Canteen Boy for The Waterboy, Sandler turns to a less popular (it turns out, presciently so) character in his repertoire: Gil Graham, who appeared on Weekend Update to offer concert reviews that would mutate into a description of a terrible mishap revealing that he missed most of the concert. Sandler’s Nicky, the son of the Devil (Harvey Kietel!), is a good-hearted kid with a mouth twisted into a permanent grimace and Gil Graham’s whisipery whine of a voice. A lot of people, even fans, found this decision understandably off-putting, and Nicky fell down to early-Sandler box office levels. But it also hits early-Sandler levels of surreal anarchy with bizarre gags about hell, Satan worshippers, talking dogs, and devil spawn running wild in New York. Not all of it works, but inviting a bunch of his buddies down to the visual effects playground (this was his SNL-heaviest cast to date) seems to have given Sandler and company an infusion of anything-goes energy. Maybe this explains the bizarre return to gay-bashing (Nicky’s two metalhead buddies refer to his roommate as “Liberace,” “Elton John,” and so on. Ha?) after a sweet gay relationship wasn’t a big deal in Big Daddy — he was on top of the world and no one could tell him what was in bad taste! On the plus side, this means Little Nicky includes a joke about devils lowering the drinking age to ten, complete with a cut to a couple of ten-year-old bros emerging from a bar and vomiting on the sidewalk. Reader, I laughed. With its playful excess and flop status, Little Nicky is the remainder of the turning point that began with Big Daddy. After putting out four comedies in less than three years, he took a slight break before turning to his regular-guy-with-a-violent-streak shtick with Mr. Deeds. Eventually the temper tantrums were dropped in favor of a house in the suburbs and precocious kids. It must have been a hell of a contrast, staring at the returns on the sentimental, lower-key Big Daddy, next to the wilder, weirder Little Nicky, and I have to assume those movies in tandem set Sandler on his path for the next decade-plus.

4. You Don’t Mess with the Zohan

Year: 2008
Sandler Crew: Director Dennis Dugan, and Sandler is joined on the screenplay by two of his more distinctive buddies: Robert Smigel and Judd Apatow.
SNL buddy count: 4: Schneider, Smigel, Kevin Nealon, and Chris Rock.
Love interest: Emmanuelle Chriqui, eleven years younger.
I had fallen so far out of the Sandler habit with Chuck and Larry that I actually didn’t see You Don’t Mess with the Zohan until several weeks into its theatrical run, which is a long time for me regarding any movie I actively intend to go see. The trailers for Zohan did the movie no favors, but it is easily — easily! — the best Sandler comedy of the past seventeen years. I have written about it extensively elsewhere and am in danger of overselling it, so I should admit up front that it’s hit-and-miss, overlong, and sometimes dumb. But you can also feel a palpable difference between a script that Sandler writes with Robert Smigel and (at some point) Judd Apatow and one his crew of bros rewrites from the high-concept pile. You Don’t Mess with the Zohan is simply so much weirder than almost anything Sandler has created for himself: he plays a near-superhuman Israeli counter-terrorist who fakes his own death and gives up fighting to become a hairdresser in New York, only to have his past life haunt him as he falls in love with a Palestinian girl. So, yeah, it’s a comedy about the Israel-Palestine conflict. It indulges plenty of Sandler tropes — namely giving his characters great facility with both violence and lovemaking — but pushes them so far that they actually become funny — weird on purpose, not just weird vanity. Zohan also engages with Sandler’s Jewishness like nothing he’s done outside of Eight Crazy Nights (though Jack and Jill goes there a little, too), shows real love for the cultural stew of New York City, and has plenty of identifiably Smigel-ish absurdities. Yes, it has too much Nick Swardson, and yes, it has Rob Schneider, but it also has John Turturro hamming it up as Sandler’s insane arch-nemesis, and more laughs than anything Happy Madison has done since before it actually existed.

Happy Gilmore

3. Happy Gilmore

Year: 1996
Sandler Crew: Dugan, Herlihy, Sandler: the dream team, apparently.
SNL buddy count: 2: Nealon and Smigel.
Love interest: Julie Bowen, four years younger.
Happy Gilmore introduces pretty much every Adam Sandler trope not already explicitly covered by Billy Madison or his work on Saturday Night Live: The bizarre but here still entertaining idea of him as a violent young man with a hair-trigger temper; the sweet-Jewish-boy sentiment (and fascination with goofy old people) inherent in trying to save his grandmother’s home; and the idea of product placement as not just something to be grudgingly tolerated, but openly celebrated (it’s a major late-breaking plot point). Within the framework of a sports movie about an athlete who needs to train and learn discipline, it all plays pretty well, featuring inspired sequences like Sandler getting into fisticuffs with Bob Barker (as himself, naturally) and the nursing home secretly run (by a supporting Ben Stiller) as a cruel sweatshop. There’s an underdog scrappiness to this movie that the Happy Madison team (named for Sandler’s first two hits) has tried to recreate a number of times since, to mixed-at-best effect.

2. Billy Madison

Year: 1995
Sandler Crew: Sandler and Herlihy on screenplay duties.
SNL buddy count: 2, both old school: Chris Farley and Norm MacDonald.
Love interest: Bridgette Wilson-Sampras, seven years younger.
If Happy Gilmore is a slightly better-formed movie in terms of story, Billy Madison is perhaps a slightly purer expression of Adam Sandler at 29. Yes, he was 29 when Billy Madison came out; that actually seems old to me. I guess that means he was only 24 or so when he started on Saturday Night Live, like similarly youthful Jimmy Fallon, and 29 is a decent fit for the arrested-development character of Billy Madison, a spoiled rich kid whose entire life has been a formless cruise through whatever he feels like doing. But Billy Madison also feels even more youthful, the kind of movie you might expect a twenty-three-year-old to make given enough freedom from executive interference. At the time, I thought of its sensibility as sort of a lower-budget Wayne’s World. That probably reflects the degree to which Wayne’s World loomed over my post-Airplane! sensibilities in cinematic comedy as much as actual commonalities, but there is an element of Sandler picking up the Mike Myers impudent-youngster baton and running it through more flagrantly antisocial territory. And much as Wayne’s World provided a clearer picture of the Mike Myers sensibility, the glimpses of weird brilliance Sandler showed during an uneven tenure on SNL (even given the baseline unevenness of any SNL tenure) had more time to develop — not too much, mind, but enough to eventually make him a star.

Wedding Singer

1. The Wedding Singer

Year: 1998
Sandler Crew: Director Frank Coraci and sole credited screenwriter Tim Herlihy.
SNL buddy count: 3: Kevin Nealon, Robert Smigel, and Jon Lovitz.
Love interest: Barrymore again, but seriously, she’s nine years younger?!
If there’s a genre more typically formulaic than a sports movie, it’s a romantic comedy — and again Sandler works through extremely tired formula with a loopy energy and even charm. His 1985 wedding singer is more lovable hangdog than sociopath (his fits of rage come during his post-breakup performances), and he strikes puppy-dog-style sparks with Drew Barrymore as a sweet girl engaged to the wrong guy. Sandler is a screwball in the broad sense, but his romantic chemistry with Barrymore isn’t screwball in the least: it’s gentle and silly and vaguely teenage. With other stars, that might seem regressive; for Sandler, it makes total sense. Same goes for the generic all-eighties “1985” setting, an early signpost for Sandler’s love of chintzy eighties culture he grew up with (see also: the mostly-terrible soundtracks to most of his movies). While sticking to its rom-com structure (of the friends-who-might-be-something-more variety, rather than the clash-then-swoon version that Blended attempts), The Wedding Singer also finds room for some of Sandler/Herlihy’s best side business: Steve Buscemi’s drunken wedding toast; Jon Lovitz’s strutting wedding-singer competition; even Ellen Dow’s rapping granny routine is pretty cute in context. Many of his comedies play like they’re set in Adam Sandler Fantasyland; The Wedding Singer makes it look like a particularly nice place to visit.