Winona Ryder costars in a Frank Capra remake, which stuffs celebrity cameos and standing-ovation populism into a billion-dollar inheritance farce.

Every week, Entertainment Weekly is looking back at the biggest movies of the summer of 2002. As audiences struggled to understand the new post-9/11 world order, Hollywood found itself in a moment of transition, with upcoming stars and soon-to-be-forever franchises playing alongside startling new visions and fading remnants of the old normal. Join us for a rewatch of the first true summer of Hollywood's strange new millennium. Last week: Patrick Gomez and Christian Holub took an emotional island vacation with Lilo & Stitch. This week: Leah Greenblatt and Darren Franich go to town with Mr. Deeds. Next week: Here come the men in black…again.

Credit: Everett Collection

DARREN: Was this the most precarious moment in Adam Sandler's career? The former Saturday Night Live star flew high out of the '90s. From the wide view of history, it's been gravy ever since: a string of hits for Columbia, a paradigm shift to Netflix when the comedy box office dried up, and now a recent midlife turn to career-best work for directors like Noah Baumbach and the Safdie brothers. It could have gone another way. Little Nicky was a genuine flop in 2000. Mr. Deeds arrived in theaters just a month after the Cannes opening of Punch-Drunk Love, a now-sacred classic that wouldn't even earn back its modest $25 million budget. Of course, by the time Punch-Drunk hit theaters, Mr. Deeds had already made $171 million globally. But I sensed some simmering anxiety on this rewatch, a back-to-basics retrenchment to safe blandness that would define Sandler's upcoming decade.

He plays Longfellow Deeds, a super nice guy beloved by everyone who inherits $40 billion from a surprise-tycoon great-uncle. The concept comes loosely from a Frank Capra movie, but Deeds is a pure shot of Sandler cinema. There's the nonstop product placement. See the plane stopover at Wendy's, and Sandler himself mouthing the immortal line: "I'm so happy I got the Big Bacon Classic!" There's the celebrity cameo (John McEnroe, high-jumping over a moving car) and the tiny parts for Steve Buscemi and Rob Schneider. And there are so many people giving Deeds a standing ovation. His small town of Mandrake Falls cheers for him as he leaves for New York City. New Yorkers cheer for him when he saves a woman and seven (seven!) cats from a burning building. Shareholders cheer for Deeds when he convinces them to put people above profits, and then they cheer for him again a little later.

Are you catching the frantic urge to be liked? Don't overlook the paranoia, either: Sandler was already notoriously press-shy by 2002, and in Deeds, the media itself is the villain, embodied by vain TV host Mac MacGrath (Jared Harris) and a New Yorker staffer so jerky that it's a hero moment when Deeds pummels him. And then there's Babe Bennett (Winona Ryder), a duplicitous reporter who cozies up to the main character under false pretenses — and falls for his small-town charms. I kinda like Ryder, even if her character (literally, you'll recall, named "Babe") is paint-by-numbers. Gotta admit, Deeds gave me a bigger nostalgia hit than any movie we've watched this summer, if only because the soundtrack captures the accurate mood of a hip 2002 elevator ride.

Leah, did you love Mr. Deeds as much as everyone in Mr. Deeds did? 

LEAH: I am like Nell in the woods on this one, chickapay; I was not a Sandler girl back in 2002, so Deeds completely missed me. His whole Happy-Billy-Waterboy era honestly just felt like a dog whistle I couldn't hear, or one of those fake trailers in Tropic Thunder (and if we're playing that game, I'd rather see how Satan's Alley turns out). Besides 1998's The Wedding Singer, which I still love, it seemed like he was mostly making movies for boys, or at least the junior high at heart, until stuff like Spanglish and 50 First Dates came along. But watching the movie for the first time this week, I could see hints of the more interesting actor he'd become — one that would eventually have me sincerely saying the words, "This man has been robbed of an Oscar nomination." (Justice for Gems!)

Don't get me wrong, I think Deeds is still pretty dumb, and not very far from that whole run of arrested-development rage-aholics, dipsticks, and sports clowns that made him a star. But Longfellow is also the kind of holy fool you can root for: just a humble New Englander who writes his own greeting cards, adores his hometown, and breezily gives his $40 billion fortune away to the Negro College Fund. Whether that all sprung from Sandler being at career crossroads, as you say, and craving affirmation, or if it was just his lovable-shlub take on Gary Cooper, I'm not qualified to know — though it is true that Deeds doesn't have any discernible flaws, beyond the frostbitten foot. (Not to get too Dr. Quinn Medicine Woman, but if it's truly dead and black wouldn't it just…fall off?)

As a Winona forever fan, I think she's pretty drastically miscast in this; chemistry test with Sandler aside, which I'd give about a C–, it just feels wrong to sand off all her edges and try to turn her into some honey-blond rom-com queen. She was having a serious career dip too, though Deeds was filmed before her now-infamous 2001 arrest for shoplifting: Post Girl Interrupted, there was a lot of multiplex dreck like Autumn in New York, S1m0ne, and Lost Souls coming through. So there were worse things, maybe, than being asked to play a grown human woman named Babe — which to be fair, was also the name of Jean Arthur's character in the 1936 original — even after it felt like a certain talking pig really claimed that title in 1995. (Side note: this is also, improbably, not the only Ryder movie moment where a girl fall through an ice hole.)

Anyway, Peter Gallagher shows up to do his best Businessman Villain, and his eyebrows have never looked more gloriously minky; he even literally gets a mustache to twirl. John Turturro playing the Spanish butler who's pervy for feet is not something that would pass the Hollywood smell test today, and probably shouldn't, though it's still one of my favorite full-weirdo turns from him since The Big Lebowski. ("Very, very sneaky.") And I'm with you on that 2002 soundtrack: Oh, the Weezer and Natalie Imbruglia of it all! I so want to be a fly in the room when they had to pitch David Bowie to approve the rights for "Space Oddity." I'm curious, though, Darren, since you're much more of an early-Sandler scholar than I am: Do you sense any real pivot in his acting here, or a hint of Howard Ratners to come?

Credit: Everett Collection

DARREN: As a onetime teenage doofus who had entire junior-high conversations quoting Billy Madison's penguin scenes back and forth, I am prepared be our default Sandler scholar. And I think you're right to tease out some granular evolution in his performance style here. Deeds is a genial character who only brutally beats up four people. His most abiding ambition is to write a greeting card. Even that feels like embedded product placement for Hallmark — trust Sandler not to miss a trick — but all the nice-guy poetry is certainly a tone shift from an onscreen history of football, '80s rock, and hockey-golf. "Maybe my poems aren't so great," Deeds tells a table of snobs, "But I know some people who like them. Anyway, it's the best I can do." For a second, you can spot all the sad frustration of Punch-Drunk Love or The Meyerowitz Stories.

And then Deeds punches an opera singer, a Guggenheim board member, and the aforementioned New Yorker writer (take that, elites). There's some core concept here of a small-town fellow getting eaten alive by predatory Manhattanites. "He's a goodhearted guy who we think is a weirdo because he doesn't share our sense of ironic detachment," says Babe — a line which seems a bit tragic coming from Ryder, the patron saint of Gen-X ironic detachment.

Times were changing. You sense shifting mission statements. It's sort of a movie about the sweet country mouse gone to the scary big city — but a couple lines reach for all-in-this-together uplift. "It's an honor to come to the greatest city in the world!" yells Deeds, who will later tell some firefighters that "It's an honor to work with New York's bravest, guys!" Both those honors feel like late ADR additions — and a preview of 2003's Anger Management, which climaxes in Yankees Stadium, when Sandler's final romantic gesture is rescued by beloved All-American Mayor Rudy Giuliani.

Bit of a horror movie in retrospect, but that was the 2000s, a decade Sandler dominated financially. Actually, I think Deeds is more seminal for the actor as a producer. His Happy Madison shingle had previously developed movies for his SNL pals (like Deuce Bigalow and Joe Dirt), plus the aforementioned Little NickyDeeds was the profit multiplier, and it feels like an achievement in moderation, blending the gleeful crassness of Sandler's earlier work with some Big Daddy cutes and so many other things. There are nice old ladies and a joke about belt-whipping child abuse; there's Al Sharpton and some Cocoa Pebbles turned just so toward the camera.

Movie comedy had a real Tower of Babel moment during the last 20 years, with audiences splintering and getting their fix from sitcoms (or, sigh, the internet). I still don't love Deeds, but I do miss the possibility of big-top, big-screen laughs. I dig the loopy tangents — which is also why I have to disagree with you about Ryder. Babe comes up with a quickie childhood backstory about falling off Boo Radley's tree in Winchestertonfieldville, Iowa. This turns out to be a real town, and Deeds flies her there, for a date! Trapped, Ryder does that dancing-hummingbird thing with her eyes, trying hard to maintain her secret identity while also getting exasperated. When a local boy needs medical help, Deeds looks to Babe, an alleged school nurse. "He's choking," Babe says. "We should go." I laughed at Ryder's delivery. I, a parent, laughed at a choking boy.

Were there any individual sequences or lines that worked for you — or really didn't work? And while we're on the topic, Leah, is there a reason why you think Wedding Singer sticks out from the rest of Sandler's early work?

LEAH: Ooh, good question. Drew Barrymore was definitely my gateway drug into that one, but for me it's the human-size scale of it: For once, Sandler wasn't a screaming football savant or the semi-literate son of a hotel millionaire; he wasn't touched by God with a golf swing. He was just a guy whose dreams lived and died on Long Island, a would-be rock star stuck cooing Kajagoogoo to drunk bridesmaids in banquet halls. And I think Adversity Sandler is actually a lot more interesting than the blessed man-child he played for so long. He's still rage-y in Wedding, but the fury is much funnier and more specific to me. (The number of times the phrase "Once again, things that could have been brought to my attention YESTERDAY" still applies in everyday life is truly a self-renewing gift.)

But I digress. I do think it's weird how casually violent Deeds is for a comedy, which is a thing Sandler still seemed to be working out of his system back then. Sure, impale that dead foot on a fire poker! Throw 72 cats out the window, why not! Punch Babe's "mugger" in the face like you're auditioning for Fight Club! I get that it's goofy, but it doesn't really serve the story either, so it's just kind of jarring. (Gary Cooper would never, even in High Noon.) One fun fact I learned in my studies, though (a.k.a. Wikipedia): Sandler's longtime collaborator Tim Herlihy, who wrote the screenplays for this and pretty much all his early films, as well as a bunch of iconic Saturday Night Live sketches, is also the dad of Martin Herlihy, one third of SNL's Please Don't Destroy — which seems like a real study in the evolution of humor on that show, and just generationally.

Look, did I love Deeds? That would be a stretch; like the elevator to Preston Blake's penthouse, it has its ups and downs. But I can say that I enjoyed my education in the Tao of Sandler-dom, and how he got from Winchestertonfieldville to here — "here" being pretty sweet, actually — over the course of the last two decades. Now if you want to meet me at this spot next April to talk about the 20th anniversary of Anger Management and all the ways Jack Nicholson can wear a beret, I will be there with bells on.

Read past 2002 rewatches:

Mr. Deeds
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