When Romance Met ComedyWith When Romance Met Comedy, Caroline Siede examines the history of the rom-com through the years, one happily ever after (or not) at a time.  

Robbie Hart (Adam Sandler) and Julia Sullivan (Drew Barrymore) make each other laugh. That’s a surprisingly rare occurrence in romantic comedies, where the jokes are usually reserved for the audience’s benefit. And it’s not just Barrymore’s guileless cater waiter laughing at the madcap antics of Sandler’s charming wedding singer: When they meet-cute near a dumpster behind a New Jersey banquet hall where Robbie’s helping a drunken teenage wedding guest avoid puking in front of his family, Julia’s the first one to crack a joke that makes Robbie smile. Soon enough, they’re laughing together. It’s a sweet, oddball scene that establishes the qualities The Wedding Singer values most: compassion, empathy, camaraderie, and the ability to find joy in even the most mundane circumstances. (Oh, and the importance of never letting Steve Buscemi give a drunken best man toast.)

After a five-year stint on Saturday Night Live and two puerile comedy hits, with 1995’s Billy Madison and 1996’s Happy Gilmore, the last thing anyone expected was for Adam Sandler to make a romantic comedy. But he did, re-teaming with former NYU roommate and long-time writing partner Tim Herlihy, who had co-written those previous films, as well as much of Sandler’s SNL material. And they brought on another college friend, director Frank Coraci, who would become another go-to Sandler collaborator. Barrymore arranged a meeting with Sandler herself, hoping they could become “a modern weird Hepburn, Tracey old Hollywood couple.” Her involvement inspired Herlihy to give his screenplay a female perspective and make it a genuine two-hander, rather than being just a Sandler vehicle. The result is one of the sweetest rom-coms of the 1990s, and my personal favorite romantic comedy of all time.

On paper, there’s a lot about The Wedding Singer that sounds like Sandler’s usual brand of low-brow humor: rapping old ladies, broad ’80s parodies, and his signature yelled line delivery. In practice, however, those elements are used toward gentler, more romantic aims. Before we hear Robbie’s octogenarian singing student, Rosie (Ellen Albertini Dow), deliver the opening bars of “Rapper’s Delight,” the film pauses for a full minute to let her sweetly warble her way through “Till There Was You” while Robbie watches from the sidelines like a proud dad. If cringe comedy thrives in a world where everyone is mean and awkward, The Wedding Singer is the opposite of that. It’s a comedy in which nearly every character is incredibly nice.

Paradoxically, the key to making the film’s gentle tone work is its broad, gaudy ’80s pastiche. (Although The Wedding Singer is technically set in 1985, it functions more as a tribute to the entire decade than an actual period piece—with a killer compilation soundtrack to match.) The biggest challenge for any romantic comedy is balancing the rom and the com, and too many fall back on heightened, conflict-filled premises that inadvertently undercut the heart of their stories. In The Wedding Singer, the ’80s setting functions as a sort of comedy safety net. With Rubik’s Cube jokes and Flock Of Seagulls haircuts to carry the comedic weight, The Wedding Singer is free to be more grounded and naturalistic, telling a character-based story about a wedding singer who’s dumped at the altar and his genial friendship with a woman who’s set to marry the wrong guy.

While reviews for The Wedding Singer were mixed, the 1998 film was Sandler’s first big box office hit, grossing $80.2 million domestically and $123.3 million worldwide. (That’s more than Billy Madison and Happy Gilmore combined.) Thanks to its run as a cable staple, it’s remained a perennial rom-com favorite ever since. And while The Wedding Singer didn’t entirely change the course of Sandler’s career—his next film, The Waterboy, made even more money—it introduced a new element to his acting repertoire: a sense of fundamental kindness that’s been the key to his standout dramatic performances in films like Punch-Drunk Love and The Meyerowitz Stories.

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More than two decades since the film’s release, Robbie Hart remains a compelling vision of masculinity, in a way that feels instructive without trying to impart a specific moral. Robbie’s great at his job, and the film recognizes that it’s thrilling to watch him work a room and effortlessly smooth over reception mishaps. But The Wedding Singer also frames Robbie’s empathy and compassion as admirable strengths, and treats his knowledge of the wedding industry as an invaluable skill set, not a “girly” trait to be mocked. Particularly in the way he’s been dreaming of his wedding day ever since he was a little kid, Robbie fulfills the earnest romantic archetype that’s usually assigned to the female lead. He’s a bit like Say Anything’s Lloyd Dobler, all grown up.

But unlike rom-coms that balance out an idealistic male protagonist with a cynical female one a lá (500) Days Of Summer, The Wedding Singer pairs Robbie with someone who’s just as earnest and romantic as he is. Eschewing the oil-and-water banter that fuels so many rom-com pairings, Robbie and Julia are completely at ease with one another right from the beginning. Their warm friendship blossoms into love so subtly and gradually that it’s not hard to see why they’re so confused by their feelings. It’s the When Harry Met Sally hangout formula, but even simpler and gentler.

Structurally, the most impressive thing about The Wedding Singer is the way it manages to showcase Sandler’s signature angry outbursts without undercutting the love story or making Julia seem like an idiot for putting up with him. Unlike the Apatowian archetype of an immature man-child who needs to grow up in order to be worthy of his love interest, Robbie’s arc is about returning to the person he was before his breakup sent him reeling. It’s a small but crucial distinction; Julia’s willing to help Robbie through his worst because she’s already seen him at his best. And Robbie’s outbursts are even funnier because they’re contrasted against his otherwise soft-spoken demeanor. Thus you get Sandler’s hilarious performance of Robbie’s angst-ridden, Cure-inspired ballad “Somebody Kill Me Please” coupled with the perfect button of Julia’s incongruously upbeat “I liked it!” (And then a Jon Lovitz non sequitur, because why not.)

Although Robbie’s brief foray into insult comedy at a wedding gig gone wrong plays even harsher today than it did in 1998, The Wedding Singer is mostly a reminder that comedy doesn’t have to be mean-spirited to be funny. Because Rosie doesn’t have the money to afford singing lessons, Robbie lets her pay in homemade meatballs instead. (“They taste so good, it’s like I’m ripping you off, Rosie!”) In one early scene, he’s too polite to refuse, and she’s too eager to take his desire to leave—or her lack of Tupperware—as a deterrent, so she winds up scooping two meatballs directly into his hands. It’s a hilarious image that stems from two kindhearted people doing their best to be nice to each other.

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If The Wedding Singer has a flaw, it’s that it’s a bit too simple at times, like it’s a draft or two away from fully tying up its plot threads and using its supporting characters to their full potential. (A charming 2006 Broadway musical adaptation did a nice job fleshing out the film’s world.) Still, strong performances and that general sense of geniality help carry things along. Christine Taylor is almost unnecessarily great as Julia’s promiscuous cousin, Holly, a character without much to do on the page but who really pops thanks to Taylor’s performance. Elsewhere, there’s a lot to parse in how the film treats Robbie’s Boy George-loving bandmate, George Stitzer (Alexis Arquette, who publicly came out as a trans woman a few years after the film’s release). As with a character like Jack on Will & Grace, the film clearly has a lot of affection for George, even as there’s also a sense that we’re supposed to find the character inherently comical. For what it’s worth, the real Boy George was a big fan of the performance, and when Arquette died in 2016, he shared a lovely tribute and dedicated a performance of “Do You Really Want To Hurt Me” to her.

There’s also something a little overly tidy in the way The Wedding Singer makes Julia’s fiancé, Glenn (Matthew Glave), a completely despicable Wall Street douchebag so we don’t feel bad when she leaves him for Robbie. On the other hand, it’s compelling to see Glenn’s toxic masculinity contrasted with Robbie’s non-toxic form, especially in a scene where Robbie adopts Glenn’s misogynistic language in order to suss out that he’s cheating on Julia. (The film doesn’t make this connection itself, but the scene speaks to the unique access men have to challenge misogyny in all-male spaces.) Plenty of rom-com male love interests are nice or charismatic, but Robbie is a genuine emotional caretaker—not just in a romantic context and long before he meets Julia. It’s lovely to see that championed over the surface stability but toxicity Glenn personifies.

And anyway, the real threat of the film isn’t Glenn. It’s the sunk cost fallacy that inspires people to marry someone who isn’t right for them just because they’ve been together so long that it seems like they should. Robbie and Julia’s love story isn’t about destiny or sweeping love-at-first-sight fairy tales. Underneath the ’80s set dressing, it’s about two people who almost settled for the wrong people before realizing there was someone better suited for them out there. So even though the film’s climax involves Billy Idol, hilariously playing a younger version of himself, and leading his fellow first-class passengers on a charge against Glenn, the lyrics of Robbie’s airplane serenade “Grow Old With You” are filled with images of what love actually looks like: doing the dishes, taking care of someone when they’re sick, and even giving up the remote control.

It’s one of the best climaxes in romantic comedy history—the perfect cathartic culmination of all the good will Sandler has built up with his openhearted performance and all the emotional heft Barrymore brings to the film. As sweet as the song is, the scene wouldn’t work without the overwhelming sense of joy and relief Barrymore brings to Julia’s reaction. Although Sandler and Barrymore’s rom-com reunions, in 50 First Dates and Blended, offered diminishing returns, it’s not hard to see why they were pulled to try to recapture the magic.

Romantic comedies often sell the fantasy of “having it all,” meaning both the great partner and the great career. The Wedding Singer, meanwhile, challenges conventional ideas of what “having it all” looks like. It argues you don’t need to be professionally ambitious to have a fulfilling life—which isn’t something Americans are used to hearing, even outside of the “greed is good” ethos of the 1980s. The Wedding Singer suggests that “having it all” can mean surrounding yourself with people you love, doing good deeds for others, and finding a job that fulfills you, even if it doesn’t pay much and it’s vaguely uncool.

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In other words, the ultimate fantasy of The Wedding Singer is how nice it would be to live in the New Jersey suburbs with someone who lets you have the window seat when you’re flying over a pretty view. It’s the sort of idea some mistakenly think defines the romantic comedy genre, but it actually doesn’t—at least not in such a beautifully simple way and with such a radically gentle male protagonist. The Wedding Singer might look like a bawdy Adam Sandler salute to the ’80s, but its kindhearted worldview makes it a timeless and unique romance.

Next time: The Philadelphia Story delivered an old Hollywood team-up for the ages.