How The Wedding Singer Changed Adam Sandler’s Career

By the time The Wedding Singer came out in 1998, Adam Sandler and Drew Barrymore were both known for very different reasons. Sandler was a breakout star from Saturday Night Live, fresh off the success of his broad 1990s comedies Billy Madison and Happy Gilmore, while Barrymore was a former troubled child star in the midst of a career renaissance. They didn’t seem like a natural pairing, Sandler’s brusque comedic stylings a jarring contrast with Barrymore’s warmer tones. But they work well together in The Wedding Singer, and the film serves as not only a springboard for them as a popular romantic pairing, but lays the groundwork for Adam Sandler’s future career in more independent dramatic fare.

By the time Adam Sandler took on the role of Robbie Hart in The Wedding Singer, he hadn’t exactly demonstrated tremendous range as an actor. Most of his roles were of the shouty variety, involving Sandler playing a manchild who is caught up in some outlandish comedy scenario. In Billy Madison, he plays the heir to a hotel fortune who has to go back to school (starting with elementary school) in order to claim his inheritance, while Happy Gilmore sees him as a failed amateur hockey player with rage issues who embarks upon a career as a golfer upon discovering a natural affinity for the sport. His character in The Wedding Singer, by contrast, is much more grounded in reality. Robbie Hart is a wedding singer in New Jersey who is crushed when his fiance leaves him at the altar, leaving him heartbroken and forced to help plan the wedding of his coworker, whom he’s beginning to develop feelings for. He still gets a few of his shouty moments in – Robbie returns to sing at a wedding mere days after his own failed nuptials, and essentially has a breakdown in real time on stage – but for the most part, he’s a gentle, even-tempered man. 

As a wedding singer, he has a responsibility of keeping the evening running smoothly so, in a rare move for Sandler, he’s the calm center of the storm as chaos swirls around him. In spite of this, there’s a darkness to Robbie, a caustic sense of humor he displays on occasion (like when he cheerfully tells an acquaintance to have a few drinks and then, you know, drive home) and a deep reserve of anguish (his Cure-inspired love song to Linda, for example). This allows him to demonstrate a different aspect of his comedic persona that paves the way for the darker comedies and independent dramas – Punch Drunk Love and Uncut Gems chief among them – that have won him so much critical acclaim.


The Wedding Singer also establishes Sandler as a viable romantic lead for the first time in his career. His previous films all featured a romantic element – the hero has to get the girl, after all. But these were always executed fairly childishly and were never the point of the film; Happy Gilmore and Billy Madison would both function perfectly well without a love interest. The winning chemistry between Barrymore and Sandler proves that the actor had a few more tricks up his sleeve, and the two went on to star together in two other romantic comedies, 2004’s 50 First Dates and 2014’s Blended. But aside from their films together, The Wedding Singer opened up a door for Adam Sandler to branch out into rom-coms in general. In the years that followed, he still did a number of straight comedies, but he also found increasing success as a romantic lead, starring opposite actresses such as Jennifer Aniston and Paz Vega.

The Wedding Singer is not often listed among the best Adam Sandler films – people tend to prefer the ones that are more overtly comedic, or the independent dramas that are more artistically inclined. But aside from being a simple yet charming romantic comedy, The Wedding Singer deserves credit for being the first film to give audiences a glimpse of the bizarrely varied career ahead of him. Before this, it would be difficult to imagine him starring in edgy dramatic films that were legitimate awards contenders. This is the guy who made bottles of shampoo and conditioner fight with each other while taking a bubble bath in Billy Madison, after all, and it’s not easy to take such a massive leap once people are used to seeing you as a clown. But if nothing else, The Wedding Singer, with all its humble charms, presented viewers with the idea that Adam Sandler might have more to him than just childish on-screen tantrums and gross-out humor. He doesn’t always – sometimes he’s more than happy to fall back on the goofy comedy that made him famous – but every once in a while he’s capable of surprising audiences.

“The Wedding Singer” is now streaming on HBO Max.

Audrey Fox is a Boston-based film critic whose work has appeared at Nerdist, Awards Circuit, We Live Entertainment, and We Are the Mutants, amongst others. She is an assistant editor at Jumpcut Online, where she also serves as co-host of the Jumpcast podcast. Audrey has been blessed by our film tomato overlords with their official seal of approval.

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