Now That ‘Happy Gilmore’ Is Getting a Sequel, Adam Sandler Should Make a Follow-Up to This Rom-Com Movie Next

Adam Sandler doesn’t exactly have the best track record with sequels, as Grown Ups 2, Hotel Transylvania 2, and Murder Mystery 2 were all disappointments that failed to improve upon their predecessors. Although comedy sequels are notoriously difficult to do, there is a significant amount of anticipation for Happy Gilmore 2, as it offers Sandler the opportunity to reprise one of his most famous roles. Sandler’s recent comedic efforts may have been lambasted by critics, but in the 1990s, he was one of the most reliable comedy stars in the industry, as he wasn’t afraid to get very silly and a bit sentimental. Should Happy Gilmore 2 prove to be worth the wait, Sandler has the perfect opportunity to make a sequel to The Wedding Singer.

Sandler gave one of his best performances in The Wedding Singer as Robbie Hart, an idiosyncratic musician who is left devastated after his fiancée Linda (Angela Featherstone) leaves him at the altar based on his lack of success. Although Robbie is now even more miserable having to sing at weddings of other happy couples, he steadily begins to fall in love with Julia (Drew Barrymore), a waitress that works at the same reception hall. The Wedding Singer ends in a way that could leave the door open for a continuation, and might benefit from a modern perspective.

‘The Wedding Singer’ Leaves Room for a Sequel

The Wedding Singer concludes with Robbie and Julia finding love, which is not unusual for a Sandler comedy. Although Sandler’s comedies about married men, such as Grown Ups or Jack & Jill, tend to be among his least successful, a sequel to The Wedding Singer has the opportunity to rectify this, as it has already established why Robbie and Julia are such a perfect couple. Making the sequel would also give Sandler the opportunity to reunite with Barrymore, who has consistently proven to be the best of his female co-stars. It’s often hard for the supporting cast of a Sandler film to stand out, given how much of a scene-stealer he is, but Barrymore is a genuine comedic force of nature, and is certainly deserving of a major comeback.

The Wedding Singer was among the first films to take advantage of nostalgia from the 1980s, as the film is set in 1985 and features music from that decade, despite being released in 1998. Fascination with the films, music, and culture of the ‘80s has grown exponentially in the decades since The Wedding Singer was released, as it has been popularized by It, Stranger Things, and Ready Player One, among others. The Wedding Singer 2 would have several interesting opportunities to address ‘80s nostalgia; while it could make fun of the fact that Robbie is still obsessed with the ‘80s, it could also move the story forward to a different era with its own iconic music. Regardless of its setting, The Wedding Singer 2 would give Sandler the opportunity to do more of his music, which is something that he has always been great at. In recent years, Sandler has earned a lot of acclaim for the original songs he’s performed on his Netflix comedy specials, including a heartfelt tribute to Chris Farley.

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“Oh, you can count. Good for you.”

Robbie Hart Is One of Adam Sandler’s Best Characters

Sandler is always at his best when he’s playing an underdog, and The Wedding Singer sets up the natural next step in Robbie’s journey when he gets the opportunity to share his music with a record company thanks to a favor from Billy Idol, who appears in a hilarious cameo. The exploration of Robbie’s further albums and performances would give The Wedding Singer 2 the opportunity to explore more of the music industry, address modern celebrity culture, and potentially incorporate other appearances by famous musicians. It helps that of all the characters in Sandler’s ‘90s films, Robbie is among the most emotionally intelligent. While it may be hard to deal with the same man-child shenanigans of Billy Madison or The Waterboy in 2025, The Wedding Singer allowed Sandler to play a character who is capable of evolving and becoming a better person.

The Wedding Singer is a legitimately great romantic comedy, and allowed Sandler to combine his inherently hilarious persona with a sincere, sensitive story about outsiders who end up finding love with one another. It was certainly impressive to see that Sandler was capable of giving a more grounded performance in 1998, but in recent years, he’s shown his talent as a dramatic actor in films like Punch-Drunk Love, The Meyerowitz Stories (New and Selected), Uncut Gems, and Hustle, each of which still give him some opportunities to cut the tension with a few well-timed jokes. Even if it doesn’t end up being something in the vein of Before Sunset, a sequel to The Wedding Singer could allow Sandler to capitalize on his improvements as a performer, whilst returning to one of his most beloved roles.