The Iconic Trio: Ranking All 3 Drew Barrymore And Adam Sandler Movies (Plus The Latest On Their Next Film)

The enduring on-screen chemistry between Drew Barrymore and Adam Sandler is one of Hollywood’s most reliable sources of romantic comedy gold. Spanning three decades and three blockbuster films, their partnership has consistently delivered heartwarming, hilarious, and genuinely sweet performances that transcend the typical rom-com formula. As of December 2025, fans are buzzing with excitement, as both stars have recently confirmed their commitment to a long-awaited fourth movie, proving their friendship is as strong as ever.

Their collaborative filmography serves as a nostalgic timeline for a generation of moviegoers, showcasing the evolution of romantic comedy from the 80s-obsessed nostalgia of the late 90s to the family-focused adventures of the 2010s. This article dives deep into the iconic trio of films that define their cinematic partnership, offering fresh details on their box office success, unique production stories, and the latest updates on their potential next project.

A Partnership Forged in Comedy: The Complete Filmography

The magic of the Drew Barrymore and Adam Sandler pairing lies in their authentic, platonic friendship, which translates into believable and charming on-screen romance. Barrymore herself once called Sandler her "best on-screen kiss," emphasizing that their connection "is representing something bigger than hot, sexual chemistry." Their success is not just a fluke; it's a deliberate, decades-long collaboration.

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Here is the complete list of their co-starring feature films, ranked by their cultural impact and critical reception:

1. The Wedding Singer (1998): The Perfect Harmony

Released in 1998, The Wedding Singer was the film that started it all, not only launching the Barrymore-Sandler partnership but also pivoting Adam Sandler’s career from raunchy frat-boy humor to a more romantic, yet still goofy, comedic style. The film, directed by Frank Coraci, is a loving homage to the 1980s, complete with big hair, questionable fashion, and a killer soundtrack.

• Sandler’s Role: Robbie Hart, a New Jersey wedding singer jilted at the altar.
• Barrymore’s Role: Julia Sullivan, a sweet waitress who works at the same venue.
• The Plot: Robbie and Julia bond over their disastrous love lives, slowly realizing they are meant for each other.
• Box Office & Reception: Produced on a modest budget of $18 million, the film was a massive commercial success, grossing $123.3 million worldwide. It was also well-received by critics, who praised the genuine chemistry between the leads and the film's unexpected sweetness, distinguishing it from Sandler’s previous work.
• Unique Fact: Drew Barrymore was instrumental in getting Sandler to star in the film. She reportedly sought him out specifically for the role of Robbie Hart after seeing his work, believing their energies would complement each other. Her proactive approach is often credited with kickstarting their entire cinematic legacy.

2. 50 First Dates (2004): The Unforgettable Romance

Six years after their first collaboration, Barrymore and Sandler reunited for 50 First Dates, a high-concept romantic comedy set in the beautiful, sun-drenched landscape of Hawaii. This film solidified their status as a powerhouse duo, combining the emotional stakes of a dramatic premise with Sandler's signature absurdist humor.

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• Sandler’s Role: Henry Roth, a marine veterinarian afraid of commitment.
• Barrymore’s Role: Lucy Whitmore, an art teacher suffering from Goldfield Syndrome, a fictional form of anterograde amnesia that causes her to forget each day.
• The Plot: Henry must find a new, creative way to make Lucy fall in love with him every single day.
• Box Office & Reception: Released strategically on Valentine's Day weekend in 2004, the film was a box office phenomenon. It pulled in an impressive $41 million during its opening weekend and went on to gross an incredible $283 million worldwide, making it one of Sandler’s biggest romantic comedy hits.
• Unique Fact: The famous scene where Henry serenades Lucy with a song was a genuine moment for Barrymore. The actress has revealed that she had never heard the song before the cameras rolled, ensuring her emotional reaction to the heartfelt performance was completely authentic. The film also features a memorable supporting cast, including Rob Schneider and Sean Astin.

3. Blended (2014): The Family Vacation Adventure

The third and most recent collaboration, Blended, arrived a decade after 50 First Dates. This film shifted the dynamic from a traditional romantic comedy to a family-centric adventure, featuring the pair as single parents who, after a disastrous blind date, find themselves stuck together with their respective children on a luxurious family vacation in South Africa.

• Sandler’s Role: Jim Friedman, a widowed father of three daughters.
• Barrymore’s Role: Lauren Reynolds, a divorced mother of two sons.
• The Plot: The two families are forced to co-exist at a lavish African resort, leading to unexpected connections and a slow-burn romance.
• Box Office & Reception: While not reaching the domestic heights of its predecessors, Blended still performed respectably on a global scale, earning $126 million worldwide against a $40 million budget. The film continues Sandler’s tradition of using his movies to travel to exotic locations, with the production filming extensively in Sun City, South Africa.
• Unique Fact: Director Frank Coraci returned for this film, making him the only director to helm all three of the iconic Sandler-Barrymore collaborations. The film also features a cameo by Shaquille O’Neal.

The Enduring Friendship and The Hope for a Fourth Film

The real secret to the trio of films' success—The Wedding Singer, 50 First Dates, and Blended—is the genuine, decades-long friendship between the two stars. Their shared history and mutual respect create an undeniable comfort level that radiates off the screen, making their characters’ romantic journeys feel earned.

In recent years, the question of a fourth movie has become a frequent topic of discussion. Drew Barrymore has been particularly vocal about her desire to reunite with her long-time co-star, stating publicly that she wants to "grow old" with Adam Sandler and that they are "running out of time" to make another film.

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What’s Next for the Iconic Duo?

While no official announcement for a fourth romantic comedy has been made, the door is wide open. The recent updates point to their continued professional closeness:

• The Fourth Rom-Com: Both stars have expressed a strong interest in making a fourth film, with Barrymore confirming her constant communication with Sandler about potential projects. The intention for another collaborative film is clearly there, suggesting it’s a matter of finding the right script.
• The Happy Gilmore 2 Connection: Drew Barrymore has also provided a significant, current update on another major Adam Sandler project: the highly anticipated sequel, Happy Gilmore 2. Barrymore confirmed that the sequel is "in process" after speaking with Sandler, demonstrating their ongoing, behind-the-scenes communication about their respective careers.

This constant professional and personal connection keeps the hope alive for fans of their unique brand of comedy. Whether it’s another high-concept rom-com or a more mature look at their characters’ lives, a fourth collaboration between Drew Barrymore and Adam Sandler would undoubtedly be a major cinematic event, continuing the legacy of one of Hollywood’s most beloved on-screen duos.