The Ultimate Guide To Happy Gilmore 2 Cameos: 15+ Shocking Appearances You Missed!

The highly-anticipated sequel, Happy Gilmore 2, has finally landed on Netflix, and as of today, December 10, 2025, fans are already buzzing about the sheer volume of star-studded cameo appearances. Adam Sandler, a master of the celebrity drop-in, has outdone himself, packing the film with over 40 recognizable faces, from music icons and sports legends to his beloved former co-stars and family members. The film, which sees Happy Gilmore come out of retirement, is a non-stop parade of shocking and hilarious guest spots that serve as a love letter to both the original movie and Sandler’s extensive network.

The sequel, which filmed extensively in New Jersey, reportedly generated a massive $152 million spend during its 64 days of production, a testament to the scale of this comedic undertaking. The cameos aren't just one-off gags; many are woven directly into the plot, creating a rich tapestry of callbacks and new comedic gold. Here is the definitive breakdown of the most surprising and essential cameos in Happy Gilmore 2.

The Return of the Originals: Beloved Characters Who Came Back

No Happy Gilmore sequel would be complete without the return of the characters who made the original a classic. While the story brings Happy out of retirement, it also brings back his greatest nemesis and a few fan-favorite supporting players, much to the delight of the audience.

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• Christopher McDonald as Shooter McGavin: The iconic antagonist is back to challenge Happy's return to the links. McDonald’s reprisal of the role was one of the most celebrated announcements of the sequel's production.
• Ben Stiller as Hal: The abusive nursing home orderly, Hal, is back in a cameo that is as uncomfortable as it is hilarious. Stiller's return was a must-have for longtime fans of the original film.
• Jon Lovitz: While his original character, the golf tour's public relations director, is not explicitly named in every report, Lovitz makes an appearance that fans will instantly recognize, bringing his signature comedic energy.
• Blake Clark: Another familiar face from the Sandler universe, Clark also makes an appearance, continuing his long-standing collaboration with the star.
• Julie Bowen as Virginia Venit Gilmore: The plot features a significant, albeit sad, twist: Happy's wife, Virginia Venit Gilmore, is listed as deceased, which serves as a major catalyst for Happy’s return to golf. Despite this, Julie Bowen is credited in the cast, suggesting she appears in flashbacks or a spiritual role.

Music Icons and A-List Celebrities That Stole the Show

Adam Sandler's films are notorious for featuring unexpected celebrity appearances, but Happy Gilmore 2 takes this tradition to a new level. The sequel is peppered with major names from the music, sports, and culinary worlds, often playing exaggerated versions of themselves or taking on bizarre new roles.

Bad Bunny as Oscar, Happy’s Caddie

One of the most significant new additions to the cast is Puerto Rican superstar Benito Antonio Martínez Ocasio, better known as Bad Bunny. He takes on the role of Oscar, Happy Gilmore's new caddie. His presence is a major feature of the film, providing a fresh dynamic to Happy’s journey and bridging the gap between generations of fans. This is not a blink-and-you-miss-it moment, but a substantial supporting role, showcasing Sandler's commitment to current pop culture relevancy.

Eminem as Donald Jr.

In a truly shocking and unexpected twist, rap legend Eminem (Marshall Mathers) makes a cameo appearance as a character named Donald Jr. This cameo is generating significant buzz, not only for the rapper's rare comedic role but also for the specific character he portrays, adding a layer of meta-commentary to the film's humor. The interaction between Eminem and Sandler is a highlight for many viewers.

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Eric André and Kid Cudi

The film features appearances from two more comedic and musical talents. Eric André is credited as playing a character named Steiner, while Kid Cudi (Scott Mescudi) appears as an FBI Agent. These roles demonstrate Sandler's strategy of bringing in contemporary comedians and artists known for their surreal and off-kilter humor, perfectly fitting the zany world of Happy Gilmore.

The Sandler Family and Friends Universe

It wouldn't be an Adam Sandler production without appearances from his inner circle, including his family and frequent collaborators. These roles often feel like a fun nod to the audience, reinforcing the tight-knit "Sandlerverse."

• Steve Buscemi: The legendary actor and longtime friend of Sandler appears as Happy's offbeat new neighbor. Buscemi's presence adds a familiar, quirky element to the film's domestic scenes.
• Jackie Sandler: Adam’s wife, Jackie Sandler, makes a cameo as Monica, Vienna's dance instructor.
• Sadie Sandler and Sunny Sandler: Adam and Jackie's daughters, Sadie and Sunny Sandler, also continue their tradition of appearing in their father's films, taking on roles that further cement the family's involvement in the production.
• Haley Joel Osment: Known for his dramatic roles, Osment makes a surprising appearance, showcasing his comedic timing alongside the Sandler crew.
• Guy Fieri: The 'Mayor of Flavortown' himself, Guy Fieri, appears in a memorable spot, bringing his unique, high-energy persona to the golf comedy.
• Ken: A mysterious and fun cameo from an actor named Ken is also noted among the extensive list of guest stars.

Golf Legends and Sports Stars

The original Happy Gilmore featured appearances from golf icons like Lee Trevino. The sequel continues this tradition, inviting some of the biggest names in golf history to participate in the chaos, most notably during a pivotal Tour Champions dinner scene.

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• Fred Couples: The former Masters champion and World Golf Hall of Famer makes an appearance.
• Nick Faldo: The six-time major champion and renowned commentator is another golf legend who joins the fun.
• Jack Nicklaus: Considered by many to be the greatest golfer of all time, the "Golden Bear" himself is featured.
• Corey Pavin: The former U.S. Open champion is also among the sports stars making a cameo.
• Lee Trevino: In a wonderful nod to the original film, Lee Trevino returns, reprising his role and delighting longtime fans with his presence.
• Reggie Bush: The former Heisman Trophy winner and NFL star makes a surprising appearance as a character named 8 Ball.

The sheer volume and star power of the Happy Gilmore 2 cameos are a clear indication of Adam Sandler’s influence in Hollywood and the cultural impact of the original film. From the return of classic characters like Shooter McGavin to the unexpected inclusion of Bad Bunny, Eminem, and a roster of golf legends, the sequel delivers on its promise of a star-studded, laugh-out-loud comedy. These appearances are not just fleeting moments; they are integral parts of the film's structure, providing both nostalgic comfort and fresh, modern humor for a new generation of fans.