Who is Billy Jenkins? Meet the actor playing the new character in Happy Gilmore 2

Happy Gilmore 2 premiered on Netflix on July 25, 2025, almost 30 years after the original 1996 hit. Directed by Kyle Newacheck and written by Adam Sandler and Tim Herlihy, the film follows Gilmore (Sandler) as he returns to golf to raise money for his daughter’s ballet school.

The sequel brings back familiar faces and is filled with nostalgic moments, along with surprise cameos from famous artists, athletes, and longtime Sandler collaborators.

With a sequel full of nostalgia and celebrity cameos, one of the standout new characters is Billy Jenkins, portrayed by Haley Joel Osment. Yes, Osment officially joins the franchise in a significant role, adding to the classic tale while serving as Happy’s principal rival.

---

Haley Joel Osment as Billy Jenkins in Happy Gilmore 2

Cinespia 20th Anniversary Screening Of "The Sixth Sense" Presented By Amazon Studios - Source: Getty

Osment, whose Oscar-nominated debut with The Sixth Sense (1999) remains a major highlight of his career, plays Billy Jenkins, a polished antagonist in Frank Manatee’s extravagant “Maxi Golf League.”

Osment plays a vital role in several important scenes, particularly at major tournaments in which Happy competes against the league of Manatee. Jenkins is portrayed as disciplined, media-trained, and surgically enhanced to represent the corporate, modern look of the league.

He contributes as Happy’s main foil, representing both the personal arc of recovery and the spectacle of performance golf.

---

What is Happy Gilmore 2 about?

Happy Gilmore 2 is a film featuring Adam Sandler as Happy Gilmore, who re-joins the golf fraternity to pay for his daughter Vienna’s (Sunny Sandler) ballet school tuition after his wife Virginia (Julie Bowen) dies in a tragic accident.

Trying to overcome a loss, the lack of money, and alcohol recovery, Happy attempts to redeem himself in the sport in which he was a champion. The central rivalry develops when billionaire Frank Manatee (Benny Safdie) opens a flashy counter-competition, the Maxi Golf League.

The competition includes upgraded corporate-sponsored players such as Billy Jenkins (Haley Joel Osment), who serves as Happy’s primary adversary. In addition to this new contest, the movie also reunites favorite characters such as Shooter McGavin (Christopher McDonald), Hal L. (Ben Stiller), and Gary Potter (Kevin Nealon).

These returns are further boosted by approximately 50 celebrity cameos from across the worlds of golfing, music, sports broadcasting, and social media industries, transforming the movie into a proper celebration of the Sandler cinematic universe and his comedic legacy.

---

Happy Gilmore 2 cameos: here’s who appears

Happy Gilmore 2 delivers a mix of cameos, blending Hollywood, sports, and pop culture into a nostalgia-fueled spectacle. Haley Joel Osment, playing Billy Jenkins, serves as the centerpiece of redemption, while the surrounding cast of guest appearances adds star power across multiple arenas.

Happy Gilmore 2 World Premiere - Source: Getty

Music & Pop Culture

• Bad Bunny
• Post Malone
• Eminem
• Kid Cudi

Supporting performances in smaller but noteworthy turns are by Cam’ron, Andrew Watt, and Eric André, each playing offbeat roles that add punch to transitional scenes.

Golfing

Numerous self-referencing cameos by golf legends lead to a sense of reality in the tournament sequences of the movie:

• Jack Nicklaus
• Tiger Woods
• Rory McIlroy
• Brooks Koepka
• Bryson DeChambeau
• Scottie Scheffler
• Jordan Spieth
• Collin Morikawa
• Will Zalatoris
• Tony Finau
• Rickie Fowler
• Fred Couples
• Lee Trevino
• Nancy Lopez
• Paige Spiranac
• Keegan Bradley
• Corey Pavin
• Bubba Watson

And more are spotted between match sequences in the Maxi Golf League.

Sports World Cameos

• Travis Kelce
• Reggie Bush
• Becky Lynch
• Nikki Garcia (Nikki Bella)
• Kelsey Plum
• Boban Marjanović

Media & internet personalities

• Dan Patrick
• Stephen A. Smith
• Chris Berman
• Ken Jennings
• Verne Lundquist
• Alix Earle
• Sean Evans

---

Happy Gilmore 2 will premiere as a Netflix exclusive on July 25, 2025, bringing back a classic franchise with a new lineup of characters and major cameos.

Edited by Divya Singh