Before signing on for Happy Gilmore 2, Haley Joel Osment was a part of Silicon Valley, which currently boasts a 94% Rotten Tomatoes score. Here, he played the role of Keenan Feldspar, a weird but brilliant VR developer, and brought laughs to the show’s already wild tech world. Even in the short arc of three episodes, he didn’t miss his comedic timing at all.
And here’s the thing: his performance elevated the show to a great level. So, if you’ve missed out on this gold, make sure to add this to your watch list. Let’s dive deeper and know more about the show and Osment’s impressive role.
The sitcom genre can easily be one of the toughest to crack. While we all loved the laughter-filled madness of FRIENDS and The Big Bang Theory, Haley Joel Osment’s Silicon Valley is also right up our alley. It can also easily be one of the smartest shows ever made about the tech world.
Created by Mike Judge, who worked in tech himself, the series takes a funny yet honest look at the startup culture and life, and all the chaos that comes with it. Sounds amazing, right? Across its six-season run, the show earned huge praise from critics and fans alike. The Rotten Tomatoes scores also often hit above 90 percent, and it has a good 84 Metacritic score.
Fans loved the fast and sharp writing, as well as how the series poked fun at tech culture while still feeling real. Not only this, but it also highlighted the other side of the culture, such as pressure, ego, and weirdness as well. The premise is definitely a highlight, but the great ensemble, on the other hand, made it all happen with ease.
Richard Hendricks, the awkward genius behind the main startup, was joined by standouts like Gilfoyle and Dinesh, two characters whose hilarious bangers became a fan-favorite. In the end, Silicon Valley nailed the perfect balance of comedy and real-world critique, earning its spot as one of the best tech comedies ever made.
Adam Sandler and Bad Bunny in a still from Happy Gilmore 2 | Credits: Netflix
Haley Joel Osment appears in Happy Gilmore 2 as Billy Jenkins, a character who stands in clear contrast to Adam Sandler’s Happy. Jenkins stands for a modern version of golf – refined, media-savvy, and fronting the newly launched “Maxi Golf League” backed by Frank Manatee. The actor plays him with precision, offering a sharp opponent who pushes Happy both on and off the course.
Set nearly thirty years after the first movie, the sequel follows Happy as he returns to golf with a personal mission. He’s trying to raise funds for his daughter’s ballet school following a loss in the family. Jenkins isn’t just another rival. He’s the face of how the game has changed, mixing business strategy with clean technique.
Osment is at the core of the film’s major tournament scenes, where Jenkins’ calculated, sponsor-backed presence goes up against Happy’s more instinctive play. The tension between them is about more than just winning. It taps into larger ideas around generational shifts and the difference between substance and spectacle. Osment keeps Jenkins grounded, and the movie brings back familiar characters across sports and entertainment.
Osment’s past roles, particularly as Keenan Feldspar in Silicon Valley, make his casting feel intentional. He has a track record of playing characters who balance composure with pressure, and that same edge is what gives Billy Jenkins a real presence in Happy Gilmore 2.
Have you watched Haley Joel Osment in Silicon Valley? Let us know in the comments below.
You can currently watch Silicon Valley in the USA on HBO Max. Meanwhile, Happy Gilmore 2 can be streamed on Netflix.
