Nearly two decades later, Happy Gilmore continues to be one of Happy Gilmore 2 will be a first for the writer, director, and actor. Even though Happy Gilmore has yet to receive an official announcement, the film is at least in development. Although Happy Gilmore is full of plenty of laughs, as well as some tender and emotional moments, its greatest strength is its characters, many of whom deserve to return in the sequel.

Of course, Happy Gilmore 2 is bound to feature a partially new cast of characters, considering that some of its predecessor's cast have ed away. s Bay (Granda Gilmore), Carl Weathers (Derick "Chubbs" Peterson), and Richard Kiel (Mr. Larson) died in 2011, 2024, and 2014 respectively. But while bringing back the original cast in its entirety is impossible, seeing a handful of the first movie's characters reprise their roles is a real possibility for the sequel.

4 Julie Bowen As Virginia Venit

Happy Gilmore's True Love

Virginia Venit (Julie Bowen) is Happy's primary romantic interest in Happy Gilmore and a huge part of his character development. When Happy first meets Virginia, he has anger issues and is very stubborn in his way of thinking, but in the end, Virginia brings out his soft side. However, she is also strict with him and wouldn't accept his behavior, which helps him realize exactly what his priorities are. Plus, Grandma Gilmore (s Bay) loves her, which is a huge bonus. Unfortunately, Bay ed away in 2011, so Happy's grandmother won't return for Happy Gilmore 2.

Virginia also undergoes some changes in Happy Gilmore. Initially, Virginia is the publicist for the golf tournaments who focuses on her career more than anything else. Meeting Happy allows Virginia to relax more and enjoy the sport outside of her job. Because of her bond with Happy, she eventually breaks her rule of not dating golfers to be with him, much to Shooter's dismay. If Happy Gilmore 2 happens, their relationship will surely be a hot topic in the film's plot.

Since starring in Happy Gilmore, Bowen's biggest role is as Claire Dunphy in Modern Family, making her an even more prominent figure in Hollywood. Therefore, it will make sense if Sandler brings her back for the sequel. Bowen's decorated career is a desirable quality for the Happy Gilmore 2 cast, but Virginia is also an essential character in Happy's story, and it would be rather strange if she were absent in the sequel. Although Happy Gilmore 2's story is yet to be revealed, it seems more than likely that Virginia will appear, even if she and Happy aren't together anymore.

3 Christoper McDonald As Shooter McGavin

The Greatest Rival Of Happy Gilmore's

Christopher McDonald's Shooter McGavin is introduced as the primary villain of Happy Gilmore through his persistent attempts to try and sabotage Happy. For example, at one point, Shooter hires a man named Donald (Joe Flaherty) to constantly harass Happy while he plays in an attempt to distract him. Shooter also purchases Grandma Gilmore's house to manipulate Happy, only for him to lose it to him in a bet at the end of the film. While a generally irritating antagonist, Shooter also has some funny moments, especially his frustrated outbursts over being outshone by Happy.

Since Sandler's tease about Happy Gilmore 2, Christopher McDonald has been very vocal on social media about the possible project. Interestingly, Shooter McGavin appears to be the favorite of the characters McDonald portrays and even appears on X under the character's name. He's shared multiple jokes about Adam Sandler, all in good fun, which implies that the actor is keen to reprise his role as Shooter McGavin. Even Adam Sandler is making jokes about McDonald's excitement, which he discussed with Dan Patrick in his webseries The Dan Patrick Show.

What's more, a possible Happy Gilmore 2 would be difficult to realize without McDonald's involvement. The character is easy to root against while being enjoyable enough that audiences want to see more. At the end of Happy Gilmore, Shooter is an embarrassment, filled with rage, and his career in tatters, all because he loses to Happy. Shooter's ending opens up several brilliant storylines that Happy Gilmore 2 can use. For example, Shooter plotting his revenge on Happy nearly 20 years later or a situation with the pair having to work together are two interesting ways Sandler's new film can reintroduce the character.

2 Allen Covert As Otto

Happy Gilmore's Caddy Turned Best Friend

In Happy Gilmore, the titular character meets Otto (Allen Covert), a homeless man who becomes his caddy. Their first interaction occurs as Happy arrives for a tournament, and Otto tries to wash his car but is taken away by security. This moment with Otto highlights how understanding Happy is, especially in a life with money struggles, and immediately defends a stranger who is down on his luck, even giving the man his last dollar and later hiring him as his caddy, thus setting up a great character dynamic between the two.

Otto is one of the most underrated characters in Happy Gilmore and provides some very funny moments throughout. For example, at one point, he rather casually takes a shower in the golf course pond, either unaware or simply not caring about anyone spotting him. Another great moment of Otto's is when he tries to help plan out a shot with Happy. However, Otto thinks they are on uneven ground, only for Happy to tell him that "it only seems that way because [he has] only one shoe on," which is easily one of Happy Gilmore's subtly funny moments.

Interestingly, the character's name isn't uttered on-screen at any point. But in a deleted scene, it is revealed to be Otto. However, Covert is fully credited as Otto, unlike some other big names in the film. Happy Gilmore isn't Allen Covert's only Sandler film, though. The actor also stars in titles such as I Now Pronounce You Chuck and Larry and Big Daddy, as Covert and Sandler are friends and have been for many years. Because of these factors, it seems likely that Otto will return for Happy Gilmore 2, hopefully as a changed man with Happy's help.

1 Ben Stiller As Hal

The Abusive Retirement Home Worker In Happy Gilmore

Hal (Ben Stiller) has a very minor role in Happy Gilmore but is still a great character overall. The sadistic retirement home manager has some great scenes in the film, albeit few. For example, when Happy drops his Grandma off, Hal initially seems to be sweet and ive, but as soon as the door closes, his personality shifts. In secret, Hal runs a sweatshop and uses the elderly residents to knit blankets that he then sells for an extortionate price, and when one complains, he sends them outside for landscaping duty instead.

Interestingly, neither the character nor Stiller appears in the credits of Happy Gilmore. Even still, Hal makes an incredible impact in the brief appearances he makes throughout Happy Gilmore. Stiller also reprises his role in Sandler's 2020 film Hubie Halloween, so despite being a nominal character, it proves that his use of humor as Hal is still as appreciated so many years later. Stiller also appears in other movies with Adam Sandler, such as The Meyerowitz Stories, where the two play Matthew and Danny Meyerowitz, respectively.

Happy Gilmore 2 is a great opportunity for Sandler to expand on Stiller's character. Although there has been no hint in Happy Gilmore 2's story so far, this means that the ways Hal can be interwoven in the story are endless. Hal's ridiculous schemes and sketchy ways, which is what makes him such an enjoyable character anyway, means that the character can be anywhere, doing anything. Perhaps Happy will finally get his revenge for how Hal treats his Grandma, or in a nod to the running joke in Happy Gilmore, he could be a Subway sandwich artist.