Top 5 Adam Sandler Movie Villains

Love or hate Adam Sandler, it doesn’t matter.  He’s made a number of movies that have combined to earn more than $2 billion at the box office. Sandler himself has an estimated net worth of $420 million and is a solid moneymaker for Netflix, who believes in him so much that they gave him another four-movie deal paying him over $250 million.

I just watched Billy Madison the other day and it still cracks me up, so there’s that. 

But let’s go deeper. His movies rely on a number of things but a memorable antagonist is usually at the top of the list. Let’s take a look at the best of the worst and rank…

Adam Sandler Movie Villains!

Before we jump in I’m going to say that both Bob Barker and Benny Stiller in Happy Gilmore are Hall of Fame and it would be unfair to list them as they would wipe out any and all competition. 

Honorable Mention
Guy Pearce as Kendall Duncan in Bedtime Stories
Angela Featherstone as Linda in The Wedding Singer
Taylor Launter as Andy in Grown Ups 2

TOP 5 Adam Sandler Movie Villains

5. Jerry Reed as Coach Red Beaulieu in The Waterboy
The classic bully, Coach Red checked all the boxes and even though the one-on-one scenes with Bobby Boucher were short, his shadow loomed large throughout the movie. 

4. Peter Gallagher as Chuck Cedar in Mr. Deeds
Only Peter Gallagher could give Chuck Cedar the distinguished, sleazy swagger that made him so memorable. His on-screen verbal sparring with Sandler’s Longfellow Deeds gives him an edge while giving us the laughs. 

Props has to be given to Erick Avari’s Cecil Anderson, who was Cedar’s toady. 

3. Matthew Glave as Glenn Guglia in The Wedding Singer
You know, you should write a song about this. You could call it “I got punched in the nose for sticking my face in other people’s business”. -Glenn Guglia

Don’t let Glenn Guglia’s style fool you. The guy was a real jerk. Playing the “cheating asshoe boyfriend who makes you wonder what the girl ever saw in him in the first place”, Guglia’s comeuppance was more than welcome thanks to Glave’s radical portrayal.  

2. Bradley Whitford as Eric Gordon in Billy Madison
Another character looking to take over the company, Eric Gordon came close but thanks to an aversion to business ethics and Steve Buscemi’s Danny McGrath, the good guys won in the end. 

1. Christopher McDonald as Shooter McGavin in Happy Gilmore
Who else could be numero uno than Shooter? Brought to life by Christopher McDonald, Shooter is not only Sandler’s greatest big screen nemesis, I put him up there with all the other bad guys that have come our way. He had the talent but his arrogance was his downfall. He might not have won the tournament but he will always wear the gold coat of villainy.