Top 100 Movies Of The 1990’s: #99 The Wedding Singer

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99. The Wedding Singer (1998)

Box Office: $80.2 million

Oscar Nominations: None

Oscar Wins: None

Stream For Free: HBO Max

Movierankings.net: 82/100

There is nothing subtle about Adam Sandler or his movies. Even his greatest movie, Uncut Gems, is an unrelenting panic attack disguised as a film. The lone exception to this rule is Punch Drunk Love which is a movie that seems to exist in the quiet moments. I like that movie less than most people and to me, Sandler never seems to fit in quite right there.

The Adam Sandler I know and love is perhaps best used in The Wedding Singer. This isn’t his funniest movie and it also won’t be the last time one of his movies makes it on this list. But this is the most charming Sandler has ever been and it’s the first time where you can see he does have some real acting talent when he wants to use it.

But as I said earlier, there is nothing subtle about Sandler’s performance in The Wedding Singer or the movie as a whole. Every shoe-horned 80’s reference, the wild costume design and the way the camera will linger and almost pause on each joke; this movie makes no secret about what they are trying to do here. And I think that’s perfectly fine. It’s a movie that wears its heart on its sleeve and there’s something refreshing about a movie that is more concerned with being honest than clever.

The greatest thing this movie has going for it is the chemistry between Sandler (as Robbie Hart) and Drew Barrymore (as Julia Sullivan). When you are watching this, it feels like Barrymore’s natural ease on camera rubs off on Sandler and he’s able to relax.

This is the rare comedy that has a great 3rd act. Usually, comedies fall apart at the end because the plot needs to take over and the jokes are set aside. But this script by Tim Herlihy takes the tired rom-com storyline but adds in funny characters like Billy Idol. Mix that with the audience caring so much about Robbie and Julia by that point, it makes for one of the most satisfying endings you’ll see in any comedy.

Despite the abundance of charm, this isn’t a perfect movie. Some of the jokes don’t land and the mocking of George (Alexis Arquette) seems unnecessarily cruel in 2022. The movie itself seems to feel that same way as you barely see George in the second half of the movie and instead wisely focuses on making an asshole like Glen Gulia (Matthew Glave) the butt of the joke. Having said that, I’m not sure litigating movies that are 25 years old from the sensitivities of 2022 is a very fair practice. Doing a countdown like this, I’m sure these types of instances will continue to come up and I’ll talk about them but there should be some understanding here. We should learn from the shitty parts of the past but that doesn’t mean we can’t enjoy or appreciate the good elements. 

Although it was never #1 at the box office in any of the weekends it was released in theaters, The Wedding Singer was a very successful movie. It has the misfortune of coming out in the middle of Titanic’s 15 week in a row stretch where it was #1 each weekend at the beginning of 1998. The Wedding Singer did finish #2 in three straight weekends and made more money than Happy Gilmore and Billy Madison combined. This really was the movie that launched Sandler into becoming a movie star. His next two movies (The Waterboy and Big Daddy) each would double what The Wedding Singer made. Having Drew Barrymore as the other romantic lead legitimized Sandler to a whole new audience for him.

I should probably mention the director Frank Coraci. He also directed The Waterboy (which also came out in 1998) and I like this a lot better. He’s not particularly skilled but does a nice job getting out of the way of Sandler and Barrymore and letting the strength of the movie shine uninterrupted. He would later go on to direct the box office bomb Around The World In 80 Days but after that, his next five movies starred Sandler and/or Kevin James. After the 80 Days disaster, he seems to know what his limitations are and because of that, he’s directed movies with domestic box office grosses of $80 million dollars four different times. That’s as many as Martin Scorsese.

This is not Sandler’s funniest movie of the decade and as I said earlier, it’s also not his best. But it does have the characters I care about the most and a natural chemistry between the leads that rival any movie. The great Roger Ebert really missed the mark (as he would on a lot of comedies after 1990 despite being the best critic I’ve ever read) and gave this movie one star when it came out and I think that’s really unfair. Critics loved using Adam Sandler as a punching bag for years but they missed out on one of the funniest guys of his generation and in this case, one of the most charming movies of the decade.