Happy Gilmore and Billy Madison. Since then, the company has produced over 50 films, mostly comedy live-action projects. However, Happy Madison Productions has also released two animated movies, and they couldn't be more different.

As of the writing of this article, Happy Madison Productions officially has two films in the works — Happy Gilmore 2 (a Happy Gilmore sequel featuring the returns of Sandler, Julie Bowen, and Christopher McDonald, per Netflix by Tudum) and Kinda Pregnant (a comedy starring Amy Schumer, Jillian Bell, Will Forte, and Damon Wayans Jr.).

Out of Happy Madison Productions' 50-plus movies, some of its most notable stories include Mr. Deeds, Anger Management, 50 First Dates, Click, Grown-Ups, Murder Mystery, and more. Basically, the company's standout films are also Sandler's best movies. Unfortunately, not all of them could be box office successes or receive positive reviews from critics and audiences alike. One of the Happy Madison Productions films that performed terribly in both regards was an animated flick that seemingly scared the company from making another of its kind for over 20 years.

Eight Crazy Nights Was A Box Office Dud In 2002

The Adult-Animated Hanukkah Film Was Also A Failure Among Critics

Happy Madison Productions and Adam Sandler made their first animated movie in 2002, and it was an epic failure. Eight Crazy Nights stars Sandler as Davey Stone, a Jewish man (and a curmudgeon) who gets into trouble with the law during the holidays in his small hometown. To avoid prison time, Davey agrees to do community service for Whitey Duvall, an older man who volunteers as a referee for the town's youth basketball league and has a ion for the holidays. Throughout Eight Crazy Nights, Whitey works hard to change Davey's perspective on his town, Hanukkah, and life in general.

Eight Crazy Nights' reception was a surprise to many, though. It came towards the end of Sandler's most prolific period as a filmmaker, as the 90s were full of hits for the actor.

Unfortunately, Eight Crazy Nights only grossed $23.8 million at the box office against a budget of $34 million, and critics gave it poor reviews. On Sandler's infamous holiday bomb has a Tomatometer score of 13 percent. Meanwhile, its Audience Score is 50 percent.

Many criticized the film's humor, unlikable protagonist, story, and more, resulting in one of the worst-received movies of Sandler's career. Eight Crazy Nights' reception was a surprise to many, though. It came towards the end of Sandler's most prolific period as a filmmaker, as the 90s were full of hits for the actor. So, Sandler's movie bombing was certainly a shock, and it made Happy Madison Productions hesitant to release another animated project for over 20 years.

It Took Over Twenty Years For Happy Madison To Produce Another Animated Film

Netflix Released Leo In 2023

Finally, 21 years after the release of Eight Crazy Nights, Happy Madison Productions developed another animated movie. Leo, a Netflix musical comedy, premiered in 2023, and it certainly redeemed the production company concerning its ability to make quality (and well-received) animated projects. Sandler's hit Netflix movie earned an 84 percent Tomatometer score on Rotten Tomatoes. Audiences also evidently loved Leo, as the film's Audience Score sits at an impressive 90 percent.

Leo is quite the comeback for Happy Madison Productions after Eight Crazy Nights (although it took over two decades). It certainly helps that the two movies couldn't be more different. Whereas Eight Crazy Nights is geared toward adults and has a cynical tone, Leo is suitable for kids and adults and is heartwarming. The films' animation styles also differ. Eight Crazy Nights uses 2D animation, while Leo features CGI animation, making the latter movie much more visually appealing. Ultimately, Sandler's animated Netflix comedy was so successful that it's getting a sequel, which is quite telling when comparing it to Eight Crazy Nights' reception.

Adam Sandler Was No Stranger To Animation

Sandler Has Starred In Other Animated Projects Outside Happy Madison

Even though it took 21 years for Happy Madison Productions to release its second animated movie, it didn't take that long for Adam Sandler to return to the medium. Ten years after Eight Crazy Nights​​​​​​​ bombed, Sandler voiced the lead character in Sony's Hotel Transylvania. He reprised the role in its two sequels —​​​​​​​ Hotel Transylvania 2 and Hotel Transylvania 3: Summer Vacation —​​​​​​​ with each installment in Sandler's Hotel Transylvania franchise performing better than the last at the box office.

So, Sandler has starred in five animated movies in his career. While his first one, Eight Crazy Nights, performed the worst, the actor's latest animated project, Leo, was one of his most well-received films. Perhaps Leo's success will persuade Adam Sandler and Happy Madison Productions to continue releasing animated movies.

Sources: Netflix by Tudum, Rotten Tomatoes