30 Years Ago Today: Adam Sandler Made One Of The Worst Buddy Cop Movies Ever Made

Adam Sandler's best movies are some of the most beloved comedies of the last few decades. His bad movies? They're some of the worst comedies ever made, and I think it's fair to say even the man himself knows that. For every "Punch-Drunk Love" and "Hustle," there's a "Ridiculous 6" or "Pixels." Sandler is also responsible for one of the worst movies ever made, having produced the lousy Dana Carvey vehicle "The Master of Disguise," which to this day maintains a 1% critic score on Rotten Tomatoes (turns out one critic at Long Island Press liked it). At least Sandler can claim that his 1996 buddy cop effort "Bulletproof" beat "The Master of Disguise" by a whole seven percentage points.

Three decades ago on this date, the former "Saturday Night Live" star teamed up with Damon Wayans (who also had a brief stint on that same show) to deliver an abject buddy comedy. Seriously, Clint Eastwood was once paired with a trained orangutan for an entire film and got better results. "Bulletproof" saw Wayans play an undercover cop who has to haul his former friend, Sandler, across the country to testify against his boss. Hilarity was supposed to ensue, but instead we got some of the most fascinatingly awkward attempts at comedy yet put to film.

Many of Sandler's worst movies came as a result of his Netflix deal, which was finalized in 2014 and has thus far yielded such dross as the aforementioned "The Ridiculous 6" and something called "The Do-Over," which only managed to notch one more percentage point on the Tomatometer than "Bulletproof." But even with these modern missteps in mind, his 1996 buddy comedy with Wayans remains one of his most egregious films.

Aside from the great buddy comedies we all know and love, there are plenty of underrated buddy comedies just waiting to be discovered. "Bulletproof" belongs to neither category. The film sees Adam Sandler play Archie Moses, a car thief who has a side gig working for drug kingpin Frank Colton (James Caan). During a drug deal gone awry, Moses learns that his best friend Rock Keats (Damon Wayans) is actually Detective Jack Carter, who's been working undercover.

Moses accidentally shoots Carter during the resulting confrontation, but he somehow survives, after which he's tasked with transporting a recently arrested Moses across the country so he can testify against Colton. Needless to say, the two aren't on good terms. Thus, we have the basis for what should have been a decent buddy comedy. For whatever reason, however, Wayans and Sandler just never seemed to click.

Perhaps part of the problem was director Ernest R. Dickerson, who had previously overseen the 1992 crime thriller "Juice," the 1994 actioner "Surviving the Game," and the 1995 horror comedy "Tales from the Crypt Presents: Demon Knight." While "Juice" earned positive reviews and remains a cult classic, and many horror fans still praise "Demon Knight" despite its negative critical reviews, "Surviving the Game" was a massive bomb. What's more, Dickerson didn't necessarily seem like the right fit for an Adam Sandler/Damon Wayans buddy comedy. It's not surprising the director later told DVDTalk that he'd "like to just erase that whole experience." He wasn't the only one.

Ernest R. Dickerson wasn't solely to blame for "Bulletproof" flopping. Joe Gayton and Lewis Colick's script certainly didn't help. The main joke in one scene is that Adam Sandler needs the bathroom while he's chained to Damon Wayans. When he's finally allowed to relieve himself, Wayans yanks the chain mid-stream and the scene ends with Sandler yelling "I got piss on me!" It's basic stuff.

But the most surprising aspect of the movie is the lack of any comedic spark between its two leads. Anyone who grew up on "In Living Color" will know Wayans' comedic chops have never been in question. Similarly, younger millennials who spent afternoons after school watching "My Wife and Kids" will recall how Wayans' heartfelt authenticity offset his wry sense of humor. For some reason, however, he's awful in "Bulletproof." He seems genuinely uncomfortable in many of his scenes with Sandler, and the lack of chemistry between the pair is startling. The whole thing just feels very awkward.

Unsurprisingly, "Bulletproof" did not fare well critically or commercially. Sandler's biggest box office bomb ever remains "Little Nicky," which only made $58.3 million on an $85 million budget. "Bulletproof" isn't far off, though. The film made just $21.6 million on an estimated budget of $25 million. Meanwhile, critics accused it of being "preposterous," "unfunny," and even in the case of Film.com's Keith Simanton (via Rotten Tomatoes), "homophobic." No wonder Wayans' movie career flamed out following the film's release. Otherwise, Sandler and Netflix are doing their best to convince us the actor's best days are behind him, and they could have pulled it off if "Bulletproof" didn't exist.