The Five Best Dave Chappelle Movies of His Career

Half Baked

It’s kind of hard to imagine that Dave Chappelle was ever booed off stage isn’t it? But it did happen way back in the day when he was first getting his start and trying to become someone big. Back then however it seems as though he hadn’t really come up with his off the wall personality that has afforded him so much notoriety throughout the years and likely hadn’t quite gained the courage to keep pushing forward. Obviously that moment when he was booed so badly that he had to leave the stage for a moment did something though as he’s been prominent in movies and TV for quite some time now. He’s been seen as a controversial character for his humor now and again but thankfully this hasn’t really seemed to detract from his performances or sent him into seclusion as one might have believed it could.

Here are his five best movies.

5. A Star is Born

Colin McCormick of ScreenRant has pointed out that there’s a lot about this movie that more than a few people missed, but in truth if you got the gist of it, that sometimes the hurt a person feels and the demons they deal with are a little too strong, then you got enough of it. Dave plays the friend of the male lead, a comforting and solid presence in a life that is otherwise spinning slowly out of control and has only a few grounding points. Obviously that’s not enough as Jack finds later in the movie that his inner demons are just too much to deal with and hangs himself.  This movie was one of the favorites of 2018 and it’s not too hard to see why.

4. You’ve Got Mail

So here’s a tip, if you want to nitpick everything about this movie and agree that it’s deeply flawed then reading up on Megan Garber’s article in The Atlantic is definitely up your alley since, let’s face it, tearing into movies is a favored pastime of some folks. But if you really want to enjoy a movie that’s about two people who are at odds with one another because one of them belongs to a family that owns a major chain of bookstores and the other is a woman that owns a quiet little bookstore loved by the community, then it’s probably best to watch the movie and disregard a lot of the critics that would claim otherwise.

3. Robin Hood: Men In Tights

Mark Mancini of Mental Floss came up with a pretty interesting list of facts about this movie that are worth looking at since in retrospect Mel Brooks is really one of the only guys in the world that can get away with a movie like this and not be so highly criticized for it. If anyone remembers Blazing Saddles, and plenty of us do, his use of so many different elements that are seen as trigger warnings these days was rampant within just about every other scene. But in this movie he does tone it down a bit even if some of the stuff you see might still be deemed a trigger warning. You know, like straight couples and the token black guy that happens to be awesome in his role.

2. Con Air

It’s kind of hard to admit it but Dave has been a prop in a couple of movies since he’s just there to take up space when in truth just about anyone could have been cast into his part. But the great thing about casting him is that he does lend a good amount of talent to just about any role and makes it a little easier to believe. As an inmate in this movie though he almost doesn’t seem to fit in until one realizes that he’s the kind of guy that serves as the yes-man for the truly psychotic and dangerous criminals and isn’t all that dangerous himself. In reality this is the guy that just goes along with the crowd.

1. Half Baked

If you expected any other movie to be at the top of this list then you haven’t been paying attention to Chappelle for a long, long time. Half Baked was without any doubt at all his absolute best movie since it not only gave him the freedom to just go wild, but it was actually one of the more socially acceptable movies around when it came to drug use no matter what people might say. It was funny, it was crazy, and it was the kind of movie you didn’t even bother to take seriously since the movie wasn’t designed to take itself seriously. The story of three potheads that have to raise the money to get their friend out of jail is about as simple as it gets, but it’s also beyond hilarious thanks to some of the gags they pull throughout the movie.

Dave Chappelle has calmed down a bit throughout the years, but he’s still hilarious.


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