The 10 Best Dave Chappelle Movies You Must Watch

Now that you have seen his stand-up comics, it’s time to watch his hilarious films too

If you are on “Saturday Night Live”, then you must know who Dave Chappelle is. 

Even if you didn’t watch a single episode, you must have come across his comic gigs online. 

Whatever mood you are in, a few minutes of Dave’s words will surely make your day. You just can’t continue being grumpy. 

In fact, his Emmy nominated Netflix show “Chappelle’s Show” has become a household name now. So, it’s impossible to not know Dave Chappelle in some way or other. 

Now, let’s break away from the image of a stand-up comedian and enter the world of him being a Hollywood actor

Well, well, well, what can I say, he never fails to charm us. 

Now enough talking. I know you are already with your watchlist and furiously add them all. So, without further ado, let’s get started. 

Below I have listed the 10 best Dave Chappelle movies you must watch this weekend. They are not only hilarious but will definitely add some value to your life

1. A Star is Born (2018)

Okay, let’s start with the best. In simple words, Dave Chappelle is being Dave Chappelle in this movie. We can see his originality throughout. Such effortless acting. And how can anyone forget his monologue? 

Skilled musician Jackson Maine meets – and loves – struggling artist Ally. She had almost abandoned her goal as a singer until Jackson put her in the limelight. But even as Ally’s career begins, her relationship side breaks down, while Jackson battles a continuous struggle with his own inner devils.

Where can you watch: Amazon Prime Video, HBO Max, and Apple TV.

Related: Dave Chappelle Net Worth

2. You’ve Got Mail (1998)

A hard-working boutique bookseller, Kathleen Kelly (Meg Ryan) hates the proprietor of a company Foxbooks shop, Joe Fox (Tom Hanks). 

However, when they interact online, they start a passionate and secret Internet relationship, which overlooks the actual identity of one other.

 Finally, Joe finds out that his company competitor is really his charming lady with whom he is connected. He now must fight to reconcile the online love he has had for his actual hate.

Where can you watch: Amazon Prime Video, HBO Max, Apple TV

3. The Nutty Professor (1996)

Sherman Klump (Eddie Murphy), the bright and chubby scientist, discovers a miraculous method for weight loss. 

When Carla Purty (Jada Pinkett) goes wrong with the date with a chemistry student, sad Klump attempts the remedy alone. 

While he loses 250 pounds immediately, there is a second personality: a braggart who names himself Buddy love. Buddy is more renowned than Sherman but he rapidly loses control of his attitude and nasty behavior.

Where can you watch: Amazon Prime Video, Apple TV

4. Robin Hood: Men in Tights (1993)

Campaigning Lord Robin of Loxley (Cary Elwes) escaped Jerusalem and came home to discover that the wicked Prince John (Richard Lewis) took the estate of his family and abused citizens.

 In order to guide Robin to return home, he enlists Blinkin (Mark Blankfield), Will Scarlett O’Hara (Matthew Porretta), and Little John (Eric Allan Kramer). 

Robin is also hoping to court this lovely maid (Amy Yasbeck), but the difficulty is her chastity belt.

Where can you watch: Amazon Prime Video, Apple TV

5. Dave Chappelle’s Block Party (2005)

Now let’s move a bit from the fictional world and dive into documentaries. 

Dave Chappelle’s Block Party” is a documentary written and hosted by the comedian himself. 

The film revolves around a block party in the summer of 2004 organized by Dave in Brooklyn. The doc features some of the most famous buildings, like the Broken Angels House. 

In fact, the music used in the documentary is dedicated to music producer J Dilla, who succumbed to lupus before the release. 

Where can you watch it: Amazon Prime Video, Apple TV 

6. Undercover Brother (2002)

Undercover Brother” is hired to enter a dangerous subterranean organization lead by The Man, which has been bursting down and is poised to take over the firm. 

Our hero must first be able to endure the utmost adaptation and trade his tennis sweatshirts and penny loafers in partnership with the astonishing Sistah Girl (Aunjanue Ellis). 

When the transition has ended he will take on Operation Whitewash’s wicked culprits.

Where can you watch: Amazon Prime Video, Peacock, Apple TV.

7. Blue Streak (1999)

When a robbery went wrong, Miles (Martin Lawrence), before being caught, conceals a diamond on a building site.  Miles returned to the site of his gem after having to serve two years and found that it is now a police station. 

Camouflaging himself to penetrate the building as a freshly appointed cop and seeking to find the gem, Miles stops a fleeing thief. 

 Superior Rizzo (Graham Beckel) is amazed by his fast action and team with the clumsy Casey investigator (Luke Wilson).

Where can you watch it: Peacock, Hulu, Amazon Prime Video, Apple TV

8. Joe’s Apartment (1996)

This comedy, which draws its inspiration from a popular short film, centers on Joe, a young man who relocated to New York City, from Iowa.

Joe discovered after establishing in his dreadful flat that there is an army of cockroaches chatting and singing. 

Even though he has numerous bugs for his housemates, Joe finds them pleasant and kind. They help him to court the pretty Lily (Megan Ward) and battle with his middle owner (Don Ho).

Here, Dave does the voice-over of one of the cockroaches. 

Where can you watch: Amazon Prime Video, Apple Tv

9. Con Air (1997)

The righteous military ranger Cameron Poe (Nicolas Cage) goes back to his wife (Monica Potter) but has to travel home on an aircraft known as “Jailbird” on transit to jail with some of the worst offenders. 

 In addition to the Diamond Dog (Ving Rhames) and Baby-O (Mykelti Williamson), Cyrus Grissom (John Malkovich) is an excellent serial murderer and is unleashing a violent mid-flight escape scheme.

Poe tries to disrupt his scheme in his secret collaboration with the U.S. Marshall Vince Larkin (John Cusack).

Where to watch: Amazon Prime Video, Apple TV

10. Half Baked (1998)

When a crew member is jailed for murdering a police horse in New York City by giving junk food, 3 slacking stoners are compelled to get off their feet and fund the bail by selling marijuana stolen from a drug laboratory.

This is a hazardous project, but, hey, they are all stand-up people who would do whatever they could to aid a needy buddy.

Where can you watch: Peacock, Amazon Prime Video, Apple TV


Did you make your watchlist? Surely you did. Now all you need to do is grab your snacks and slide under the blanket. 

Dave Chappelle never failed to make me laugh. And I am sure you will feel the same. 

If you are an “old movies” lover, then the above list is specially made for you. 


P.S: I researched and wrote this article to add some laughter and value in your life. I hope you grab some lessons and execute them into your life.

"As an Amazon Associate I earn from qualifying purchases"