2000s Comedy Movies With Chris Rock, the Wayans Brothers and Bernie Mac’s Best Roles

The 2000s don’t feel like they were that long ago; however, so much has changed since then. Technology and the entertainment industry are among the most rapidly changing sectors, with new content coming out across dozens of streaming services on a daily basis. There are now more films and TV shows to watch than ever before, but with all the other changes taking place around us we’ve also seen shifts in our culture that have left audiences nostalgic for the carefree humor found in 2000s comedy movies.

Nowadays, creatives are much more sensitive to how other might negatively respond to their work, leaving many to tiptoe around the risk of being canceled by skirting controversial topics altogether. To be fair, some of the films made in the first decade of the millennium are hard to watch back because of their total lack of boundaries, but there are a good number which have aged well and continue to put a smile on our faces, such as the titles on our list below.

12. Black Dynamite (2009)

IMDb: 7.4/10

Rotten Tomatoes: 85%

Michael Jai White, Byron Minns and Tommy Davidson star in 2009’s Black Dynamite, an action comedy about a kung fu fighter who becomes so enraged by the death of his brother and poisoning of his neighborhood that he heads to the White House. The Scott Sanders-directed project takes place when Richard Nixon was president (early 70s), and it’s also been presented in the form of an adult animation series on the Cartoon Network.

11. Juno (2007)

IMDb: 7.4/10

Rotten Tomatoes: 88%

The next time you’re scrolling through Hulu in need of a laugh, check out Michael Cera and Elliot Page (formerly Ellen) in Juno. The trans actor played a pregnant teenager in the 2007 movie, who selects a failed rockstar (Jason Bateman) and his wife (Jennifer Garner) to adopt her unborn child. Michael Cera, Rainn Wilson, Allison Janner and Valerie Tian also appear.

10. Scary Movie (2000)

IMDb: 6.3/10

Rotten Tomatoes: 43%

The Wayans brothers’ most talked about movie is definitely White Chicks, but we can’t forget what they brought to the table in 2000’s Scary Movie. The star-studded cast cleverly parodies many of the biggest moments in pop culture at the time, including Scream, The Matrix, I Know What You Did Last Summer, The Sixth Sense and more. There have been several other films released in the franchise since, with the fifth arriving in 2013.

9. Little Miss Sunshine (2006)

IMDb: 7.8/10

Rotten Tomatoes: 91%

Just like the title implies, Little Miss Sunshine is sure to bring some much-needed brightness into your life. Valerie Faris and Jonathan Dayton teamed up to direct the 2006 flick, which follows a young Abigail Breslin in the role of Olive Hoover. She doesn’t look like your average beauty queen, but Olive has dreams of winning the Little Miss Sunshine Contest in California, and her eccentric family goes above and beyond to put their differences aside and get her there on time.

8. Shrek (2001)

IMDb: 7.9/10

Rotten Tomatoes: 90%

Several 2000s comedy movies of the animated variety are worth revisiting, such as Shrek and its sequel. Beloved actor Eddie Murphy voices Donkey throughout the adventurous film franchise and Michael Myers’ iconic Scottish accent is just a small part of what makes everyone’s favorite ogre so funny. At this time, Shrek is available for streaming with a Peacock subscription.

7. The Longest Yard (2005)

IMDb: 6.4/10

Rotten Tomatoes: 62%

We would be remiss not to include any of Chris Rock and Adam Sandlers many movies on our list, such as The Longest Yard. The 2005 sports comedy sees Sandler as a former pro-footballer turned criminal whose stint behind bars helps him to revamp his athletic career as he preps his fellow inmates to face off against the guards on the field. Rock plays the prison’s Caretaker, R&B star Nelly appears as Megget and Terry Crews is Cheeseburger Eddy.

6. Forgetting Sarah Marshall (2008)

IMDb: 7.1/10

Rotten Tomatoes: 76%

Adulthood is a non-stop rollercoaster of emotions, and arguably one of the lowest lows on that ride comes from experiencing the pain of a breakup. When you’ve had enough of sobbing over your own loss, sometimes the best thing you can do is find humor in another’s pain and the ultimate movie for that is Forgetting Sarah Marshall. Jason Segel plays a struggling musician Peter, whose TV star girlfriend (Kristen Bell) suddenly dumps him. When he decides to go to Hawaii to heal from the pain, fate puts Sarah and her new man (Russell Brand) at the same hotel, making for one memorable vacation.

5. Madea’s Family Reunion (2006)

IMDb: 5.3/10

Rotten Tomatoes: 93%

It’s hard to look away anytime Tyler Perry channels his feminine alter ego on the big screen, but Madea’s Family Reunion will always be a classic. In 2006, the infamous matriarch was hoping to have her relatives gather together, though the relationship troubles of her nieces are raising some issues. Elsewhere, Madea is now the guardian of a rebellious teen named Nikki (played by Keke Palmer) who only adds more turmoil to the mix.

4. Bruce Almighty (2003)

IMDb: 6.8/10

Rotten Tomatoes: 57%

Another 2000s comedy movie that Peacock users can readily stream is 2003’s Bruce Almighty, in which the legend himself, Morgan Freeman, plays God. Other industry icons who star in the film are Jim Carrey and Steve Carrell, the latter of whom appears in the 2007 spin-off, Evan Almighty which is equally as funny and also features Wanda Sykes.

3. Pootie Tang (2001)

IMDb: 5.3/10

Rotten Tomatoes: 63%

In the early 2000s, Chris Rock and Wanda Sykes put their musical chops to the test in Pootie Tang, a film adapted from a comedy sketch on the former’s HBO series. Pootie (Lance Crouther) is a cool-walking, smooth-talking lady’s man who inspires many others in his neighborhood. Our star’s only enemy is Robert Vaughn (Dick Lecter), who owns a company that makes everything from cigarettes to fast food, though he proves to be no match for Pootie’s confidence.

2. Mean Girls (2004)

IMDb: 7.1/10

Rotten Tomatoes: 66%

There’s been a Mean Girls resurgance in recent months thanks to the 2024 musical version of the film. No matter how much Reneé Rapp and Avantika Vandanapu impressed us with their performance in that, they’ll never be able to out-do what was done by Lindsay Lohan and Rachel McAdams in the original 2004 effort. The high school dramedy that psychoanalyzes clique culture is currently streaming on Apple TV+, Paramount+ and Showtime.

1. Bad Santa (2003)

IMDb: 7.1/10

Rotten Tomatoes: 75%

If you’re missing the comedy stylings of the late Bernie Mac, you can always revisit his work alongside Billy Bob Thornton in Bad Santa. Terry Zwigoff directed the raunchy 2003 movie, which comes from the minds of Ethan and Joel Coen. Marcus Skidmore and Thornton play conmen who reunite once a year during the holidays to rip off shopping malls on Christmas Eve. Unfortunately for them, the latter is off his game and his drunken behavior catches the attention of a mall security guard (Mac), causing him to question everything.