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Teashade Reviews Vol. 1 ~ Chappelle's Show (Season 1)

Updated on May 27, 2017
Chappelle's Show opening logo. Image copyright of Comedy Partners.
Chappelle's Show opening logo. Image copyright of Comedy Partners.


2003 saw the launch of one of television's most successful sketch shows - Chappelle's Show, hosted by none other than stand-up legend Dave Chappelle. Having been involved in the comedy scene since the late 80's, Chappelle managed to work his way up through the stand-up arena, cementing his position as one of the top-tier comedians through the 90's and early 2000's.

Despite his personal frustrations at trying to produce his own television shows and films (culminating in his disappointment at the botched film Half-Baked he co-wrote with fellow stand-up comedian Neal Brennan), Chappelle persevered and finally managed to secure his own television show on Comedy Central.

Chappelle's Show has gone on to become one of the most popular comedy shows in modern history - but how does its first season stack up? Today, we'll be reviewing the entire first season - comparing sketches and structure from a critical viewpoint and figuring out what works and what doesn't.

Whilst not as intrinsically complicated as lengthier feature shows, Chappelle's Show does provide a diverse range of content to break down and analyse. So, without further ado, let's dive in and give it an ol' fashioned Teashade look!

Ambitious Introduction

The first season of Chappelle's Show doesn't hold back - right from the get-go we're introduced to several sketch characters that push the limit of comedy. In the very first episode, Chappelle introduces the first of many Frontline parody sketches - with show host Kent Wallace (played by William Bogert) meeting with a black white supremacist named Clayton Bigsby (played by Dave Chappelle). The white supremacist sketch was quite controversial - but it worked in drumming up the show's notoriety and drew in a larger subsequent following in future episodes.

The infamous black white supremacist Clayton Bigsby, played by Dave Chappelle. Image copyright of Comedy Partners.
The infamous black white supremacist Clayton Bigsby, played by Dave Chappelle. Image copyright of Comedy Partners.

Episode two saw the introduction of yet another controversial character - the first of several recurring characters that Chappelle would use over the course of the series. Known as Tyrone, this parody of a drug addict left a lot of people feeling a tad uncomfortable - especially as the first segment this character was introduced in was for a Drug Awareness speech at a (fictional) primary school. Dave Chappelle would revisit this character twice more during the first season - but thankfully, in a more disciplined and approachable way than his first outing.

The drug addict known as Tyrone, played by Dave Chappelle. Image copyright of Comedy Partners.
The drug addict known as Tyrone, played by Dave Chappelle. Image copyright of Comedy Partners.

Episode three continued the onslaught of ambitious and controversial sketches with a Zapped skit - a parody of MTV show, Pranked. The sketch, whilst funny at times, also served as a reminder of the extremities of what people are willing to do for attention - and is oddly reminiscent of today's modern prank culture on social media, some fourteen years later.

Episode four saw the gradual winding down of Chappelle's callousness - with the Reparations sketch. This sketch in particular saw the successful transition of Chappelle's comedy from outright controversial to outrageously funny, sprinkled with grains of truth. The fourth episode was the beginning of the first season's settle into form - as it would only continue to grow and refine its art from its first month on the air.

Refined Form

With Chappelle's Show now entering its second month of syndication, the show introduces several new sketch styles and also instigates a trend of revisiting some of these sketch styles over subsequent episodes. Some sketches - such as the Entrepreneurial Product & Services skits, Great Moments in Hook-Up History skits and Paul Mooney's Ask A Black Dude skits are all revisited several times over the course of episodes five, seven, eight and ten.

Chappelle also introduces a sketch series known as Real Movies - interpreting what would really happen in some of Hollywood's famous films in the real world. This particular segment is introduced in episode seven with a parody of The Matrix and is revisited again in episodes eight and ten with parodies of Ghost, Half Baked and Deep Impact.

Members of popular group Wu-Tang Clan, advertising their fictional Wu-Tang Financial business in the Entrepreneurial Products & Services sketch. Image copyright of Comedy Partners.
Members of popular group Wu-Tang Clan, advertising their fictional Wu-Tang Financial business in the Entrepreneurial Products & Services sketch. Image copyright of Comedy Partners.

Whilst Chappelle sprinkles some independent one-off sketches into the episodes, a majority of his sketches involve recurring stories or perpetuate a certain theme or issue prevalent in modern culture. Issues such as race, gang culture, the entertainment industry and pop culture are frequently addressed and parodied in some form. These are most prevalent in the Mad Real World and Trading Spouses parody sketches, subsequent Frontline segments and the Turn Up My Headphones mix-tape performance.

Chappelle's Show further refines its form by implementing occasional guest segments - most commonly in the form of artists performing a song or rap either live or in a pre-filmed segment. This special segment gives artists a chance to exhibit their talents to a mainstream audience and help gain popularity - a segment that is commonly seen on late night shows.

Bowing Grace

The third and final month of Chappelle's Show's syndication saw Chappelle further refine his art into a perfect balance of ambition and refinement. Revisiting earlier sketch segments such as Paul Mooney's Ask a Black Dude, Chappelle also brought in a slew of fresh content for his fans - in some of his best performances yet.

There were a few one-off skits, such as the Vice City and Blackzilla sketches, that managed to greatly entertain gaming and cinema buffs. The character of Tyrone was revisited once again in cameo appearances in two other sketches - namely the History of Gang War sketch and Magic Camera skit. Artists such as De La Soul and Blackstar performed in pre-recorded segments in an episode each.

The true highlight of the third month, however, were two specific sketches - the Player Haters Ball skit and the R Kelly music video parodies. Both of these skits proved to be a hilarious and satirical look at comedy culture and the entertainment industry - resonating in popular acclaim.

There were, however, a few skits that weren't as well-received as others. Some sketches, such as the Make-a-Wish and Sports Trolling segments, fell a bit flat. Others, such as the 2-minute Comedy Special and Diarrhea Choir segments bordered on the line between flat and childish.

Chuck Taylor of News 3, a recurring news reporter throughout Season 1 played by Dave Chappelle. Image copyright of Comedy Partners.
Chuck Taylor of News 3, a recurring news reporter throughout Season 1 played by Dave Chappelle. Image copyright of Comedy Partners.


Overall, Chappelle's Show manages to introduce its audience to a fresh take on comedy sketches - refining traditional styles with masterful flair whilst also implementing a few fresh new skits to declare its independence from mainstream comedy. As a whole, the season is solid, providing quality entertainment to fans of sketch comedy and critics alike. Chappelle's Show would go on for an additional two seasons - with the first laying the groundwork for what would become Dave Chappelle's trademark style of comedy.

Ultimately, I've awarded Chappelle's Show Season 1 an 8 out of 10 for its final mark. Whilst the show pushed the benchmark of quality entertainment, it wasn't without its faults. Some of the humour fell flat or was outright immature, which was a thorn in an otherwise smooth voyage of a maiden season.

4 stars for Chappelle's Show ~ Season 1

© 2017 Teashade Benu


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    • Teashade Benu profile imageAUTHOR

      Teashade Benu 

      19 months ago from Australia

      There certainly were a myriad of great sketches on the show wasn't there? It's been nice revisiting the series after so many years.

      Thank you for your comment!

    • Angel Guzman profile image

      Angel Guzman 

      19 months ago from Joliet, Illinois

      I remember looking forward to each episode. Clayton Bigsby, the Mad Real World, When Keeping it Real Goes Wrong, True Hollywood Stories were my favorite sketches. The wrap it up box too, lol.


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