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Teashade Reviews Vol. 2 ~ Chappelle's Show (Season 2)

Updated on June 7, 2017
Dave Chappelle impersonating and promoting celebrity Samuel L. Jackson's beer. Image copyright of Comedy Partners.
Dave Chappelle impersonating and promoting celebrity Samuel L. Jackson's beer. Image copyright of Comedy Partners.


2004 saw the premiere of Chappelle's Show's second season. Riding the wave of the first season's commercial success, Dave Chappelle returns to host the show - armed with a variety of new and original sketches. The team from season one (including co-writer Neal Brennan and actors Charlie Murphy, Mos Def and Donnell Rawlings) return to build on the foundation the first season established. New sketches are performed whilst also referencing past events and cameos from popular skit characters from the previous season.

But, how does it compare to the first season? Does season two of Chappelle's Show continue the upward trend of success or does it fall flat?

A Warm Return

Right off the bat, Chappelle's Show digs into its sketch comedy - referencing last year's Entrepreneurial Products & Services skits in the form of Samuel L. Jackson Beer. The main difference this time around is that Dave Chappelle is impersonating a celebrity instead of the actual celebrity advertising their fictional product.

Celebrity impersonations was originally a mildly recurring theme in the last season - specifically with two R. Kelly skits and a few parodies of film characters. This season, however, Dave Chappelle ups the ante by adopting a more ambitious and aggressive approach towards Hollywood actors and artists. Dave impersonates famous celebrities such as R. Kelly, P. Diddy, Samuel L. Jackson, Lil' Jon, Rick James, Prince and a myriad of other lesser known celebrities who have been in the news or involved in some kind of controversy in recent times.

These sketches are peppered throughout the season, appearing in about half of season two's episodes - specifically episodes one, two, four, five, six, seven, ten and thirteen.

Not content with just impersonations, however, Dave also brings back some of his iconic characters from season one - namely Tyrone Biggums the addict, Chuck Taylor the news anchor, Leonard Washington the tough guy and Silky Johnson from the Playa Haters Ball. This season also sees the emergence of other prominent skit characters as well from Dave Chappelle's supporting cast - with the introduction of Donnell Rawling's 'Ashy Larry', Paul Mooney's 'Negrodamus' and Karl Lake's 'Robot Dancer'. The supporting cast from the Playa Haters Ball (played by Charlie Murphy, Donnell Rawlings and Yoshio Mita) also return in a new unfinished sketch known as the 'Time Haters'.

In a similar fashion to the first season, Chappelle's Show also introduces a couple of new sketches that recur over the course of the second season. The first example, 'When Keeping It Real Goes Too Far' tells of moments in which people escalate their current situation against their favour - in a kind of reverse take on season one's 'Great Moments in Hook-Up History' segments. Another example is Paul Mooney's 'Mooney on Movies' skit - in which he and two white ladies critique several films such as Gone with the Wind, Barber Shop and The Last Samurai. This sketch parodies Chappelle's own 'Real Movies' segments he performed in the previous season.

Some otherwise notable examples of great sketches during the second season include the 'Oprah' sketch and subsequent cameos - as Dave Chappelle 'leaves' his job to live with Oprah only to find out her newborn child isn't his. Another example is 'A Day in the Life of Lil Jon' - where Dave Chappelle adopts the role of artist Lil Jon and parodies him in real life scenarios with his trademark vocabulary of 'What', 'Yeah' and 'Okay'. Lastly, the 'World Series of Dice' sketch is a definite winner - as it not only introduces the recurring sketch character of Ashy Larry (played by Donnell Rawlings) but also cameos sketch character Leonard Washington (played by Dave Chappelle) and fellow comedian Eddie Griffin as dice player Grits 'n' Gravy.

The future seer known as Negrodamus, played by Paul Mooney. Image copyright of Comedy Partners.
The future seer known as Negrodamus, played by Paul Mooney. Image copyright of Comedy Partners.

Traditional Ambition

Season two of Chappelle's Show continues to build on the foundation of its predecessor - not just in its sketch comedy but also in the structure of its episodes. The first month of syndication follows the tradition of hitting hard and fast with ambitious sketches that are both funny and socially relevant.

This is most evident in episode one's 'Racial Draft' sketch - a skit in which Chuck Taylor (played by Dave Chappelle) co-hosts a racial draft in which each race selects a celebrity to join their community. Another example includes episode two's 'WacArnold's' sketch - in which Dave Chappelle plays a young working man who struggles to find happiness in his hometown despite having a job and earning an income. The skit itself is meant to parody fast food ads that depict working class people as happy in their advertisements but rings eerily true to the reality of the world.

Perhaps the most controversial example of Chappelle's ambition in season two comes from the 'Niggar Family' sketch - a skit set in an idyllic black-and-white world similar to the old American family advertising propaganda in the 50's. This sketch plays on the n-word with the controversial setting of it being the surname of a white family. The skit itself is designed to poke fun at racist culture whilst also reminding the audience that the n-word itself is just a word - it's only offensive if people allow it to be.

Despite the ambitious approach towards cultural issues, Chappelle's Show also has some more relaxed comedic moments as well. Episode two introduces the first of Paul Mooney's sketch characters in the form of Negrodamus - a parody of Nostradamus aimed at reading the future and predicting the outcomes of somewhat questionable future events such as the fate of Michael Jackson and other pop culture icons.

Dave Chappelle also parodies himself in a sketch in episode three - in a segment known as 'The Three Daves'. This sketch provides a humourous look at Chappelle's life at three different ages and providing several scenarios in which each type of Dave would react. The sketch itself proved to be funny - but more importantly, it shed light on addressing the ever-changing metamorphosis and mentality of people as they grow older.

Whilst Chappelle's Show's second season definitely continues to push the border of controversial comedy, it also manages to find a more nuanced and mature balance in the process. This trend continues on, for the most part, into the rest of the season.

Charlie Murphy recounting stories of his adventures with famous celebrities in Charlie Murphy's True Hollywood Stories. Image copyright of Comedy Partners.
Charlie Murphy recounting stories of his adventures with famous celebrities in Charlie Murphy's True Hollywood Stories. Image copyright of Comedy Partners.

Refined Transition

As Chappelle's Show entered its second and third months of syndication, it also transitioned into a more defined episodic structure - with some episodes containing a form of a 'self-contained' story. These contained episodes are most evident in episode eight's 'I Know Black People' quiz show sketch, episode eleven's 'Failed Sketches' series and episode twelve's 'Wayne Brady' episode - in which Wayne Brady himself takes over as host for a majority of the episode.

Whilst the contained episodes structure isn't new to television, it was somewhat interesting to see Chappelle's Show, a comedy show of all things, adopt such a style. It certainly wasn't a bad thing - it was a refreshing change of pace for the series and helped define a form of structure to an otherwise relaxed season.

However, the season wasn't without its faults. Some sketches, such as episode ten's 'Making the Band' and 'Kneehigh Park' skits and several of episode eleven's 'Failed Sketches' fell a bit flat and weren't as funny as the rest of the season. Thankfully, however, Chappelle's Show's faults weren't quite as pronounced as its previous season - which minimized the damage to the overall season as a whole.

As always, Chappelle's Show hosted a series of musical performances at the end of most of its episodes in the first season. This season is no different - as Dave Chappelle welcomes John Mayer, Anthony Hamilton, Common, Kanye West, Eryka Badu, Wyclef Jean, Snoop Dogg and Q-Tip to perform in pre-recorded segments to close out over half of the season's thirteen episodes. Mos Def also returns to perform as well in episode eleven along with Kanye West.

Most notably, however, is that some of the guest artists actually take part in some of the sketches during this season. Mos Def takes part in episode one's 'Racial Draft' sketch, episode eleven's 'Def Comedy Jam' skit and episode thirteen's 'Black Bush' parody. Snoop Dogg guest stars in episode ten's 'Kneehigh Park' skit, John Mayer appears and performs in episode three's 'Dancing People' sketch and Wu-Tang Clan also guest star in episode one's 'Racial Draft' segment.

Even more notable is the amount of guest appearances during season two of Chappelle's Show - as there are famous celebrities such as Arsenio Hall, Anthony Anderson, Jamie Foxx, Lil' Jon, Rick James, Eddie Griffin and Wayne Brady to name a few. Such an elaborate cast of guest artists and performers only further reinforce the ambition and transition of Chappelle's Show in its second season - attempting to scale ever higher in its quest for commerical success and critical acclaim.

The Black Tony Blair, played by Jamie Foxx in a guest star role during the Black Bush sketch. Image copyright of Comedy Partners.
The Black Tony Blair, played by Jamie Foxx in a guest star role during the Black Bush sketch. Image copyright of Comedy Partners.


Overall, the second season of Chappelle's Show manages to surpass its precursor in almost every way - not only in regards to its ratio of successful and memorable sketches but also in its musical line-up and guest stars. Dave Chappelle and the rest of the team have learned from the few rare hiccups of the first season and built up a true gem of a season.

In regards to its final mark, I've awarded season two of Chappelle's Show a solid 9 out of 10. Season two improved the quality and substance of the series in practically every way and thus is deserving of a better grade. Whilst there were a few sketches that fell flat, I felt that the creative team had learned from the previous season's mistakes and minimized the frequency of bad skits to an appropriate level.

With season one laying the foundation of the series and season two fortifying its stance in the comedy arena, it seemed that Chappelle's Show would only continue to build up from here. However, the strains of success and executive interference would cause the series to go on a hiatus - one that would see the show take a two-year absence, returning in 2006 for its third season.

4 stars for Chappelle's Show ~ Season 2

© 2017 Teashade Benu


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    • Teashade Benu profile imageAUTHOR

      Teashade Benu 

      2 years ago from Australia

      I know right? It's a shame the third season didn't quite last as long as the other two.

    • Angel Guzman profile image

      Angel Guzman 

      2 years ago from Joliet, Illinois

      I love Chappelle's Show! Too bad it came and went so fast!!


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