Conversations with Comedians

I am a collector. I love collecting conversations. To me, they are ‘breaths of fresh air’, my go-to when I need some emotional and psychological stimulation to get me to be both introspective about my life, and observational about my surrounding.

Over the years, I’ve collected a nice playlist of conversations that continue to generate ideas in my mind every time I listen to them. These conversations are thoughtful, witty, informative, and help broaden my worldview.

In this post, I want to share two conversations in my collection which involves two comedians from two generations: Dave Chappelle and Hassan Minhaj.

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#1 Iconoclast: Season 2 Episode 6.

The first conversation was an episode of a tv series called Iconoclast that I caught on YouTube.

Iconoclast was a television series that showcase a couple of “creative visionaries” who discuss and share their thoughts on life, and their craft. The series was aired from 2005 to 2012 on Sundance TV where various well-known actor, musician, film producer, journalist, chef, sportsman, dancer, and writer were among individuals paired up for each episode. There were 6 episodes per season and the show latest for 6 seasons.

In 2006, Dave Chappelle, the comedian, actor, producer sat down with the poet, writer, activist Maya Angelou for season 2 episode 6 of the Iconoclast, which was aired on November 30, 2006. The episode is also available on YouTube at this link.

In their conversation, Dave and Maya discussed a range of issues including how they each approached their craft, as ‘pop-culture figures.’ Iconoclast, as Maya informs Dave, means ‘to break up the icon…the figure held high by the majority.’ In a society governed by icon ‘worshipping’, the idea that these icons can be ‘broken up’ must appear radical.

They also discussed the fundamental difference between them as artists. Maya as a poet, novelist, writer, needs solitude to create her works. Dave, as a stand-up comedian, on the other hand, needs an audience to create his art. As Dave says, ‘sometimes inspirations won’t hit you until you’re in front of the people.’

As a writer, I see the strength in both processes. There are times when being alone is necessary to write, yet to quote Dave, ‘I can’t write in a vacuum.’ Engagements with others, in any form available, may help facilitate the further mastery of your craft. You decide what works.

They also shared insights into how valuable words are, and when used strategically, words can both hurt and heal a person and a nation. Writing that is informed by emotions such as anger may help purge the writer from ‘the bitterness’ one experiences in life. Writing to both of them is ‘cathartic.’ I share this sentiment.

Writing has the power to help the writer make sense of what’s going on in her mind and heart, and once these thoughts and emotions are constructed and articulated, they leave the writer with a sense of acceptance of that experience.

#2 Homeroom with Sal Khan.

The second conversation was streamed on YouTube on a channel that I subscribe to, Khan Academy.

Homeroom with Sal is a conversational series that Sal Khan of Khan Academy conducted since schools both in America and many parts of the world had to be closed due to the worldwide Covid-19 pandemic this year. The interviews were streamed on YouTube and Facebook.

On 30 July 2020, Sal streamed his conversation with Hassan Minhaj, the comedian, writer, producer. One of the best take away from the conversation was how to know your ‘talent’, and more importantly, how to nurture that talent despite the lack of support from your family and community.

Hassan shares the struggles of breaking free from the Desi or ‘the south Asian diasporic’ community’s focus on particular professions which include doctor, engineer, or lawyer, towards becoming a comedian. Despite attempts at pre-med and pre-law, it was his innate talents of public speaking, debate, and cracking jokes that allowed him to discover his passion for comedy. I appreciate this statement by Hassan about how comedy serves him, ‘I use comedy as an art form to understand myself.’

As he says, ‘Society doesn't necessarily value them, [the Desi] community definitely didn't value them, but I found value in them.’

His advice on how to identify your talents and what to do when you have discovered them is worth quoting:

“Write down what are your gifts. Meaning what are the things you do well, even if you rolled out of bed you would be better than anyone in your class. …What is that natural alacrity that you have where you are better than everybody…The key is figuring out what your gifts are and applying work ethic to that.”

I think that’s great advice be it for someone graduating high school and searching for a path, or someone entering middle age and seeking greater fulfillment in life. We all need to discover our gifts and ‘apply work ethic’ to further develop them, and see where these gifts lead us.

We all have a ‘take and perspective’ on life that is colored by our upbringing, lifestyle, and personality. Imagine being able to use our ‘take and perspective’ on life in our chosen craft and making a career out of it. That’s what comedians do best, I think.

As these two conversations illustrate, there is more to comedians than just cracking jokes. Dave Chappelle and Hassan Minhaj represent two comedians from different generations who are intelligent, articulate and are able to present us their interesting perspectives through wit and humor.

Based on these conversations, what is the essence of comedy? Hassan captures it well when he says, “Great jokes at their essence are great philosophical positions said in a funny way.”



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Raihanah M.M.

Educationist with a love for stories that can change the world for the better.