A Few Dream Interviews

In my last post, I described the desire to watch (or listen to) an interview between Dick Cavett and Dr. Atul Gawande. As an exercise, I wanted to see if it would make my list of interviews that will never happen but I would love to hear.

To set some parameters for list design:

• Each interview must have, at least, one person who generally interviews others and have no more than 2 parties.
  • The conversation does not need to be strictly host and guest format, but having an interviewer and interviewee helps set structure.
  • Bands, groups, and teams could comprise a single party.
• I must be reasonably sure that both parties are interesting in conversation, not just interesting people.
  • Jeff Bezos, Tim Cook, Elon Musk, are examples that fall into this category for me.
• The interview should not be political in nature.
  • e.g. the Trumps, Obamas, Bidens, Clintons, and Condoleezza Rice are excluded.
• I must be reasonably sure that the interview will never happen.
  • Joe Rogan and Oprah are excluded from being interviewers because they are likely willing and able to interview anyone.
• All parties must be living, physically capable of conversation, and speak the same language.

With the constraints in mind, the proposed conversation between Atul Gawande and Dick Cavett certainly makes my list. Here are a few others that did as well:

Tyler Cowen interviewing John Green:

• Who are they?
  • Tyler Cowen is an economist and writes the blog Marginal Revolution with Alex Tabarrok.
  • John Green is an author, podcaster, and vlogger.
• Why would it be interesting?
  • Tyler Cowen’s signature interview segment is “overrated or underrated,” where he asks his interviewees wither a series of concepts or items are over- or underrated. John Green’s podcast, the Anthropocene Reviewed, rates aspects of the human experience.
  • Tyler Cowen has an incredibly adversarial interview style, John Green is very sentimental. Both are well versed in a wide range of subjects. I imagine that the conversation will center on reviews of their shared experiences, from opposite vantage points and approaches.
• Why wont it happen?
  • Tyler Cowen tends to interview titans with strongly held beliefs in the technology, economics, progress-studies fields. John Green is not in any of them, and I am not sure that the interview would benefit either professionally.

Pardon My Take interviewing Sheryl Sandberg:

• Who are they?
  • Sheryl Sandberg is the Chief Operating Officer of Facebook and founder of LeanIn.org.
  • Pardon My Take (PMT) is the team, of Dan Katz and PFT Commenter, that produces an eponymous sports/satire podcast for Barstool Sports.
• Why would it be interesting?
  • Sheryl Sandberg is an inspiration for young leaders, specifically women, and for those grieving. She frequently speaks to women’s forums, elite institutions of higher learning, and writes for educated audiences. Pardon My Take has the most popular sports podcast and, almost exclusively, engages with the 18-35 male demographic. In order to confront toxic masculinity in the workplace, Sandberg’s message needs to meet that audience where it is comfortable.
  • Pardon My Take tends to make comedy for young men that are interested in sports. The hosts generally keep the conversation light, but are capable of serious topics (they had Dr. Fauci on to stress the importance of safe practices during COVID) and understand when to joke and when to let a guest speak. More than other platforms that target young men, these hosts are willing expand the horizon of their show (they did a series on Dungeons and Dragons) beyond what their audience thinks will be “cool.”
• Why wont it happen?
  • I could not find a video where Sandberg engaged with popular culture and cannot imagine her sitting for jokes at Barstool sports.

Ross Douthat interviews Christopher Moore:

• Who are they?
  • Christopher Moore is a comedic author.
  • Ross Douthat is a blogger, author, columnist, and conservative political analyst with a strong focus on religion.
• Why would it be interesting?
  • I imagine the conversation would start with Moore’s Lamb and how to think about Christ’s story. From that launching point, the conversation may meander to colors, progress studies, the need for religion, or the human condition. I would love to hear the conversation progress. Douthat’s most recent book The Decadent Society argues that the West is now in a decadent phase, the phase that commonly precedes catastrophe. Would Moore agree?
• Why wont it happen?
  • Neither Moore nor Douthat appear to seek popular interview channels. I don’t know that most Moore readers also read Douthat and vice versa.

Other notable proposed interviews:

Melissa Murray interviewing Tom Scott, Mike Duncan interviewing Jeffrey Morgenthaler, Tim Ferris interviewing James May (too likely?), and Malcolm Gladwell interviewing Dan Harmon (too likely?).