Has our culture had a grown-up conversation yet about race and gender? Or did the media flip from the casual bigotry of the 20th century to the censorious hysteria of the 2010s in a way that empowered the rise of the New Right? And what was it like to work as a comedy writer on a hit progressive comedy show as the culture underwent The Great Awokening?

Jeff Maurer was a writer on Last Week Tonight with John Oliver for its first six seasons. He left in 2020 after feeling its editorial angle had become too ideologically captured. Now, Jeff has a wildly popular political-satire Substack, “I Might Be Wrong”.

Josh intended to chat with Jeff to help make sense of Minneapolis, Epstein, ICE, the 2020 election ballots, Don Lemon’s arrest and, of course, the Melania documentary. There’s been a lot, lately. But this conversation evolved into a far more fascinating and funny discussion about what the controversies over blackface and transgenderism can teach us about how the media lost its way; about whether we’ve lost the ability to cover the news - and to satirise it - without preaching to the choir.

Follow Jeff’s comedy writing below at www.imightbewrong.org