Entertainment Is Broken

Is Late Night TV Dying? Colbert, Letterman & Canada’s Talk Show Problem

Is late night television dying, or has it just been chopped up into clips, podcasts, TikToks, and celebrity interviews designed for the algorithm? This week on Entertainment Is Broken, Richard Crouse and Sarah Hanlon look at the past, present, and uncertain future of late night TV. Sparked by conversation around Stephen Colbert, they trace the format from Johnny Carson to David Letterman, Conan, Kimmel, Fallon, Colbert, and Canada’s own attempts to build a proper talk-show tradition. Richard reflects on hosting Pop Life, his bar-set talk show on CTV, and why there is still value in long-form, relaxed, curious conversation on television. Sarah makes the case that Canada needs more talk and variety shows ... not just for entertainment, but as part of a real star-making system. They also discuss Obsessed, Indie Navarette’s standout performance, Keke Palmer, Boots Riley’s I Love Boosters, and why smaller, stranger movies may be finding their way back into theatres.

When Roasts Stop Being Funny

Richard Crouse and Sarah Hanlon take on comedy as an art form… and why it so often gets treated like drama’s unserious cousin. They discuss the craft behind great comedy, from timing and rhythm to improv, physical performance, writing, surprise, and the invisible work that makes a joke land. They also dig into the Kevin Hart roast, modern roast culture, the difference between shock and surprise, and whether some comedy has become more about cruelty, grievance, and identity than actual jokes. Along the way: Kinky Boots, Mr. Dressup, Jim Carrey, Gary Shandling, the Comedy Cellar, the Joe Rogan comedy universe, and underrated comedy favourites including After Hours and I Love You to Death. Because if drama makes you cry, it’s art. But if comedy makes you laugh, somehow it still has to prove itself.

The Beatles or The Rolling Stones Forever

Mick Jagger is 82. Paul McCartney is 83. Ringo Starr is still making music. So are we witnessing a creative renaissance... or rock’s most determined refusal to retire? Richard Crouse and Sarah Hanlon discuss legacy artists, nostalgia, concert ticket prices, The Beatles, The Rolling Stones, Wings, Billy Preston, and why some performers become heritage acts while others keep creating. Plus, squirrels, Paul Rudd, and the strange magic of artists who never quite leave the stage.

Huge Star Tiny Room

What if the best concert you’ll ever see… only has 50 people in the room? This week on Entertainment Is Broken, Richard and Sarah explore the phenomenon of massive artists going small — from secret shows and fake band names to surprise appearances in tiny venues. Inspired by stories like The Rolling Stones at the El Mocambo and recent pop-up gigs from Olivia Rodrigo, they unpack why these intimate performances often feel more powerful than arena spectacles. Along the way, they share personal experiences, unforgettable moments with artists like Dr. John, and discuss what these small shows reveal about creativity, connection, and the true nature of performance. Because sometimes… stripping it all back is what makes it unforgettable.

Michael Jackson - Fact or Fiction

A new Michael Jackson biopic raises a familiar question… do audiences actually want the truth, or just a great show? This week, Richard Crouse and Sarah Hanlon unpack the new film Michael and the growing trend of biopics that trade accuracy for spectacle. When a story as complex as Michael Jackson’s gets streamlined into a crowd-pleasing concert experience, what gets lost… and does it even matter? They explore the art vs. artist debate, the power of nostalgia, and why some cultural icons remain untouchable—no matter how complicated their legacy becomes. It’s a conversation about storytelling, memory, and the uncomfortable space where fact and entertainment collide.