When Roasts Stop Being Funny

LISTENER QUESTIONS AND ENTERTAINMENT INSIDER SECRETS

Richard Crouse and Sarah Hanlon open the Entertainment Is Broken mailbag to answer listener questions about the strange machinery behind show business. Richard shares what celebrity junkets are really like, from exhausted movie stars answering the same question 40 times in a day to memorable encounters with Meryl Streep, Madonna, and Bill Murray. Sarah breaks down the reality TV machine from her own experience on Big Brother Canada, explaining what feels real, what gets shaped, and why pressure can create drama without producers needing to fake it. Then they tackle the big one: if they could fix one thing about Hollywood or media, what would it be? The answer involves risk, weird movies, smaller budgets, and letting audiences miss things before the next franchise installment arrives.

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.