Back in April, the award-winning Canadian writer Ian Williams was named this year’s Massey lecturer. Since 1961, the Massey Lectures have invited distinguished writers, thinkers and scholars to present their ideas in a five-part lecture series across Canada. In this conversation with Tom Power, Ian tells us how to have better conversations with one another,  why it’s important to have difficult conversations even at the risk of offending people, and how listening can be a courageous thing to do.

Sean Baker (Tangerine, The Florida Project, Red Rocket) is an award-winning filmmaker whose work often explores the lives of people living on the fringes. His latest film, “Anora,” follows a sex worker who quits her job after a whirlwind romance with a Russian billionaire, but soon realizes her fairytale ending isn’t all she’d hoped. Sean joins Tom Power to tell us why this story spoke to him, how a Canadian sex worker’s memoir helped shape the film, and what it felt like to win the prestigious Palme d'Or at this year's Cannes Film Festival — a dream he’s had forever.

The Juno-winning Canadian jazz singer and pianist Laila Biali is back with a new album, “Wintersongs,” which was inspired by some time she spent in Banff. She says the album brings her back to her roots as a classical pianist — a path that was cut short after a car accident changed her life at 15. Laila sits down with Tom Power to talk about the record, how it blends different sides of herself, and a difficult new challenge she’s facing in both her life and music.

If you’ve ever thought it was too late for you to try something new, you should listen to Sindhu Vee. She’s one of the most talked-about comics in the U.K. right now, but just a few years ago, she was an investment banker who was trying to figure out what to do with her life after having kids. Sindhu joins Tom Power to tell us how she got her start in comedy without ever having seen a live stand-up show, the strange similarities between investment banking and what she does now, and what attracted her to her new series, “The Pradeeps of Pittsburgh.”

The Canadian acting legend Saul Rubinek has returned to the stage to explore one of theatre’s most controversial characters: Shylock, the Jewish moneylender in Shakespeare’s comedy “The Merchant of Venice.” Saul stars as a fictionalized version of himself in Canadian Stage’s new production of “Playing Shylock,” which takes a poignant yet comedic look at cancel culture, representation and anti-Semitism. But for Saul, it’s about more than that — it’s about keeping an audience “off balance.” He sits down with Tom Power to talk about the play, and how “Q” actually ended up influencing the production.

When the award-winning author Jason Reynolds was visiting a juvenile detention centre, he asked what kind of books young boys checked out the most. The answer really surprised him: romance novels. Jason realized that young men have a real hunger to learn about love, sensitivity and intimacy. That sparked the idea for his latest book, "Twenty-Four Seconds from Now,” which follows a Black teen boy who’s about to have sex with his girlfriend for the first time. Jason joins Tom Power to talk about the book and how he’s writing the stories he wishes he had growing up.

One of the most famous tenors in the world, Andrea Bocelli, is celebrating three decades in music. In addition to a concert film and a new album called “Duets,” he’s the subject of a new documentary about his life, “Because I Believe.” It traces his journey from a rural farming village in Tuscany to sold-out stadium concerts with tens of thousands of fans. Andrea joins Tom Power to discuss his journey, including how Luciano Pavarotti helped launch his career, his special friendship with Celine Dion, and which singers he looks up to the most.

After signing a major recording contract at age 12, Joanna "JoJo" Levesque shot to the top of the pop charts with hits like “Leave (Get Out)” and “Too Little, Too Late.” She was on track to become one of the biggest pop singers of the 2000s — and then she seemingly disappeared overnight. In this interview with Tom Power, JoJo opens up about the betrayals she endured as a child star, the label issues that derailed her promising career, and why she’s telling her story now in a new memoir called “Over the Influence.”

The Canadian rapper, singer-songwriter and producer k-os is kind of like the Forrest Gump of popular music — he’s been everywhere. On the 20th anniversary of his smash hit album “Joyful Rebellion,” k-os sits down with Tom Power to share some wild stories from his life and career, like the time he hung out with Prince and how he has Shaquille O'Neal to thank for his first hit in the U.S.

A few years ago, the musician Tia Wood moved to Los Angeles from her home of Saddle Lake Cree Nation in Alberta. Though she comes from a musical family (her mom is in a drum group, her sister is a Juno winner, and her dad is a founder of the award-winning group Northern Cree), Tia has managed to find her own sound. Now, she’s the first Indigenous woman to be signed to Sony Music Canada, and she’s just released her debut EP, “Pretty Red Bird.” She sits down with Tom Power to set up a song from the record.