Before making her name as a singer-songwriter, Jennifer Castle worked at a restaurant in Toronto with celebrity chef and restaurateur Matty Matheson. Now, nearly 20 years later, Matty is an executive producer and actor on the hit series “The Bear” and Jennifer has a song featured in the new season. She joins Tom to set up the song, titled “Blowing Kisses.”

Ten years after immigrating to Canada from India, the rapper and singer Karan Aujla made history as the first Punjabi artist to ever win a Juno Award. But he was a global superstar well before then, topping the charts with his blend of Punjabi music over hip-hop and trap beats. Now, Karan is the latest Global Apple Music Up Next Artist, which makes him the first Punjabi artist to join the initiative geared towards identifying, showcasing and elevating rising talent. Karan talks to Tom about why Canada is a hub for Punjabi hip-hop, and the childhood losses that pushed him towards songwriting.

Jodie Comer is an Emmy and Tony Award-winning actor who you may know as the assassin Villanelle on the show “Killing Eve.” Though she’s been acting since childhood, Jodie treats every role with the intense work ethic of someone who’s still gunning for their big break. In her new film, “The Bikeriders,” she stars opposite Austin Butler, Tom Hardy and Michael Shannon as a woman who married into a biker gang. The film was inspired by an actual Midwestern motorcycle club that started in the ‘60s. Jodie joins Tom to talk about the film, learning a new accent for the project, and the incredible work ethic that’s gotten her this far in her acting career.

The Canadian director Brendan Healy has taken on an epic project: a new production of Matthew López's seven-hour play “The Inheritance,” which has been called the most important play of the 21st century. Brendan sits down with Tom to tell us how the play represents a conversation between generations of gay men, what happens when you don't learn about the past, and how that conversation played out in real life at rehearsals.

The Canadian musician Jamie Fine first found success with the duo Elijah Woods x Jamie Fine after they won the singing competition show “The Launch” in 2018. But after realizing something wasn’t sitting right with her, Jamie decided to start fresh with a solo career. Now, she’s released her sophomore EP, “if this is it.” Jamie sits down with Tom to share some hard-earned wisdom from her journey in music, why she wishes it took longer for her to have found success, and how she became a superstar in South Africa.

You might know E.R. Fightmaster from their groundbreaking role as Dr. Kai Bartley on “Grey's Anatomy” or you may be familiar with their music. Earlier this month, the actor and musician released their second EP, “Bloodshed Baby” under their stage name Fightmaster. E.R. joins Tom to set up a song off the record and shares what it was like being cast as the first non-binary doctor on “Grey's Anatomy.”

Last year was a big one for Gracie Abrams. The singer-songwriter released her debut album, got nominated for best new artist at the Grammys, and opened for Taylor Swift on the Eras Tour. Now, she’s released her sophomore album, “The Secret of Us,” which she co-wrote with her best friend. Gracie joins Tom in studio to talk about the record, getting over her fear of performing, and what it’s like working with Taylor.

The Montreal singer-songwriter Dominique Fils-Aimé is back with a new single, “Moi je t'aime.” It’s the Juno-winning artist’s first song in French, despite French being her first language. Dominique joins Tom to set up the track and explain what singing in French gives her as an artist.

Dr. Shirley Cheechoo is one of Canada’s most prominent voices in Indigenous film and theatre. At this year’s annual Weengushk International Film Festival, Dr. Cheechoo is giving back to her community with a special event called Blanket of Stars: A Tribute to Resilience, which is dedicated to Canada’s residential school survivors — or as she calls them, residential school warriors. Dr. Cheechoo joins Tom to talk about her life on stage and screen, and what art can and can’t do when it comes to healing.

The legendary Canadian actor Donald Sutherland has died at age 88. Over the course of his six-decade career, he was in more than 150 films and TV series, and more recently he was honoured with his very own Canadian stamp. Today, we revisit Tom’s conversation with Donald about his stamp, his early days as an actor, and why he didn’t want dual Canadian and American citizenship.