The Jann Arden Podcast

This week, Jann welcomes special guest Jessi Cruickshank, a multi-talented Canadian comedian and podcaster. They discuss the evolution of women in comedy and television looking back at Jessi's time hosting on MTV. They also touch on pop culture, parenting lessons, and dreaming big, with great advice for aspiring entertainers and content creators along the way.

More About Jessi Cruickshank

Jessi was born in Calgary in 1982 but moved to Vancouver at five years old. She did improv in high school alongside names like Seth Rogen and Nathan Fielder and moved to Toronto to attend U of T and set her sights on becoming a VJ. She eventually landed at MTV where she co-hosted The Hills: After Show with Dan Levy.

From there, Jessi went on to host everything from Canada’s Smartest Person to major live events like the Junos. In recent years, she’s built a huge following online with her sharp, very honest take on motherhood, especially after having twins, which led to her hit digital series New Mom, Who Dis? and now her pop-culture podcast Phone A Friend, which frequently tops the comedy charts in Canada. 

She’s on to promote Evening Club tour: a dance party designed for women and queer folks who want a great night out without sacrificing the next day. 

https://www.jessicruickshank.com/

https://feeds.acast.com/public/shows/phone-a-friend

Chapters:

(00:00) Welcoming Jessi Cruickshank: A Multi-Talented Guest

(04:42) The Evolution of Women in Comedy

(09:31) Creating Safe Spaces: Evening Club Dance Parties

(10:49) The Impact of Pop Culture and Reality TV

(18:39) The Success of Phone a Friend Podcast

(23:45) Navigating Celebrity Culture and Personal Opinions

(27:33) Navigating Power Dynamics in Comedy

(28:47) Reflecting on Personal Growth and Past Experiences

(32:19) The Influence of Family on Career Choices

(41:46) Advice for Aspiring Creatives
Learn more about your ad choices. Visit megaphone.fm/adchoices

This week, it's just Jann, Caitlin & Sarah! They discuss their April Fools' prank (sorry not sorry), the recent Juno Awards celebrating Canadian music, the rise of Indigenous artists like William Prince, the evolution of the Junos, and the celebration of Canadian talent like Sarah McLachlan, Joni Mitchell, Nelly Furtado and more. This week on The Scroll , Caitlin highlights the significance of the upcoming Artemis mission and space exploration and the three get back to CANCON conversation touching on the career longevity of Celine Dion as fans register to purchase tickets for her upcoming Paris shows!

Chapters:

(00:00) April Fools' Day Shenanigans

(06:03) The Art of Pranking

(12:59) The Juno Awards and Canadian Music

(18:49) Space Exploration and the Artemis Mission

(18:57) The Evolution of Music Technology

(19:32) Celebrating Canadian Music Icons

(20:03) The Juno Awards and Industry Dynamics

(21:09) The Importance of Artist Engagement

(22:26) Memorable Moments from the Junos

(24:34) The Subjectivity of Music Awards

(25:32) Canada's Impact on Global Music

(27:09) The Role of Canadian Artists in the Industry

(29:14) Reflections on Career Longevity in Music

(30:50) Celine Dion's Comeback and Legacy

(36:24) Gala Stories and Musical Connections

(39:01) Indigenous Music in Canada

(42:00) Patreon Teaser

#ASKJANN - want some life advice from Jann? Send in a story with a DM or on our website.

Leave us a voicenote!

⁠www.jannardenpod.com/voicemail/⁠⁠

Get access to bonus content and more on Patreon:

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠www.patreon.com/JannArdenPod⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Connect with us:

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠www.jannardenpod.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠www.instagram.com/jannardenpod⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠www.facebook.com/jannardenpod

Learn more about your ad choices. Visit megaphone.fm/adchoices

To start the show, Jann Arden, Caitlin Green, and Sarah Burke share exciting news about their upcoming live podcast taping in Toronto on May 5th as part of the Departure Festival + Conference — a multi-day celebration of music, film, and media, the first week of May in Toronto.

🎙️ Live Podcast Recording 🗓️ May 5, 2026

📍 Jane Mallett Theatre | St. Lawrence Centre for the Arts

ON SALE NOW! https://www.ticketmaster.ca/event/10006474E4535C04

They also share personal updates, including Caitlin's unfortunate experience with identity theft and Sarah discovering some fraud during tax season. During The Scroll, Caitlin explains the Taylor Frankie Paul saga and the implications for the Bachelorette franchise and the idea of living on a 15-year cruise ...would you?

Special guest Kate Bowler returns for the second half of the show to promote her book Joyful, Anyway! The Canadian (Winnipeg-born), bestselling author, Duke University Professor and the host of Everything Happens podcast discusses the cultural pressures surrounding happiness.

Grab Kate's new book:

https://www.penguinrandomhouse.com/books/764086/joyful-anyway-by-kate-bowler/

More About Kate and her work:

https://katebowler.com/

#ASKJANN - want some life advice from Jann? Send in a story with a DM or on our website.

Leave us a voicenote!

⁠www.jannardenpod.com/voicemail/⁠⁠

Get access to bonus content and more on Patreon:

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠www.patreon.com/JannArdenPod⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Connect with us:

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠www.jannardenpod.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠www.instagram.com/jannardenpod⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠www.facebook.com/jannardenpod
Learn more about your ad choices. Visit megaphone.fm/adchoices

Get tickets to our live show in Toronto at Departure! OnlyJanns get a discount and presale TODAY ONLY (Wednesday March 25th, 2026 at 10am EST). On-sale to general public Friday March 27th at 10am EST.

In honour of Juno Awards celebrating Canadian music coast to coast this weekend, we re-visit our conversation with legendary singer-songwriter Sarah McLachlan who's nominated for Better Broken. She talks about her new album and the Lilith Fair documentary while sharing how she balances her life as a musician, mother, and humanitarian.

More about Sarah McLachlan:

3X GRAMMY Award winner and global phenomenon Sarah McLachlan recently announced Better Broken, her first album of new material in over a decade (and studio album #10), due out September 19 via Concord Records.

Lilith Fair: Building a Mystery Documentary is directed by Ally Pankiw, and produced by Dan Levy’s Not A Real Production Company.

⁠Watch the “Better Broken” music video HERE. ⁠

⁠https://www.sarahmclachlan.com/⁠

*⁠Photo Credit Kharen Hill*⁠
Learn more about your ad choices. Visit megaphone.fm/adchoices

Jann, Caitlin & Sarah reunite without a guest. Jann tells stories of the bear in her yard, Caitlin catches everyone up on her house-hunting challenges, and Sarah talks about her birthday week! Jann also tells her co-hosts about a freak-accident with a knife, and we'll remind you JANN IS NOT A DOCTOR :)

Caitlin catches us up on The Oscars and some big changes coming to daytime television. Jann and Sarah chat about some disturbing AI advancements and consider the future of the music industry while celebrating the first week of Spring!

Stay tuned for a BIG announcement next week if you want to join us in the audience at our next live show!

Get access to bonus content, first dibbs on tickets to our live show and more on Patreon:

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠www.patreon.com/JannArdenPod⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

#ASKJANN - want some life advice from Jann? Send in a story with a DM or on our website.

Leave us a voicenote!

⁠⁠www.jannardenpod.com/voicemail/⁠⁠⁠

Connect with us:

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠www.jannardenpod.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠www.instagram.com/jannardenpod⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠www.facebook.com/jannardenpod
Learn more about your ad choices. Visit megaphone.fm/adchoices