What's Up Nation with Jessi Cruickshank

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. 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

You can listen to What's Up Nation with Jessi Cruickshank online on Radio and Podcast. Open the player on this page to stream the available audio.

What's Up Nation with Jessi Cruickshank is an episode from The Jann Arden Podcast by Jann Arden.

This episode is 46:06 long.

This episode was published on Apr 10, 2026.

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