What's Up Nation with Jessi Cruickshank

What's Up Nation with Jessi Cruickshank

April 10, 2026 · 46 min · Season 6 · Episode 15

About this episode

Jann Arden interviews Jessi Cruickshank about her career in comedy and television, discussing women's evolution in the industry and sharing insights for aspiring entertainers.

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…

People in this episode

Host: Jann Arden

Guest: Jessi Cruickshank

Topics covered

Keywords

Mentioned in this episode

Organizations: MTV, Canada’s Smartest Person, Evening Club, Phone A Friend

Places: Calgary, Vancouver, Toronto

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