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She’s That Lesbian: Maggie Cassella on Comedy, Queer Legacy, and Laughing Through It All
What do you get when you mix an ex-lawyer, queer icon, stand-up comic, political satirist, and accidental contractor? You get Maggie Cassella.
In this unforgettable Pride Month episode of A Life Worth Being, Sue reconnects with her longtime friend Maggie Cassella—a powerhouse queer comedian, writer, producer, and self-described jill-of-all-trades. From bartending at one of Hartford’s first lesbian bars to launching North America's first queer comedy festival, Maggie’s done it all—and she has the stories to prove it.
✨ In this laugh-out-loud conversation, Maggie talks about:
Going from the courtroom to the comedy stage (thanks to a dare from Lea DeLaria)
Producing the first all-queer comedy fest We're Funny That Way
Lessons from decades of queer visibility and activism
The real deal on jealousy, legacy, and making space for the next generation
Her new work in film, TV writing, and the viral-ready jingle "She’s That Lesbian"
She also shares what it means to use humor as healing, and why kindness—more than fame—is the legacy that really matters.
📍 Maggie’s Website: https://maggiecassella.com/
🌈 Learn more at: https://werefunnythatway.com/
🎁 Support LGBTQ2S+ causes: https://rainbowcharitynetwork.org/
FOLLOW and CONNECT
Website - https://www.willoughbycoaching.com/
Facebook - https://www.facebook.com/willoughbycoaching/
Instagram - https://www.instagram.com/sue_willoughby/
Linkedin - https://www.linkedin.com/in/suewilloughby/
Thanks to my amazing Producer and Editor Jess Grace Garcia (they/them) of Springwood Productions.
https://www.springwoodproductions.com/
[00:00:00] - Podcast Anniversary & Introduction
[00:01:02] - Early Memories and Friendship Stories
[00:08:07] - Maggie Casella’s Career Journey
[00:11:22] - Comedy, Identity, and Evolving as a Comic
[00:21:15] - Creative Projects and Current Work
[00:29:03] - Mentoring, Ego, and Supporting Other Comics
[00:45:07] - Kindness and Personal Legacy
[00:53:13] - Outro and Resources
If you want to start your own podcast feel free to reach out to us. Jess and I would love to help you on your journey to sharing your story and passion.
#LifeWorthBeing #Transformation #LifeCoach #Women #Empowerment #PersonalGrowth #InnerStrength #PurposefulLiving #MidlifeTransformation #Mindfulness #Mindset #SelfDiscovery #WomenEmpowerment #Midlifestrategies
Thank you for watching! If you're seeking more insights on living a truly meaningful and fulfilling life, be sure to subscribe to my channel. And don’t forget to hit the bell icon so you never miss an update!
An extraordinary life starts within. Discover your inner strength and awaken a life worth being through experiential, equine-assisted life coaching. Welcome to My Universe!
I am Sue Willoughby, transformational life coach & host of A Life Worth Being—a podcast that dives deep to help you uncover the true meaning of a fulfilling life. This channel is here to inspire and empower women over 40 to step into their fullest potential, break through limitations, and truly thrive.
Each week, we bring you powerful video podcasts filled with real-life stories of transformation, resilience, and courage. Expect raw, heart-centered conversations and life-changing insights designed to help you break boundaries and start crafting a life brimming with purpose, joy, and passion. This is more than just a channel; it’s a community.
Join me to explore, grow, & connect with like-minded women on the journey to creating a life worth being. Subscribe now and let’s awaken your limitless potential together!
View all episodes
By Sue WilloughbyWhat do you get when you mix an ex-lawyer, queer icon, stand-up comic, political satirist, and accidental contractor? You get Maggie Cassella.
In this unforgettable Pride Month episode of A Life Worth Being, Sue reconnects with her longtime friend Maggie Cassella—a powerhouse queer comedian, writer, producer, and self-described jill-of-all-trades. From bartending at one of Hartford’s first lesbian bars to launching North America's first queer comedy festival, Maggie’s done it all—and she has the stories to prove it.
✨ In this laugh-out-loud conversation, Maggie talks about:
Going from the courtroom to the comedy stage (thanks to a dare from Lea DeLaria)
Producing the first all-queer comedy fest We're Funny That Way
Lessons from decades of queer visibility and activism
The real deal on jealousy, legacy, and making space for the next generation
Her new work in film, TV writing, and the viral-ready jingle "She’s That Lesbian"
She also shares what it means to use humor as healing, and why kindness—more than fame—is the legacy that really matters.
📍 Maggie’s Website: https://maggiecassella.com/
🌈 Learn more at: https://werefunnythatway.com/
🎁 Support LGBTQ2S+ causes: https://rainbowcharitynetwork.org/
FOLLOW and CONNECT
Website - https://www.willoughbycoaching.com/
Facebook - https://www.facebook.com/willoughbycoaching/
Instagram - https://www.instagram.com/sue_willoughby/
Linkedin - https://www.linkedin.com/in/suewilloughby/
Thanks to my amazing Producer and Editor Jess Grace Garcia (they/them) of Springwood Productions.
https://www.springwoodproductions.com/
[00:00:00] - Podcast Anniversary & Introduction
[00:01:02] - Early Memories and Friendship Stories
[00:08:07] - Maggie Casella’s Career Journey
[00:11:22] - Comedy, Identity, and Evolving as a Comic
[00:21:15] - Creative Projects and Current Work
[00:29:03] - Mentoring, Ego, and Supporting Other Comics
[00:45:07] - Kindness and Personal Legacy
[00:53:13] - Outro and Resources
If you want to start your own podcast feel free to reach out to us. Jess and I would love to help you on your journey to sharing your story and passion.
#LifeWorthBeing #Transformation #LifeCoach #Women #Empowerment #PersonalGrowth #InnerStrength #PurposefulLiving #MidlifeTransformation #Mindfulness #Mindset #SelfDiscovery #WomenEmpowerment #Midlifestrategies
Thank you for watching! If you're seeking more insights on living a truly meaningful and fulfilling life, be sure to subscribe to my channel. And don’t forget to hit the bell icon so you never miss an update!
An extraordinary life starts within. Discover your inner strength and awaken a life worth being through experiential, equine-assisted life coaching. Welcome to My Universe!
I am Sue Willoughby, transformational life coach & host of A Life Worth Being—a podcast that dives deep to help you uncover the true meaning of a fulfilling life. This channel is here to inspire and empower women over 40 to step into their fullest potential, break through limitations, and truly thrive.
Each week, we bring you powerful video podcasts filled with real-life stories of transformation, resilience, and courage. Expect raw, heart-centered conversations and life-changing insights designed to help you break boundaries and start crafting a life brimming with purpose, joy, and passion. This is more than just a channel; it’s a community.
Join me to explore, grow, & connect with like-minded women on the journey to creating a life worth being. Subscribe now and let’s awaken your limitless potential together!