Podcast Summary: This Past Weekend w/ Theo Von – Episode E553: Grace O'Malley

Release Date: January 6, 2025

Introduction

In Episode E553 of This Past Weekend w/ Theo Von, host Theo Von welcomes Grace O'Malley, an emerging entertainer from the Boston and New England regions. Grace, known for her work with Barstool Sports and burgeoning stand-up comedy career, joins Theo to discuss her journey in comedy, personal anecdotes, relationships, and upcoming projects.

Guest Background

[06:36] Grace O'Malley shares her roots, originally hailing from the outskirts of Boston. She delves into her family dynamics, mentioning having three younger sisters and humorously referring to herself as "the milkman's" due to her red hair.

[08:08] Grace discusses the cultural shifts in her hometown, touching upon historical events like the busing controversy of the 1970s, which led her family to relocate outside Boston.

Stand-Up Comedy and Podcasting

[06:33] Grace recounts her move to New York in 2020, initially performing stand-up on the streets during the COVID-19 pandemic. She became serious about comedy in January 2024, intensifying her performances and networking efforts.

[07:17] Whitney Cummings played a pivotal role in Grace's career by inviting her to open for her tours, propelling Grace into larger venues.

[41:10] Grace expresses her passion for stand-up, emphasizing her desire to be recognized primarily for her comedy rather than other ventures. She highlights the challenges of perfecting her craft and finding her unique voice on stage.

Personal Anecdotes and Experiences

[10:14] Theo shares a personal mishap involving electrical circuits at a carnival, setting a humorous tone for their candid conversation.

[19:30] Grace humorously describes her father's near-death experience from electrocution, adding a light-hearted narrative to their discussion.

[58:47] Both hosts share stories about their encounters with celebrities and the humorous situations they've found themselves in while navigating the entertainment industry.

Friendship and Relationships

[32:54] Grace discusses her longstanding friendship with Brianna Chicken Fry, detailing their collaboration on the podcast "Plan Brie Uncut." Despite facing professional challenges and changes, their bond remains strong.

[21:11] The conversation shifts to personal relationships, with Grace candidly admitting she's never had a boyfriend. She humorously attributes her lack of romantic success to her "bro-like" flirting style.

[74:02] Grace opens up about her struggles with alcoholism, describing herself as a "functioning alcoholic" and her efforts to moderate her drinking habits through initiatives like Dry January.

Substance Use and Mental Health

[60:32] Grace shares her experiences with substance use, including a single instance of taking LSD and her family's grappling with mental health issues exacerbated by drug use.

[46:38] Theo and Grace discuss the impact of drugs on personal and professional lives, highlighting both the humorous and serious repercussions they've encountered.

New Year's Resolutions and Personal Growth

[100:38] Both Theo and Grace reflect on their New Year's resolutions. Grace aims to reduce her alcohol consumption, while Theo focuses on being more intentional with his time and relationships.

[45:40] They explore themes of honesty and authenticity in comedy, emphasizing the importance of being true to oneself both on and off the stage.

Upcoming Projects and Future Plans

[52:05] Theo reveals his collaboration with David Spade on a movie project, discussing the challenges of independent filmmaking and the joy of working with admired figures in the industry.

[95:25] Grace announces her upcoming podcast, "Disgraceful," set to release in February on the Unwell Network. The podcast features a unique format where guests audition to become her co-host, blending humor with creative collaboration.

Notable Quotes

• Theo Von [03:00]: "Being alive is just. Damn. It's a lot sometimes, you know, it just feels like a lot."

• Grace O'Malley [38:35]: "I finally found my thing."

• Grace O'Malley [26:20]: "I'll wait for my special day. I don't either. This."

• Theo Von [71:22]: "I would rip that left and right if I had the sex."

• Grace O'Malley [100:07]: "I'm trying to kick back."

Conclusion

Episode E553 of This Past Weekend w/ Theo Von offers an intimate glimpse into Grace O'Malley's life as she navigates the demanding worlds of stand-up comedy and podcasting. Through laughter, personal stories, and honest reflections, Theo and Grace create a relatable and engaging conversation that resonates with listeners. As Grace embarks on new projects like her podcast "Disgraceful," both hosts share their aspirations and challenges, highlighting the ever-evolving nature of personal and professional growth in the entertainment industry.

Note: Advertisements and non-content segments from the transcript have been excluded from this summary to maintain focus on the core conversation between Theo Von and Grace O'Malley.