Podcast Summary: "Sandler's Sons: Ethan Cutkosky and Conor Sherry" – Disgraceful with Grace O'Malley

Release Date: July 31, 2025

Introduction of Guests

In this episode of Disgraceful with Grace O’Malley, host Grace welcomes her first duo guest stars, Ethan Cutkosky and Conor Sherry, who are auditioning to become her co-hosts. Grace humorously navigates the challenge of correctly pronouncing their full names, setting a light-hearted tone for the episode.

Grace O. Ali [01:24]: "Welcome in. Connor and Ethan. I just skipped the last names. That's what I ended up doing."

Movie Premieres and First Impressions

The conversation kicks off with discussions about attending premieres. Both Ethan and Conor share their experiences attending the premiere of "Happy Gilmore 2," where Grace humorously recounts her awkward interaction on the red carpet.

Grace O. Ali [01:57]: "I wish I just said, hi, guys. How you."

Ethan jokes about regretting his initial attempt to make small talk, leading into a nostalgic reflection on meeting Grace at an SNL after-party and crossing paths multiple times before the premiere.

Ethan [02:42]: "John Daly's the real method actor."

"Most Likely To" Game Segment

Grace introduces the popular segment "Most Likely To," where she poses humorous scenarios to determine which guest is more prone to certain actions. This segment reveals the playful dynamics between Ethan and Conor.

1. Forgetting Lines in Improv

   • Conor [05:20]: "I think it would be me."
   • Both guests humorously admit to occasionally blanking out during performances.

2. Stealing Happy's Flasks

   • Conor [05:55]: "Yeah, we probably both do it."
   • They laugh about the fictional flasks from "Happy Gilmore" and their intentions to use them.

3. Going Ghost Mode (Turning Off Location Sharing)

   • Ethan [07:01]: "I turn it off so often..."
   • The discussion shifts to the quirks of modern technology and personal boundaries.

4. Having Burner Accounts on Instagram

   • Conor [09:37]: "I think I have a few."
   • They delve into the playful deceit of maintaining anonymous social media profiles.

5. Getting a Hole in One (Golf Edition)

   • Ethan [12:38]: "I feel like it would be me only."
   • The guests share their varying degrees of golfing prowess, intertwining humor with personal anecdotes.

6. Getting into Physical Fights

   • Connor [13:52]: "I'm going to be physical if it takes it."
   • A candid and comedic exploration of their temperaments and past altercations.

7. Being Late to Set

   • Conor [15:26]: "Connor, you're late for everything."
   • Grace playfully teases Conor about his notorious tardiness, while Ethan discusses his own punctuality.

"In the Green Room" Segment

Grace transitions into "In the Green Room," where the guests rank themselves among Happy Gilmore's five children, adding depth to their fictional portrayals.

Conor [19:02]: "We kind of become like one symbiotic brother."

They humorously portray the dynamics of being part of Happy Gilmore's family, emphasizing their camaraderie and brotherly bond.

Personal Stories and Anecdotes

The episode delves into personal stories, revealing insights into Ethan and Conor's lives:

• Connor's Mischievous Past:

  Connor shares a wild story about swallowing a friend's goldfish as part of a bet, highlighting his penchant for outrageous antics.

  Connor [25:07]: "I swallowed it whole. I didn't chew it."

• Ethan's Experiences with Alcohol:

  Ethan recounts his mishaps with alcohol consumption during auditions and his time in Scotland, illustrating his struggles and humorous failures.

  Ethan [22:20]: "I was really a bad kid."

Shout-Outs and "Disgraceful Receipts"

Grace introduces "Disgraceful Receipts," where Nora, Grace's sister and head of the HR department, presents amusing and cringe-worthy moments of the guests. This segment showcases Grace's comedic prowess and Nora's meticulous research.

Connor [57:41]: "Stu Fry, your chef. Not my show. But he is the chef."

The guests humorously navigate through their personalized "receipts," sharing behind-the-scenes stories and playful banter.

Games and Rapid Fire Challenges

Towards the end, Grace engages Ethan and Conor in rapid-fire games, including "Write in Room," where they attempt to summarize the "Happy Gilmore 2" movie in under 15 seconds. Their earnest yet comedic attempts add to the episode's entertaining vibe.

Connor [40:02]: "So 30 years later, we find Happy Gilmore. He has now lost a lot of stuff in his life..."

Despite initial stumbles, the guests deliver heartfelt and humorous synopses, demonstrating their chemistry and comedic timing.

Conclusion and Co-Host Decision

As the episode wraps up, Grace announces Ethan Cutkosky as the new co-host, citing his engaging and humorous contributions throughout the episode. Conor, while not selected as the permanent co-host, is encouraged to continue participating alongside Grace.

Grace O. Ali [16:12]: "I think Ethan's gonna be my co-host moving forward."

The episode concludes with final shout-outs and a touching acknowledgment of Adam Sandler's positive influence, cementing the episode's blend of humor and heartfelt moments.

Notable Quotes

• Grace O. Ali [02:22]: "Instead of calling people alcoholics, you call them alkies. Yeah, yeah, that's Boston. That's good stuff."

• Conor [15:26]: "Connor, you're late for everything."

• Ethan [22:20]: "I was really a bad kid."

• Connor [25:07]: "I swallowed it whole. I didn't chew it."

• Ethan [41:20]: "I don't need all this anyway."

Final Thoughts

This episode of Disgraceful with Grace O’Malley masterfully blends comedic segments with personal storytelling, offering listeners an engaging and relatable experience. Grace's dynamic interaction with Ethan and Conor unveils the essence of what makes a great co-host, all while celebrating the legacy of Adam Sandler's iconic character, Happy Gilmore.

For those who haven't tuned in, this episode provides a perfect mix of humor, candid moments, and insightful interactions, making it a must-listen for fans of comedy and behind-the-scenes storytelling.