The Toast – “Slay of the Day: Monday, September 29th, 2025”
Hosts: Jackie & Claudia Oshry
Date: September 29, 2025
Episode Overview
This lively Monday episode delivers a blend of sports recap (Ryder Cup, Super Bowl halftime news), celebrity pop culture (Selena Gomez’s wedding, Madelyn Cline’s royal romance), cultural controversies (Riyadh Comedy Festival debate), and signature sisterly banter. Jackie and Claudia reflect on their own lives (motherhood, kitchen gadget drama), and keep listeners entertained with opinions, advice, and the “Fast 5” headlines “you need to know.” The tone is warm, candid, and sprinkled with humor.
Main Segments & Key Discussion Points
1. Latina & Sports-Themed Monday Warm-Up (00:05–03:16)
- Claudia greets listeners and notes a “Latina inspired show” with lots of sports news.
- Jackson talks about attending the Ryder Cup, jokes about the price of merch, and shares excitement about gifting Claudia a women’s Ryder Cup hat.
- Memorable Quote (01:22, Jackson): “That's like the official hat of the weekend.”
2. Ryder Cup Recap — Logistics, Fans, & Motherhood Realness (03:16–11:40)
- Jackson details the impressive organization and facilities at the NY Ryder Cup venue, emphasizing how “stroller-friendly” and inclusive the event was for families.
- She describes the challenge of bringing baby Ruby and navigating event logistics as a mom (“the push and pull with motherhood”).
- They exchange perspectives on the media narrative of “rowdy” American fans and contrast it with Jackson’s positive, supportive, “civilized” on-the-ground experience.
- Notable Moment (06:28, Claudia): “He’s not going to nap at the Ryder Cup. He’s witnessing history.”
- Memorable Quote (10:27, Jackson): “When we were leaving...so many people were like, what do you need?... I just remember being, like, stunned at how, like, nice everyone was being.”
3. Super Bowl Halftime Show Reveal: Bad Bunny Controversy (12:23–26:54)
- Claudia and Jackson react live to the news that Bad Bunny will headline the 2026 Super Bowl halftime show.
- They reflect disappointment that a pop “girly” (Taylor, Miley, Adele) wasn’t chosen, particularly after several male headliners.
- They discuss the NFL’s push for global appeal, pointing out Bad Bunny’s worldwide dominance vs. the league’s effort to reach more female fans.
- Memorable Quote (24:01, Jackson): "I'm happy for my community. But, like, is this who I would have chosen? No. No."
- Noted: Bad Bunny doesn’t get paid for the performance (standard for Super Bowl) and had recently skipped US tour dates for political reasons.
- They recite Bad Bunny’s statement on representing his culture:
Quote (26:38): “...This is for my people, my culture and our history.”
4. The Riyadh Comedy Festival Debate (26:55–35:05)
- In-depth discussion on controversy over top comedians (Kevin Hart, Dave Chappelle, Bill Burr, Whitney Cummings, etc.) performing at a Saudi-sponsored event, weighing the high payouts against Saudi Arabia’s human rights history.
- They discuss the “gray areas” of artists’ responsibility, the surprise at political comedians accepting, and how social media exploded with criticism.
- Pete Davidson and Tim Dillon’s involvement (and Tim’s subsequent removal for crossing the line with a slavery joke) are recounted.
- Notable Quote (31:44, Jackson): “I can be bought. I’m just, like, not really down to go to Saudi Arabia.”
- They contextualize the debate in light of similar sports crossover: “it all comes back to golf.”
5. Ryder Cup Breakdown & Fan Drama (35:05–45:50)
- Recap of Ryder Cup results: US team loses to Europe, despite a late comeback.
- Jackie and Claudia voice confusion at golf scoring, critique US player performance, and analyze Europe’s stronger team camaraderie.
- They break down the fan controversy surrounding Rory McIlroy and specifics of heckling that crossed the line (personal insults to Rory and wife).
- Both reflect on emotions of players, the intricacies of international team tournaments, and Ryder Cup traditions.
- Memorable Quote (37:27, Jackson): "...they wanted it so bad. They had the heart. They didn’t have the skill."
- Discussion of PGA-LIV Golf merger and its ethical implications.
6. Banter: Kitchen Gadgets & Marital Negotiations (14:05–18:23)
- Claudia and Ben’s “food processor fight” offers a humorous look at spousal compromises and small-space living.
- Claudia laments influencers (Ina Garten) who inspire Ben to clutter the kitchen with gadgets they’ll never use.
- Memorable Quote (16:48, Jackson): “Just because fucking that bitch Ina cooks with it, like, I’m seriously so fucking done with Ina.”
7. Pop Culture Headlines: The “Fast 5” (46:12–65:37)
A. Selena Gomez & Benny Blanco’s Wedding (45:58–47:31)
- Surprise: Selena Gomez and Benny Blanco married in Santa Barbara, private but with some artsy social media shares.
- Taylor Swift rumored to have attended; speculation about her incognito status due to stalker concerns and album promo.
B. Miranda Priestley Meets Anna Wintour: “Devil Wears Prada 2” Meta Moment (56:31–60:09)
- Meryl Streep (as Miranda Priestley) meets Anna Wintour at Milan Fashion Week for filming—life imitates art.
- Discussion on Anna’s real-life feelings about her portrayal; the practice and impact of filming at “real” fashion events.
- They reminisce about Met Gala invitations and speculate on past Hollywood/pop-fashion intersections.
C. Madelyn Cline & Prince Constantine Alexios: Royal Romance (61:09–65:37)
- Outer Banks star Madelyn Cline was spotted with Prince Constantine Alexios of Greece and Denmark—a true “Slay of the Day.”
- Commentary on how “celebrity meets royalty” is a major social upgrade and a rare, chic achievement.
- Quote (64:37, Claudia): “They could keep, like, circling the dream with Austin Butler...you will never be a prince. No matter how many accents you fake.”
Notable Quotes & Memorable Moments
-
On Ryder Cup optimal logistics:
“I could not get over the organization of it all…When you were getting online to go check out. Before you did that, there was like a little station where they removed your hangers. Like, just things like that nobody would think of.”
— Jackson, 03:44 -
On navigating motherhood at big events:
“Now I feel like this is sort of like the push and pull with motherhood. Like, don’t want to go anywhere without my baby. Going with my baby is no longer fun.”
— Jackson, 06:33 -
On Bad Bunny’s statement:
“What I'm feeling goes beyond myself. It's for those who came before me and ran countless yards so I could come in and score a touchdown. This is for my people, my culture and our history.”
— Recited by Claudia, 26:38 -
On comedy, politics, and Saudi Arabia controversy:
“I think a lot of like the consumers of comedy are sort of like intellectual people who like, wouldn't let this — expect better from their faves.”
— Jackson, 34:07 -
On Madelyn Cline dating a Prince:
“When you’ve really kind of scorched the young Hollywood eligible bachelor list, like, the only place you go naturally next is royalty overseas.”
— Jackson, 61:48
Timestamps for Key Segments
| Time | Segment | |-----------|------------------------------------------------------------------------| | 00:05–03:16 | Intro, merch, Ryder Cup logistics | | 03:16–11:40 | Ryder Cup experience, baby Ruby, event organization, motherhood push & pull, fan behavior | | 12:23–14:43 | Super Bowl halftime show reveal, NFL’s global strategy, disappointment over lack of “girlies” | | 26:55–35:05 | Riyadh Comedy Festival controversy, free speech, performer pay, comedy ethics | | 35:05–45:50 | Ryder Cup breakdown, scoring, US loss, team dynamics, fan controversies | | 14:05–18:23 | Claudia vs. Ben: The food processor marital battle | | 45:58–47:31 | Selena Gomez & Benny Blanco’s wedding, Taylor Swift speculation | | 56:31–60:09 | Miranda Priestley & Anna Wintour at Milan Fashion Week, fashion meta moment | | 61:09–65:37 | Madelyn Cline–Prince Constantine: Royal romance and “Slay of the Day”|
Signature Bantz: Host Highlights
- Claudia brings witty skepticism and the “fast five” energy, keeping the show on-pulse with pop culture and sports.
- Jackie (Jackson Claude) dives into relatable anecdotes, organizational appreciation, and “on the ground” perspectives, especially about motherhood and event experience.
Episode Takeaways
- Sports news blends with relatable life updates and critical takes on fan/athlete culture.
- Pop culture news is analyzed through the lens of female fandom, with an emphasis on representation and new “it girl” moments.
- Candid reflections on motherhood, marriage, and how cultural trends intersect with personal life.
- New recurring joke/segment seeded: “Slay of the Day”.
Best for: Listeners wanting a crash course on the week’s biggest sports and celebrity headlines, seen through the sharp, humorous, and honest lens of Jackie and Claudia Oshry. Perfect for catching up on the conversations you’ll be having with friends, significant others, and group chats all week.
End Quote:
“Slay of the day. Let’s see if it catches on.” — Claudia, 65:16