The Herd with Colin Cowherd — Show Me Something

Episode: Sophie Cunningham on Caddying for Caitlin Clark, Country Music Cameos, & West Wilson on BravoCon!

Date: November 13, 2025
Podcast by: iHeartPodcasts and The Volume

Overview

This episode of "Show Me Something" (part of The Herd feed) delivers an energetic blend of sports, pop culture, and personal stories. Co-hosts Wes Wilson and Kevin welcome special guest, WNBA player Sophie Cunningham, to discuss caddying at a celebrity pro-am with Caitlin Clark, her involvement in country music events, and insight from West Wilson about preparations for BravoCon—a major Bravo TV convention. The hosts share candid anecdotes about recent weekends, iconic sporting traditions, the intersection of sports and pop culture, and reflect on notable moments from their own lives. The conversation is lively, humorous, and colloquial, creating a friendly, relatable atmosphere.

Key Discussion Points & Insights

1. Caddying for Caitlin Clark at a Celebrity Pro-Am (30:49–31:47)

• Sophie Cunningham discusses her upcoming role as a celebrity caddy at the GameBridge Pro-Am in Clearwater, Florida.
• She’s alongside stars like NASCAR driver Carson, soccer Hall of Famer Brianna Scurry, and legendary golfer Annika Sörenstam.
• The group includes Caitlin Clark (Iowa women’s basketball superstar) as the cornerstone.
• Sophie admits she’s more focused on energy and fun than the technical side:
  Wes: “Hopefully they're not too serious because I'll get kicked out of the group.” (02:47)
  Kevin: “But you're a caddy, so your job is to bring good vibes.” (30:49)
• Sophie jokes about the casual nature of her caddying: she'll be “carrying a lot of beers” rather than clubs.

2. Country Music Cameos & A Star-Studded Weekend (07:41–08:46)

• Wes shares her experience seeing country artist Riley Green, hanging out with Drake White and Jamie Johnson.
• She ended up on stage taking a shot with the band, sparking friendly ribbing from Kevin about her “black leather jacket with fringe.”
• Family highlights include attending a Mizzou game to support her cousin, leading to a nostalgic conversation about growing up in Missouri.

3. BravoCon Prep and the Fashion Awards (12:15–19:05)

• West details his ambitious mission to stand out at BravoCon, the annual Bravo TV fandom convention in Las Vegas:
  • He’s up for two fashion awards: Best Costume (for a sleepover party 'Scrooged' outfit) and Best Fashion-Forward Moment (the now-viral headscarf and hat look).
    “Mine is the scarf and hat combo, which… I got tagged in pictures of people doing that for six months.” (15:07)
  • Wes encourages everyone to vote and expresses excitement for the event.
    “You'll find out if you win the fashion awards at BravoCon?” – Wes (18:41)
    “Yeah—they have a whole show, like the Emmy's but for Bravicon.” – Kevin (18:48)
  • West is also presenting the “Rookie of the Year” award—an honor he relishes as a former rookie.

4. Panel Life, Conventions, and Fan Frenzy (19:05–22:03)

• West—new to BravoCon—anticipates the chaos, camaraderie, and surprises:
  “From what I can tell, it’s very much like hanging out with people from other shows… it gets a little wild.” (19:24)
• Security measures are surprisingly intense: every personality gets a personal security guard.
• Fans have already messaged him about missed opportunities for photo ops, highlighting the devoted Bravo fanbase.

5. Personal Stories, Small-Town Vibes, and Nostalgia (05:07–07:36, 35:09–38:38)

• Wes shares a heartwarming story about her dad’s daily breakfasts with a cast of Waffle House regulars, including a couple in their 80s getting married:
  “They know his truck, they have his order ready when he walks in.” (05:07)
• Childhood memories, including Walkman CD players and first albums:
  “The first album I ever received… was Outkast, Love Below/Speakerboxx.” – Kevin (35:10)
• The power of having ‘your own music’ as a kid, and making mix CDs for middle school crushes.
• Reminiscing about “Columbia” (the hosts’ Missouri hometown) and their high school relationships.

6. Sports Traditions and Viral Moments (22:03–29:16, 41:05–44:23)

• Chiefs vs. Broncos: The importance of the upcoming NFL game is discussed, with a personal connection as Kevin’s college roommate—Alex Singleton—recently underwent cancer surgery, underscoring the unpredictability of life:
  “Another reminder to men to go check stuff out, because it can happen to anyone, no matter your age and no matter how ‘dude’ you are.” (27:26)
• A lighthearted debate about the etiquette of public proposals at sporting events:
  “If anyone were to propose to me at a sporting event, I would punch them in the nose and leave.” – Wes (41:18)
• Celebrating quirky Texas football traditions, like playoff seeding decided by a literal gas station coin toss (43:00):
  “So what’s more Texas than, like, coin toss, dudes with letter jackets, gas station? It’s so sick.” – Kevin (43:21)

7. Shoutouts to the Military and Pop Culture Milestones (44:23–44:33, 34:59–35:43)

• Saluting the Marine Corps’ 250th birthday and recognizing Veterans Day.
  “Thank you, vets, for everything that you’ve done… We get to live this goofy life because of you.” – Wes (44:23)
• Marking Outkast’s induction into the Rock and Roll Hall of Fame with personal reflections.

Notable Quotes

• On caddying for Caitlin Clark:
  “I also found out I don’t have to carry any bags, so I’m going to be carrying a lot of beers.” – Wes (30:53)

• On BravoCon fashion:
  “If the fits are cool, then I don’t have to, like, give up.” – Kevin (13:11)

• On unexpected viral fame:
  “It is nice when people… give me credit for bringing it [the headscarf and hat combo] back, dude.” – Kevin (15:41)

• Heartfelt on early cancer detection (re: Alex Singleton):
  “It’s just another reminder to men to go check stuff out, because it can happen to anyone, no matter your age and no matter how dude you are.” – Kevin (27:26)

• Waffle House wisdom:
  “They know his truck, they have the order ready right when he walks in. One egg, two pieces of bacon that he feeds the dogs… and iced tea.” – Wes (05:07)

• On public sports proposals:
  “If anyone were to ever propose to me at any sporting event, I would punch them in the nose and I would leave.” – Wes (41:18)

• On tradition:
  “Don’t ever get rid of that, Texas.” – Wes (43:39)

Timestamps: Important Segments

• Caddying for Caitlin Clark and GameBridge Pro-Am: 30:49–31:47
• Country music concert recap: 07:41–08:46
• BravoCon fashion/awards scoop: 12:15–19:05
• Panel schedule and fan interaction at conventions: 19:05–22:03
• Small-town Waffle House rituals: 05:07–07:36
• Walkman nostalgia and first music loves: 35:09–38:38
• Chiefs-Broncos + Friends’ real-life health news: 22:03–29:16
• Sporting event proposals and Friday Night Lights tradition: 41:05–44:23
• Saluting the Marines and Veterans: 44:23–44:33

Tone and Style

• Warm and inviting; conversational, sometimes irreverent.
• Mix of sports banter, genuine friend-to-friend support, and relatable storytelling.
• Playful ribbing, honest opinions, and candid moments.

Summary for New Listeners

If you missed this episode, you’ll feel like you’re catching up with old friends—the laughs, the stories, and even the offbeat debates about etiquette and tradition. Whether it’s the behind-the-scenes of a star-studded golf event, insider prep for BravoCon, or the rituals that keep families and towns connected, the hosts offer stories that blend the world of sports and pop culture with everyday life and humor. Some segments are unexpectedly moving, like updates on a friend’s health scare, while others are lighthearted takes on what’s trending and nostalgic. You’ll come away entertained, informed, and maybe even inspired to check in with old friends—or just have breakfast at Waffle House.