The Bert Show – Full Show PT 2: Tuesday, January 27 [Vault]

Original Broadcast: January 27, 2026
Main Cast: Bert, Kristin, Abby, Cassie, Tommy, and others
Featured Guest: Rihanna

Episode Overview

This episode features two main segments:

1. An engaging and candid interview with superstar Rihanna, delving into topics ranging from lost luggage to fame, media pressure, and her upcoming projects.
2. An extended listener call-in segment focusing on Amy’s relationship dilemma, where the Bert Show cast offers advice and seeks insight from male listeners to help Amy decode her boyfriend’s confusing behavior.

Listeners are treated to the show’s trademark mix of authenticity, humor, and heartfelt advice, set against the backdrop of relatable life and celebrity experiences.

Segment 1: Interview with Rihanna (00:00–21:47)

The Case of the Missing Luggage (00:00–01:22)

• Rihanna calls in instead of making her planned in-studio appearance due to lost luggage en route to Atlanta.
• Quote (Rihanna, 00:37): “Yes, I did. Well, I’m praying to God that it comes in sometime before I leave today for the Bahamas... All my shoes, makeup, toiletries. Every possible thing I could think about.”

Touring & Collaborations with Kanye West (02:01–03:13)

• Rihanna confirms she’s about to go on tour with Kanye West.
• She shares how Kanye personally called her to convince her to join a genre-blending, creative “glow in the dark” themed tour.
• Quote (Rihanna, 02:08): “Kanye, he called me... and luckily, he's not one of those rappers that just sticks to urban radio... He crosses over as well.”

Meteoric Rise & Pressure in the Industry (03:13–05:42)

• Discussing her rapid career ascent since 2005, being named one of US Weekly's top 10 most powerful girls in Hollywood.
• She acknowledges pressure to continually outdo herself.
• Quote (Rihanna, 04:13): “Every time I go a little further in my career, the pressure gets more intense... You don’t ever want to take a step backward.”
• She admits to being a workaholic, even missing work while on vacation.

Grammy Nominations & Performing Under Pressure (05:46–07:41)

• Rihanna is celebrated for her six Grammy nods, especially for “Umbrella” and “Good Girl Gone Bad.”
• She’ll perform with legendary 80s band The Time, blending influences and eras.
• On performing for industry icons:
  • Quote (Rihanna, 06:45): “Hell yeah. It is so nerve wracking. I mean, you perform in front of thousands of people every night, but the minute the crowd is people that do what you do or have done what you do, it puts so much pressure on you.”

Addressing Media Rumors & Relationship with Beyoncé (07:45–09:18)

• Rihanna dismisses rumors of tension with Beyoncé as “ignorant.”
• Both have learned to weather negative press, stressing mutual respect but not close friendship.
• Quote (Rihanna, 07:55): “I don’t really address it because it’s kind of ignorant to me… but in the back of their head, they know that there’s nothing going on between me and Jay Z.”

Navigating Media Scrutiny (09:19–11:30)

• Rihanna describes the ups and downs of online criticism and tabloid rumors, particularly about her dating life.
• No rumors have accidentally been true—most come from chance meetings or friendships, not actual relationships.

Style Influence & The Bob to Pixie Cut (13:19–14:44)

• Rihanna discusses her iconic bob hairstyle, its global influence, and her recent shift to a shorter “pixie” cut for 2008.
• She works collaboratively with her hairstylist for her unique looks.

Homecoming & Barbados Culture (14:49–18:34)

• Reflects on mixed perceptions in her home country: immense pride from some, jealousy from others.
• Shares nostalgia for Barbados, especially clubbing as a teen, and clarifies misconceptions Americans have about the island’s modernity.
• Quote (Rihanna, 17:45): “I’ve definitely been asked if I have inside bathrooms before…”

“Body by Milk” Campaign & Image (18:34–21:24)

• Rihanna explains her advocacy for youth health in the “Body by Milk” campaign.
• She addresses the increasing “sexiness” in her public image, noting it's driven by personal expression and artistic themes, not an intention to be provocative.

Future Plans (21:02–21:24)

• Hints at new music, movies, and fashion projects—expanding her brand beyond just music.

Segment 2: Amy’s Relationship Dilemma (21:47–39:02)

Amy's Relationship Story (22:19–24:46)

• Amy calls in seeking advice about her on-again, off-again boyfriend who claims he “loves” her but isn’t “in love” with her, often pulling her back after breakups.

The Panel & Callers Weigh In (24:46–36:17)

• Bert and the cast ask male listeners for insight, seeking to “crack the code.”
• Consensus among male callers: her boyfriend likes having Amy as a backup, is afraid of being alone, and may not have another woman but still isn’t truly committed.
• Honest feedback urges Amy to move on for her own emotional health.
• Quote (Bert, 32:28): “Zero tolerance for disrespect. Zero. And he’s done it to you time and time again... Now, if you keep going back... now it's your fault if you get hurt.”

Tough Love and Advice (36:17–38:54)

• The cast provides tough but loving advice—telling Amy that clinging to hope is just prolonging pain.
• Emphasis on self-worth, moving on, and not accepting less than she deserves.
• Quote (Female cast, channeling Jen Hobby, 33:25): “There will be a guy out there... who will definitively tell you, ‘I love you, I’m in love with you, I want to be with you’... and he's not going to be the one to do it.”

Final Thoughts – Breaking the Cycle (38:54–End)

• The group reflects on the importance of direct, honest communication in relationships and the necessity of walking away when respect is lost.
• Amy acknowledges her need to be strong and not be drawn back into the cycle.

Notable Quotes & Memorable Moments

• On Work Ethic:
  “If not by choice, sometimes by force. But I am always... always working. When I’m not working, I’m thinking about working and missing work.” – Rihanna (04:52)

• On Media Rumors:
  “Sometimes when I read, like, those gossip sites and I read the comments, oh my gosh, I want to kill myself by the time I finish reading... You cannot ever please everybody.” – Rihanna (09:36, 10:17)

• On Commitment:
  “He told you he loves you, but he's not in love with you. And it means exactly what it means. He loves you like a mom. He loves you like a friend.” – Intern Carl to Amy (30:33)

• Encouragement:
  “Start building yourself some self-esteem points right now.” – Bert to Amy (38:21)

Timestamps for Key Segments

• Rihanna’s Luggage Drama: 00:00–01:22
• Tour with Kanye Details: 02:01–03:13
• US Weekly “Powerful Girls” Ranking: 03:13–05:42
• Grammy Nominations & The Time Performance: 05:46–07:41
• Beyoncé & Media Rumors: 07:45–09:18
• Online Criticism & Dating Rumors: 09:19–11:30
• New Hairstyles & Influences: 13:19–14:44
• Barbados Reflections: 14:49–18:34
• “Body by Milk” & Image: 18:34–21:24
• Amy’s Relationship Story: 22:19–39:02

Summary

This episode blends celebrity candor and personal struggle, illustrating The Bert Show's ability to make the superstar accessible and offer heartfelt, actionable advice to real listeners. Rihanna shines with honesty about the pressures and joys of fame while holding true to her individuality and roots. The second half’s deep dive into relationship confusion is both entertaining and helpful, with the cast and listeners rallying around Amy to deliver the tough truths that so many need to hear — all with compassion and characteristic humor.