ReLiving Single – "Boss Lady Blues" featuring Shaun Baker (Oct 15, 2025)

Episode Overview

This vibrant episode of ReLiving Single is a heartfelt tribute to Living Single’s iconic “Who’s the Boss?” episode (S1E22). Hosted by the magnetic duo Erika Alexander and Kim Coles—sitcom legends and lifelong friends—the podcast blends hilarious behind-the-scenes anecdotes, character deep dives, and an inspiring conversation with special guest Shaun Baker (who played Russell) about his Living Single debut and creative journey. The central theme: how crisis can spark opportunity, both on-screen and off.

Key Discussion Points & Insights

The Opportunity in Crisis: Setting the Stage

• [00:02, 01:17] The hosts riff on the quote: “Never waste a good crisis,” introducing the episode’s meta-theme. Both recall real-life showbiz moments when sudden shifts (like replacing a headliner or stepping in for an understudy) forced them to rise and shine.
  • Kim: “If I could follow Sinbad, I could follow anybody... It was a crisis, but I rose to the occasion.” ([02:33])
  • Erika: “You gotta stay ready so you ain’t got to get ready.” ([03:20])

Episode Recap: “Who’s the Boss?”

• [04:33] The hosts break down the episode:
  • Khadijah is bedridden with the flu, pushing Sinclair to run the Flavor office—with Regine as an amusingly reluctant “spy.”
  • Overton plays nurse to a hilariously cranky Khadijah back at the brownstone.
  • The writing/directing team gets love: Kim Nastran Dubai & Jeffrey B. Hodes, directed by Terri McCoy (a Black woman, praised as “beloved Terri”).

Delegation, Trust, and Leadership

• [07:08] Khadijah’s struggle to delegate is unpacked:
  • Kim: “Is she just concerned that Sinclair can't do the job or that she thinks, I'm the only one who can do the job?...Delegating really helps you expand even faster and even stronger. Give people the ability to strengthen their own abilities.” ([07:34])
  • Erika: “She knows that she has not trained Sinclair to really do it well. So maybe she does need some eyes on the prize.” ([08:12])
• Sinclair’s professional transformation is celebrated, from her boss-lady look to decisive management:
  • Kim: “You look like a baller.” ([09:35])
  • Erika: “I think it's showing that she [Sinclair] does [have leadership skills].” ([10:10])

The Arrival of Russell: Shaun Baker’s Debut

• [10:37, 13:11] The episode marks Shaun Baker’s first appearance as Russell:
  • Hosts marvel at Baker’s “musicality” and charisma—body and hands fully in the scene, rooted in his Jamaican heritage and theater background.
  • Baker (in character): “Chicken Yard magazine and you in charge? I can’t work like this. I quit.” ([11:26])
  • Discussion on why Russell’s resignation, however over-the-top, made sense: “When you know your worth, you gotta follow your passion and your dreams.” ([14:10])

Shaun Baker Interview Highlights

On Russell’s Walkout and Knowing Your Worth

• Shaun Baker: “Hell, yeah” Russell should have quit. “When you know your worth...you gotta follow your passion and your dreams. For me, it was also to ruffle your feathers a little bit...I knew you [Sinclair] were out of your element.” ([14:10])
• Baker recounts how Russell was originally a one-episode part—his mother mounted a letter-writing campaign to bring him back: “Being on a series is like winning the lottery… it is the gift that keeps on giving.” ([16:36])

On Becoming Russell: Jamaican Roots & Theatrical Energy

• Shaun Baker: “For me, the character was a tribute to my maternal grandparents and to my mom. The music and the culture—codfish and akee and roti and curry goat—that was all there.” ([15:40])

Early Showbiz Origins and Mentorship

• [27:20–31:20] Baker shares memories of growing up surrounded by arts legends (Loretta Devine, Gregory Hines), the influence of his mother’s artistic dreams, and being a “New York showbiz kid” taught to sing, dance, and act at a high level.

Overcoming Rejection and Turning Setbacks Into Opportunity

• [34:55] Profound story from age 12:
  • Cut from The Tap Dance Kid days before the final callback—devastated, but “woodshopped” in the studio, used the setback as fuel, and ultimately booked My One and Only. “Whatever setback you think is a setback, you use it as ammunition to propel you to great things.” ([35:14])

Scene Spotlights & Memorable Moments

Comic Gold: Overton as Nurse, Sinclair as Boss

• The hosts revel in the physical comedy and the dynamic between cranky Khadijah and fussing Overton, the playful antagonism between Kyle and Max (“karma full circle” with bread and jam), and Sinclair’s leadership improvisation.
• Quote: “Pressure makes a diamond. Yes, but you more like a rock." / "I’m like a cubic zirconia.” ([12:22])

Black Women’s Resilience & Representation

• [25:10–26:18] Discussion about viewers seeing themselves onscreen—as Khadijah, Max, Sinclair—propelling fans in real life to “act as if,” and why that matters for representation.

Health, Humor, and Gender Realness

• Kyle claim: “Men have a higher threshold for pain.”
• Erika & Kim’s response: gleeful comedic takedown—“If you had to endure cramps you'd knock yourself out with a blunt object!” ([20:53-21:26])
• Baker: “Men can’t carry a baby for nine months...to give life and carry life—respect to women. Respect. God bless.” ([21:26])

Notable Quotes & Highlights

| Timestamp | Speaker | Quote | |-----------|-------------------|--------------------------------------------------------------------------------| | [02:33] | Kim Coles | “If I could follow Sinbad, I could follow anybody... It was a crisis, but I rose to the occasion.” | | [07:34] | Kim Coles | “Delegating really helps you expand even faster and even stronger. Give people the ability to strengthen their own abilities.” | | [10:55] | Erika Alexander | “He [Shaun Baker] has a musicality to his body...some people act here...he thrusts his body into the room.” | | [14:10] | Shaun Baker | “When you know your worth, you know...you gotta follow your passion and your dreams.” | | [16:36] | Shaun Baker | “Being on a series is like winning the lottery...it is the gift that keeps on giving.” | | [25:43] | Kim Coles | “We have to see ourselves. We have to see our representation. That's why we get so excited—‘That's my cousin, my auntie, that’s me.’” | | [35:14] | Shaun Baker | “Whatever setback you think is a setback, you use it as ammunition to propel you to great things.” | | [43:03] | Erika Alexander | “For Black people, the past is painful, the present precarious, but the future is free. We always see ourselves in the future… Don’t ask us not to see the future.” |

Reflections: Crisis as Opportunity

Erika Alexander & "Concrete Park"

• [40:30–45:23] Erika Alexander recounts fighting industry stereotypes and gatekeeping to create the acclaimed Concrete Park comic book series, turning Hollywood rejection (“Black people don’t like science fiction because they don’t see themselves in the future”) into a new creative pathway. She underscores the importance of DIY and owning one’s narrative.

Kim Coles on Personal Reinvention

• [46:29–49:40] Kim shares her post-Living Single depression, shopping addiction, and a near-breakdown that eventually led her to a new career in standup, public speaking, and coaching. She emphasizes lateral thinking and using “all your gifts” to forge opportunity, unbound by other people’s decisions.

Listener Q&A: True Blue Segment

• [50:10] Listener Amber asks: Who has that famous Living Single women’s faces plate from the set?
  • The hosts confirm: Creator Yvette Lee Bowser has it, celebrating Black art as a cultural marker on TV.

Reverb: Black Excellence

• [37:22–38:42] The hosts riff on “Black Excellence,” joyfully listing family, cookouts, music, hair, and cultural legacy, weaving in humor and pride.

Closing Thoughts

“Boss Lady Blues” is a multi-layered episode brimming with humor, lived wisdom, and genuine vulnerability. Erika, Kim, and Shaun Baker demonstrate how setbacks—on-stage, onscreen, or deeply personal—can catalyze growth and bold reinvention. Whether it’s Sinclair rising to run the office, Russell taking a stand, or the hosts pursuing new creative paths, the message is clear: embrace crisis as a springboard, stay true to yourself, and don’t wait for permission to shine.

For More

• Don’t miss Shaun Baker’s stories about his mom’s campaign, his theater roots, and the “boss-lady” scene breakdowns.
• Listen for advice on creativity, representation, and turning hardship into art.
• Submit your own questions and keep celebrating the legacy of Living Single!

For detailed timestamps, see quotes and discussion breakdown above.