"Building a Legacy with Kym Whitley"

Legacy Talk with Lena Waithe
Date: September 30, 2025

Episode Overview

In this heartfelt and hilarious episode, Lena Waithe sits down with renowned comedian, actress, and storyteller Kym Whitley. The pair dive deep into Kym’s journey through Hollywood—from her unforgettable comic performances on legendary sitcoms like "Martin" and "The Wayans Bros." to her scene-stealing movie roles, powerful voiceover work, and her evolution into an award-winning, resilient artist and single mother. The conversation covers themes such as navigating fear, finding one’s comedic voice, the importance of mentorship and community, and the legacy of joy and authenticity. Lena offers a loving, affirming space to reflect on the struggles and triumphs of Black women in entertainment, while Kym brings her signature candor, wisdom, and wit.

Key Discussion Points & Insights

1. Kym’s Entry into Comedy and Early TV Roles

• Lena and Kym reminisce about their first encounters and how Lena always admired Kym’s ability to step up and make things happen once she said she would. ([00:54]–[01:26])
• First major TV role: Kym appeared on "The Sinbad Show" in a church-centered episode with Nancy Wilson and a young Ray J. Kym discusses her nerves entering multicam sitcoms, struggling to balance being "big" and funny without going over the top. ([02:10]–[05:15])

Notable Quote:
"Multicam is a different kind of energy than, say, single cam or movies ... I always tried to find what was that fine line between being funny, being big, and not getting fired."
— Kym Whitley ([03:12])

• She candidly shares her discomfort with love scenes and being typecast:
  "I've never been good in a love scene. I was never comfortable with it ... even though I've always been a sexual character on TV." ([04:50])

2. Landing Guest Roles on "Martin" & The Power of Community

• Kym’s audition for "Martin" was orchestrated through personal connections—no agents at the time. Producer Bentley Evans literally pulled her out of her first audition to urge her to do better, reminding her of her strength. The second try, she booked it. ([07:14]–[09:05])

Notable Quote:
"Bentley stops and says, ‘Hold up.’ He takes me out of the audition into the hallway and cusses me out ... ‘I know you're funnier than that ... give it to them.’ So that became me being the robber and had a ball with it."
— Kym Whitley ([08:57])

• Reflections on the lack of mentorship and wishing she’d asked icons like Jennifer Lewis for guidance earlier:
  "One of my biggest regrets is that I did not grab onto Jennifer Lewis … I should have asked ... but when you come into this business, for some reason young, you don’t open your mouth…” ([13:00])

3. Vulnerability, Fear, and Asking for Help

• Kym opens up about reluctance to reach out for support:
  “I want our friendship to be intact. I don’t ever want to be the person that's like, ‘Hey, can you ... ?’ ... I feel like I’m saving for the ask.” ([14:52])
• Lena encourages her to see asking for help as strength, not a burden.

4. The Art of Going After Roles: "The Wayans Bros." and "Next Friday"

• Details how she doggedly pursued the role of obsessive fan Phyllis in "The Wayans Bros.," going so far as to use prosthetic teeth and purposely unkempt hair for the audition. Persistence, commitment, and comedic transformation paid off. ([18:16]–[23:10])

Notable Quote:
"When you want something and you feel like, ‘I can really do this,’ you show them instead of telling and begging."
— Kym Whitley ([21:27])

• “Next Friday”: Kym discusses auditioning for Suga, crafting the character with props, wardrobe choices, and leaning into her comedic, sexy side despite discomfort. ([33:00]–[38:12])

Memorable Moment:
“I took out this bottle of liquor ... Cognac ... All I remember was Ice Cube hitting the floor. Bam. And as a comic, you’re like—got him!” ([33:12])

5. Navigating Sexualized Roles & Self-Image

• Explores her recurring typecast as a comic “sexpot,” examining the conflict between audience expectations and her tomboy upbringing.
  "That was the first time I was like, you sexy. You alright ... That’s what showed me I could be alright ..." ([42:04])

• Touches on the protection mechanisms she developed growing up tall among boys, her struggle to access her feminine side, and the tension this created in both professional and personal life. ([27:18])

6. Legend-Laden Films: "Nutty Professor 2" & Working With the Greats

• Reveals that many of her roles in big films like "The Nutty Professor 2" came from being “in the mix”—hanging out at offices, helping people—and then being called for a last-minute cameo.
  "The residuals from that small scene were bigger than what I was making on a TV show." ([48:20])

• Talks nerves and validation:
  "Even when people call me and they're like, Kim ... what do you see in me that I don't see in myself?" ([55:15])

7. Voiceover: The Boondocks and Beyond

• Shares imposter syndrome and technical challenges faced in voiceover, especially for "The Boondocks," despite recurring casting. ([57:18])
• Credits her comedic timing and delivery for her success, even when unsure of her “voice acting” skills. Encourages gratitude through thank-you gifts and mutual support in the industry.

8. Improvisational Genius: "Curb Your Enthusiasm"

• Auditioned sans knowledge of Larry David’s cultural status or "Seinfeld," just ready to improvise as a “prostitute”—with help from Katt Williams and friends for authentic lines.
  "They called me and said, you raised the bar so high that ... we couldn't unsee you." ([66:38])

• Details the spontaneous and communal nature of the set, the freedom on "Curb," and the iconic Dodgers game filming, plus the famous real-life exoneration that resulted from the episode.
  "I would have never thought playing a prostitute with Larry David would become so iconic." ([77:28])

Memorable Moment:
"First time you go [to a Dodgers game], you go with Larry David ... as a prostitute." ([76:31])

9. Recent & Personal Projects: "Master of None," "Twenties," and "Kim" Audible Series

• Lena recounts handpicking Kym for "Master of None: Thanksgiving," appreciating her maternal warmth and authenticity in the role.
  "You are like an aunt. You always say I'm your niece and you're Aunt Kim … our genuine love that we have for each other. We didn’t have that much acting to do." — Lena Waithe ([85:41])

• Kym talks about the gravity and challenge of embodying Hattie’s mother in "Twenties," and the importance of keeping her comedic style grounded for dramatic scenes. Acting coach and connecting deeply with cast helped her succeed. ([94:35])

Notable Quote:
"It is 80, 90% personality and kindness. It’s 10% talent ... because I bring a light. I love people." ([103:30])

• Reflects on the award-winning "Kim" audible series, collaborating with Lena to dramatize her real story of single motherhood, recalling both laughter and vulnerability in retelling real moments. ([106:03])

10. Legacy and the Comedic Actress

• Kym defines a phenomenal comedic actress as one who embodies freedom, mastery of timing, joy, and genuine emotion.
  "You love that, but you wanna hang out with that person ... You cannot be a great comedic actress without knowing timing, when to hold, when to fold, and when to run." ([113:46])

• Lena pays tribute to Kym’s unique ability to bring truth, humor, and warmth to every role, making the audience feel seen and included in the joke, never judged. Kym feels the impact of having her work genuinely celebrated:
  "You don't get interviews where you talk about your work. So I thank you for doing the research and digging deep into who I am." ([116:50])

Notable Quotes & Memorable Moments

• "When you want something and you feel like, 'I can really do this,' you show them instead of telling and begging." — Kym Whitley ([21:27])
• "For me, a lot of it has been fear ... I do it anyway. I do it in spite of." ([17:31])
• “People see something in me that I don’t see in myself.” ([62:29])
• "You represent all of us ... that fear that you talk about, that wanting to do well for the people that are rooting for you." — Lena Waithe ([115:54])
• "It's 80, 90% personality and kindness … It’s 10% talent … I bring a light. I love people." — Kym Whitley ([103:30])
• "[Voice acting] is the hardest thing for me. Because my voice, I feel, is pretty monotone ... I have not mastered that." ([59:38])
• "I always had that on my door—that I stayed youthful. 'You've just begun.'" ([55:15])

Key Timestamps for Important Segments

• Early TV & the Sinbad Show: [02:10] – [05:15]
• Auditioning & Breakthrough on Martin: [07:14] – [10:13]
• Mentorship & Regret: [12:48] – [14:39]
• Wayans Bros. Audition: [18:16] – [23:10]
• "Next Friday" & Suga: [33:00] – [38:12]
• Typecasting & Self-Image: [27:18] – [30:53]
• "Nutty Professor 2" Featuring Eddie Murphy: [46:19] – [52:18]
• Voiceover Work (Boondocks): [57:15] – [63:31]
• "Curb Your Enthusiasm": [65:50] – [78:03]
• Master of None & Thanksgiving: [78:16] – [88:35]
• On Set with David Arnold, Standup, and "That Girl Lay Lay": [89:07] – [94:05]
• Portraying Hattie's Mom on "Twenties": [94:35] – [103:30]
• "Kim" Audible Series & Voice Acting: [104:51] – [112:52]
• Legacy, Being a Pillar, and Defining a Comedic Actress: [113:37] – [116:09]

Final Reflections

This episode stands as both a masterclass in comedy and a testament to the power of persistence, friendship, vulnerability, and the Black storytelling legacy. Kym Whitley's career—navigating fear, breaking barriers, and showing up with her inimitable warmth—reminds listeners that legacy is not just about the roles played, but the lives touched and the fire you bring into the room, onscreen and off.