IMO with Michelle Obama and Craig Robinson

Episode: “Share the Shine” with Kenan Thompson

Date: October 29, 2025
Guest: Kenan Thompson
Hosts: Michelle Obama & Craig Robinson
Producer: Higher Ground

Episode Overview

This lively episode of IMO centers on the enduring magic and pressures of fame, family, and creative work in show business. Michelle Obama and her brother Craig Robinson welcome legendary comic and actor Kenan Thompson for a candid, humorous, and heartfelt conversation. They share parenting stories, discuss Kenan’s remarkable longevity on SNL, and tackle a listener question about children wanting to be famous. Throughout, the guests “share the shine,” exploring the importance of community, support, and perspective in both career and parenting.

Key Discussion Points & Insights

1. Kenan’s Childhood and Path to Comedy

• Kenan reflects on growing up in Atlanta, his tight-knit family, and his early foray into acting and commercials (13:42).
  • “My parents are from small town Virginia... all my cousins, extended family from around that area and spent a lot of summers growing up there. So I have a perspective of, you know, what it's like to maybe not have grown up with a lot of opportunity.” — Kenan Thompson (13:29)
• His child acting career began at age 5 but didn’t become “real work” until his mid-teens.
• His first “real” paycheck ($800 at age 11) inspired him to take performing seriously (13:52).

2. On Parenting and Sibling Bonds

• The hosts and Kenan discuss raising children, fostering sibling closeness, and preparing kids for adulthood (10:05–12:28).
  • Kenan emphasizes teaching his daughters the value of their sibling relationship:
    • “This sibling bond you have is very strong. It’s probably the strongest on the planet. But if you don’t use it the correct way… you waste the young years…” — Kenan (11:30)
• They share stories of giving their children more independence while maintaining core values.

3. Kenan’s Career Trajectory & Humility

• Kenan recalls humble beginnings — headshots at Sears with borrowed sweaters (15:07), missing out on parts, and early big breaks.
• The journey to Nickelodeon and Good Burger marked Kenan’s iconic entrance into mainstream success (21:31).
• Both Craig and Kenan underscore the crucial role of supportive parents. Kenan credits his mother for “pushing” and guiding him (22:15).

4. Fame, Nerves, and Stage Fright

• Despite decades in the spotlight, Kenan admits he still feels nerves before every SNL show and dislikes doing stand-up due to anxiety (26:01).
  • “If I have a gig, that's all I'm thinking of the whole day. You can't sleep days out. I'm just... I can't not focus on that.” — Kenan (26:02)
• Craig confesses he’d be terrified to do SNL, emphasizing how daunting live comedy can be (26:34).
• Kenan explains the importance of preparation and writing for oneself on SNL to build visibility and confidence (28:01).

5. Mentorship and SNL as a Temple

• Tracy Morgan was a guiding force for Kenan as a new cast member, providing “golden nuggets” like “don’t peak at dress” (32:04).
• Kenan now strives to be that calm, supportive presence for newcomers, focusing on ensemble spirit:
  • “Let somebody else have the shine and I will help that shine be as bright as possible.” (34:20)

6. Navigating Fame and Privacy

• The group discusses the loss of anonymity and the impact of fame not just on themselves but on family (42:51).
  • “It’s terrible to be the cause of stress, you know. So that bothers me, especially in public... if you run into me on those days, I'm sorry, you know what I'm saying? But it happens.” — Kenan (45:06)
• Kenan prefers his children not participate in public moments that interrupt family time.

7. Sustaining a Healthy Career

• Kenan credits a strong family foundation and lived experience for navigating Hollywood’s pitfalls — “trouble gonna find you if you go looking for it,” but he’s fine staying out of the chaos (46:20).
• Balance is now more important than “turning up”:
  • “Netflix and chill” over partying; understanding responsibilities comes with age (47:06).

8. Listener Question: Kids & the Pursuit of Fame

• Listener Sandy from New Jersey seeks guidance about her daughter wanting to be a social media influencer (57:56).
• Kenan, Michelle, and Craig warn against seeking “fame for fame’s sake.”
  • “If you’re attached to being famous, then that’s the most heartbreaking thing… you’re gonna get aged out.” — Kenan (58:41)
• Focus should be on passion and personal growth:
  • “Keep your child focused on the passion. And if there’s a real passion there, encourage it.” — Craig (64:41)
• They underscore family is key: “It can't just be for them… parents that are focused, not pushing you past your boundaries necessarily, but encouraging.” — Kenan (66:04–66:53)

9. Real-life Parenting: Kenan’s Daughters Join the Show

• Kenan’s daughters, Georgia and Gianna, make a surprise cameo (68:32–70:50), enhancing the “share the shine” theme.
  • Craig offers advice: “As the big sister, sometimes she may get on your nerves... But in the end, you guys really do just have each other.”

10. Pep Talk for Burnout

• The episode ends with advice for a listener (Nora) struggling with burnout (73:39):
  • Michelle prescribes exercise, while Craig advises scheduling stress-reducing activities first (74:29).

Notable Quotes & Moments (with Timestamps)

• Kenan’s “fake it till you make it” story:
  • “I remember when I auditioned for the Mighty Ducks… they asked if I could skate and I was like, yeah, I can roller skate. Couldn't roller skate at all. But… they say, put special skills at the bottom of the resume… I used to fall two feet up roller skating.” — Kenan (00:00, 23:41)
• On SNL nerves:
  • “I still get nervous for every show… That’s why I don’t do stand-up. Cause it stresses me out.” — Kenan (26:01)
• On sharing the shine:
  • “Let somebody else have the shine and I will help that shine be as bright as possible.” — Kenan (34:20)
• On fame & privacy:
  • “It’s invasive. And it’s tougher for me when it’s tough on other people… It’s terrible to be the cause of stress.” — Kenan (42:51)
• Advice to parents of aspiring influencers:
  • “Focus on… what’s the passion behind all that pursuit? The passion is something that’s good for the world, I can get behind that.” — Kenan (59:41)
• On family as the anchor:
  • “[The] common denominator of the ones that have been able to navigate it is family… Not necessarily pushing you past your boundaries necessarily, but encouraging.” — Kenan (66:04–66:53)
• Heartwarming closing with Kenan’s kids:
  • “One of the things your dad told us that he wants to make sure you guys always know is that you guys have each other forever… But in the end, you guys really do just have each other.” — Craig (69:45)
• Pep talk for burnout:
  • “Put yourself on your calendar first. Thanks again, Nora, for your great question.” — Craig (74:29)

Timestamps for Major Segments

• Kenan’s Early Years & Family (13:42–15:17)
• First Breaks & Nickelodeon (21:24–23:14)
• SNL, Confidence, and Nerves (26:01–27:48)
• Mentorship & SNL Culture (32:04–33:52)
• The Realities of Fame (42:51–45:49)
• Listener Question: Kids Who Want to Be Influencers (57:43–68:32)
• Kenan’s Kids Appear (68:32–70:57)
• Pep Talk for Burnout (73:39–75:33)

Episode Tone

Friendly, honest, and frequently hilarious—this episode blends childhood nostalgia, behind-the-scenes industry wisdom, and deeply authentic parenting insight. Kenan’s warmth, humility, and comedic energy mesh perfectly with Michelle and Craig’s playful sibling rapport, delivering an episode that’s as insightful as it is entertaining.