The BobbyCast: Milo Ventimiglia on His First Big Yes, Gilmore Girls, and This Is Us

Date: February 24, 2026
Host: Bobby Bones | Guest: Milo Ventimiglia
Main Theme:
A candid, wide-ranging conversation with acclaimed actor Milo Ventimiglia, exploring his early career “yes” moments, acting approach, industry stories, lessons learned from mentor figures, and his starring role in the new movie I Can Only Imagine 2. The interview delves into the evolution of Milo's career, craft, and personal growth, touching on fame, life lessons from loss and gratitude, and authentic storytelling.

Episode Overview

Bobby Bones sits down with Milo Ventimiglia in Nashville to discuss the pivotal moments and unexpected turns in his career—from his first TV role to breakout parts in Gilmore Girls, Heroes, and This Is Us. They dive into Milo's preparation for roles, his experience auditioning, working with icons, and how personal experiences and adversity have shaped his acting. They also discuss his latest project, I Can Only Imagine 2, and the challenge of portraying real-life figures. The episode is rich with practical advice, life reflections, memorable stories, and warm humor.

Key Discussion Points & Insights

1. The Three Most Asked Questions (01:41 – 08:04)

• On the Ending of This Is Us (01:46 – 04:04)

  • Milo shares that the series' emotional climax was planned out as early as season three:
    • “Dan Fogelman...knew exactly what he wanted to do with the end ... at the beginning of season three.” (01:56)
    • He praises the shift to focus on the mother’s journey: “A beautiful love letter to the strength of women.” (02:38)

• First Big Role on Fresh Prince of Bel Air (04:07 – 06:37)

  • “Party guest number two” at age 18 (“I was going to UCLA... got a phone call...got a yes to be on Fresh Prince of Bel Air.” 04:21)
  • Will Smith’s kindness and professionalism had a lasting impact on Milo’s own set etiquette:

    “Will knew everybody’s names, embraced everybody... I was a kid who had one line. He walked up to me, stopped to talk to me five or six minutes... set me in a direction to make sure every set I was on, hey, be like Will Smith.” (05:16)

• Correct Pronunciation of ‘Ventimiglia’ (06:40 – 08:04)

  • “Ventimiglia. Yeah, G is silent... never offended by it. I realize it’s a difficult last name.” (06:52)
  • Anecdotes about regional Italian pronunciations and having a unique first name.

2. Perspectives on Rural Upbringings and Life Experiences (08:04 – 13:18)

• Bobby shares stories about rural Arkansas—trout trucks, having guns in trucks, and fishing—while Milo jokes about his Orange County, CA upbringing.
• Both discuss challenges with motion sickness on boats and airplanes:
  • Milo gives a practical tip: “Pressure points on the inside of your wrist... should help you to bridge the gap when you’re having motion sickness.” (11:09)

3. Experiencing Fighter Jet Flights (13:18 – 19:30)

• Both recount civilian flights in military jets (Blue Angels, F16s); talk about G-forces, “chirping” breathing technique, and the physical toll:
  • “I hit eight and a half Gs before I finally succumbed and passed out and absolutely vomited.” – Milo (16:35)
  • Both get honest about incapacitating nausea afterward.

4. Military, Adrenaline, and Life Experiences (19:30 – 23:29)

• Milo describes his work supporting military families and experiences like skydiving with Army Special Forces:
  • “Actors just kind of get to do cool things ... do a lot of work with gold star families...that was just one of those things, got invited [to Luke Air Force Base]... spend time with the Air Force Reserves.” (18:38–19:30)
  • On adrenaline: “Not so much out of boredom, but like curiosity...not really, not like ... now being a father.” (22:07)

5. On Curiosity & Lifelong Learning (23:29 – 24:31)

• Milo’s approach to new skills: “Let me do something different with my brain. So I went back to school, started with three languages... stuck with Japanese for two years.” (23:40)
• Emphasizes staying mentally active for the joy of learning, not boredom.

6. Major Career “Yes” Moments & Career Trajectory (24:31 – 27:07)

• Milo recounts moving from day jobs to TV work:
  • “I was selling snowboards...waiting tables... then Gilmore [Girls] kind of put me on the map...Heroes put me above the map...This Is Us hit a whole other stratosphere.” (24:53–25:39)
• On the shift from industry recognition to global fame and learning from prolific co-stars.

7. This Is Us as a Cultural Touchstone & Its Impact (26:43 – 32:25)

• Milo and Bobby discuss the show’s cultural resonance and rare broad appeal:

  • “It was so big, so fast...it made me feel something...as artists, that emotional vulnerability, that emotional connection, that’s what we do...” (27:09)
  • “We on the inside were feeling it and then everybody on the outside is feeling it.” (28:24)
  • “...able to take a point of view and just show it from a slightly different angle...you’re able to understand something and apply it to your own life.” (28:48)

• Audition Process for This Is Us:

  • Initial perception he might be better for Kevin, but was asked to read for Jack. The connection in the room was immediate and led to a quick offer:

    “By the time I get back to my motorcycle, I get a call from my reps, like, ‘Hey, they want you.’” (30:59)

  • Chemistry reads with Mandy Moore and anecdotes about casting.

8. Fame in a Fractional Era (32:25 – 33:34)

• “That was one of the last things where everybody...knew it. It didn’t matter where you were from.” (32:50)
• Discussion on how fame is now niche and This Is Us crossed those boundaries.

9. Playing Real People vs. Fictional Characters (33:34 – 39:54)

• Playing Tim Timmons in I Can Only Imagine 2:

  • In-depth on dialect work, accent coaching, learning music and “inhabiting” a living person:

    “My job is to give an honest existence, not performance, honest existence, representing this real human being...I had a separate dialect coach...the second I was able to plug that [overbite] into my Tim talk, I could capture Tim.” (35:06)

• Challenge of learning guitar, singing, and coordinated performance:

  • “Not only did Milo have to learn how to play four songs...sing, I played kick drum with a heel, tambourine, harmonium all at the same time...they threw the harmonium...a week before we filmed.” (39:01)
  • Audio blending: “They took my voice and Tim’s voice and just put them together...as this kind of combo, hybrid Hollywood movie version of Tim Timmons.” (39:54)

10. Embracing New Skills for Roles (41:28 – 44:04)

• “You just dive in and focus. That’s the good, fun, and joy of being an actor, being an artist...I get to live another existence and soak it up so much that it’s believable on camera.” (43:02)
• On performing stunts, working with military trainers, and learning new crafts for authenticity.

11. Respect for Stunt Performers & Specialized Pros (44:04 – 47:55)

• Bobby and Milo trade stories about dangerous stunts and having renewed respect for professionals behind the scenes:
  • “You leave that with not only a skill set, but with a whole new respect for what people [do].” – Bobby (46:07)
  • “To know that there’s another human being behind that person...stunt performers are always hidden because that’s the job...that bravado of the stunts, you’re like, bro, that wasn’t you.” – Milo (46:38)

12. Memorization & The Actor’s Craft (47:55 – 49:07)

• Milo’s routine: reading, writing, and repeatedly transcribing lines to “flex the muscle”.
  • “It’s like a muscle, you know, that gets flexed...For me, I gotta be old school.” (47:58)

13. Ad Lib, Script Fidelity, & Filmmaking Approaches (49:21 – 51:49)

• The “rules” for improvisation depend on the filmmakers, not the medium.
  • “Brent McCorkle is such a talented writer that the words stuck...But the way Tim is...I’d find little moments to go touch off script and add something that’s very Timmons into the scene.” (49:50–50:24)
• Sometimes strict adherence is needed; other sets invite the actor’s interpretation.

14. Watching Yourself Onscreen and Growth (52:18 – 54:10)

• Milo admits he is usually highly self-critical but, for the first time, found himself able to just watch and enjoy his performance at the big-screen premiere:
  • “I was not as critical of myself. I could actually watch and experience what movie Tim was going through.” (52:20)

15. Fatherhood, Adversity, and Personal Growth (54:10 – 60:14)

• Bobby shares impending fatherhood anxieties; Milo offers advice:
  • “You can prepare. You can’t plan because your plans will change. And, by the way, your kid is in charge.” (54:39)
  • On learning the four cries: “When they’re infants, all four of those are so distinct.” (55:00)
  • On hardship: Losing a house to fires two weeks before his daughter’s birth, cross-country travel: “It was just hard. It's a bit of a blur...but when I look back...it's just fun to revisit. Those first couple months are hard, man.” (58:10)
• Perspective on parenting later in life: “Now my life is good...I didn’t think life could change as drastically as it just has. But...I wouldn't give it up for anything.” (59:57)

16. Skincare, Health, and Aging in Hollywood (60:14 – 61:40)

• Milo (age 48 at daughter’s birth) jokes about looking 31 and shares his skincare and health routine:
  • “Moisturizing. Good living, I guess. Don’t drink, don’t do drugs, try and stay healthy, eat well.” (60:22)
  • On weight fluctuations for roles and the basics: “Moisturize, sunscreen, drink a lot of water.” (61:06)
  • Importance of sleep and hydration.

17. Resilience, Gratitude, and Overcoming Rejection (62:44 – 64:55)

• On dealing with rejection and finding gratitude:
  • “Early days, probably about 99 no’s before I get a yes...as years march on, maybe about 60...but still, it doesn’t change my work ethic approaching it. I’m grateful to be here.” (63:20)
  • On holding grief and gratitude together: “Understanding that two things that are completely opposite can actually coexist at the same time. Whatever is presented to us...you're able to get through it.” (65:04)

18. Authenticity and Set Culture (66:42 – 67:22)

• Bobby praises Milo’s warmth and authenticity off-camera:
  • “Yours was awesome. It was extremely warm, very instantly kind...just a delight off camera, too.” (66:57)
  • “I was thinking you actually do live that [ethos], because when you entered the room, it felt like that with you.” (67:22)

19. Trace Adkins Stories and Hollywood Outsider Moments (67:23 – 72:31)

• Colorful stories about Trace Adkins, Nashville vs. “Hollywood kid” dynamics, and bonding over adversity:
  • “I heard your house burned down. Mine burned down, too. And that was it. And, like, after that, dude, he was my boy.” (69:09)

Notable Quotes (with Timestamps)

• On Will Smith’s set etiquette:

  "What I saw on that set was kindness and inclusion from him... I learned that from Will. Early days." – Milo (05:16)

• On the ending of This Is Us:

  "By the end, you realize, oh, wow, it's about mom... a beautiful love letter to the strength of women." – Milo (02:38)

• On acting’s emotional core:

  "We’re emotional professionals. But you don’t know the successes with it. It could be the most feeling show ever, and nobody watches. That’s how it goes." – Milo (27:24)

• On resilience:

  "Holding gratitude and grief together...two things that are completely opposite can actually coexist at the same time." – Milo (65:04)

• On parenthood:

  "You can prepare. You can’t plan because your plans will change. And, by the way, your kid is in charge." – Milo (54:39)

Memorable Moments & Humor

• Milo’s party guest #2 line from Fresh Prince:

  "Relax, Ash. We’re just taking a little tour." (04:41, callback to early acting days)

• Learning fighter pilot “chirping”:

  "The physical chirp... You’re doing Lamaze right now. Boom. There’s a child." (16:28)

• On learning to play, sing, and drum at once:

  “He would teach me, like, 12 ways to play one note. I’m like, bro, give me one way to play it.” (38:37)

• Trace Adkins’ boots story & the ‘Hollywood outsider’ in Nashville:

  “I don’t know about this Hollywood kid... after the first couple days of filming... he was my boy.” (69:09)

Timestamps for Major Segments

• 01:41 – “Most asked questions” about This Is Us, Fresh Prince, and his name
• 13:18 – Fighter jet stories (“chirping,” passing out at 8.5 Gs)
• 19:30 – Military/military support experiences
• 24:36 – First major “yes” acting moment
• 26:43 – Cultural impact of This Is Us and TV fame
• 33:34 – Preparing for I Can Only Imagine 2, playing Tim Timmons
• 41:28 – Challenges of new skills for acting
• 44:04 – Stunt stories and newfound respect for specialists
• 47:55 – Memorization techniques for actors
• 49:21 – Script fidelity, ad-libbing, and working with directors
• 52:20 – Watching your own performances
• 54:10 – Fatherhood advice and adversity
• 62:44 – Handling rejection and gratitude
• 66:42 – Milo’s authentic, welcoming energy noted by Bobby
• 67:23 – Trace Adkins anecdotes and ‘Hollywood outsider’ moments

Tone & Language

Warm, humorous, candid, and grounded. Milo is reflective, humble, and stories are told with vivid, conversational flair. The episode is packed with life advice, practical lessons, and an authentic, accessible look behind-the-scenes—both in Hollywood and in real life.