New Rory & MAL: "Checking In With Trevor Jackson"

Release Date: October 2, 2025
Guest: Trevor Jackson
Hosts: Rory & Mal

Episode Overview

This episode of New Rory & MAL features multi-talented performer Trevor Jackson, known as a singer, songwriter, actor, and former child Broadway star. The conversation covers Trevor's new music, especially his breakup-themed EP "I Love You," the journey of growing up in the spotlight, lessons learned from showbiz, navigating acting and music careers, his new role on Grey’s Anatomy, and deeper reflections on self-worth, therapy, and creativity in a world shifting toward AI.

Key Topics & Insights

1. Trevor’s Latest Project: The "I Love You" EP and Album

• Trevor is releasing a new EP, "I Love You" (out October 3), as the first part of a series leading up to his breakup album, I Love You, Goodbye.
• Authenticity: The album was written in the wake of a breakup and a major surgery (Achilles tear), with raw, immediate emotion.
  • "I wrote it so close to my breakup in such an honest way." — Trevor Jackson [03:54]
  • "It was the quickest album I've ever made. I wrote the album in like two and a half weeks." — Trevor [10:28]
• The last words from his ex ("I love you, goodbye") became the project's theme.
• Trevor shares he takes accountability for his role in the relationship:
  • “Nobody did one thing or the other. It just wasn’t right… where I am now, I would go through the pain again a million times.” — Trevor [05:15]

2. From Child Star to Versatile Artist

• Trevor recounts performing as young Simba in The Lion King on Broadway at only 8 years old.
  • “My mom knew, and she had a dinner at my grandmother’s house… She’s like, ‘We’re going to have to leave soon because you’re going to be in The Lion King’… and I felt like we did it.” — Trevor [07:46]
• He attributes his grounded nature to family support, never creating "for anybody’s approval." [06:19]

3. Navigating Music and Acting Careers

• Trevor pushes against being boxed in as an "R&B artist," seeing himself as a global, genre-bending musician.
  • “My goal is to not be R&B... I want to make music that... promotes freedom with everything that I do.” — Trevor [09:56]
• Describes music as more personal than acting, emphasizing it's his "therapy" and source of healing.
  • "When I’m acting, I’m acting as someone else… but if I’m writing my music, it’s so personal and it’s so real. And it saved me." — Trevor [10:28]
• Discusses challenges of finding his own sound after being signed young and molded by industry expectations.
  • “I had to find my voice… I wouldn’t change anything, man.” — Trevor [13:11]

4. The Reality of Growing Up in Showbiz

• Trevor addresses missing out on moments of gratitude when younger but now reflects on it with maturity.
  • "When I was younger... there was a time where I wasn’t as grateful as I should have been in the positions that I was at... I get to do those things, I don’t have to do those." [19:26]
• The hosts discuss the pressure to pick one talent, with Trevor embracing his multi-faceted identity.
  • “Why in any other field... is that different? I can sing just as good as I can act.” — Trevor [18:32]
  • “There’s a such thing as being too talented… sometimes people are kinda like, ‘pick one.’” — Rory [18:42]

5. Therapy, Accountability, and Black Masculinity

• All agree on the importance of therapy—especially for Black men—removing the stigma of seeking mental health help.
  • "It’s almost like you’re saying something’s wrong with me."
  • "It’s cleansing the mind..." [21:24-21:46]
• Trevor credits therapy and self-reflection for resilience and not letting the industry destroy his sense of self.

6. Acting on Grey’s Anatomy & More

• Trevor joined Grey’s Anatomy, not out of long-term planning but through a successful audition.
  • "When it happened, I'm like, whoa, this is sick." — Trevor [22:12]
• He shares behind-the-scenes medical training stories—learning to suture bananas and the humbling challenge of faking expertise on set. [23:14]
• The group jokes about actors’ ability to “act” in real life, impact on relationships, and the line between authenticity and performance.
  • “You literally lie for a living. Like, how can I believe anything you say?” — Trevor (on dating, reflecting women’s suspicions) [24:34]

7. Superfly, Missed Roles, and Brand Alignment

• Discussed the Superfly remake, not getting a sequel, and why Trevor sometimes passes on potentially iconic roles to avoid being “boxed in” (like being "the Superfly guy" or playing Michael Jackson). [14:35-15:17]
• No regrets on roles missed: “There’s none that I… yeah, it’s the opposite… a lot of ones that I wish I’d gotten, and I’m glad I didn’t get it.” — Trevor [15:31]
• Expresses caution about protecting his brand and long-term vision.

8. Collaboration & Role Models

• Trevor names frequent collaborators (his brother Ian, producers, Eric Bellinger, Mike J) and aspirations to work with Drake, Wayne, Rascal Flatts, and writes about his process:
  • "I wrote probably 90% of the album." [33:31]
  • “Sean Stockman from Boyz II Men… That was another shoutout. Bro, you’re doing everything… keeping it alive.” — Trevor [34:48]

9. Reflections on R&B, Creativity & Vulnerability

• The state of R&B—considered “niche” now—mirrors society’s skepticism about effort and authenticity.
  • “Today’s society, effort is frowned upon, which I hate… it’s not cool to try.” — Trevor [43:44]
  • Encourages listeners to invest fully in things they love despite peer pressure or trends.

10. On AI/Technology's Impact on the Arts

• The hosts and Trevor reflect thoughtfully (and with concern) on AI's potential to infiltrate even pure art forms like Broadway.
  • “You’re not even gonna know… They’re gonna look like us.” — Trevor [48:23]
  • “AI signed to a $3 million deal... that's laundering!” — Mal [49:34]
• Despite this, Trevor finds motivation to go even harder as an artist: “I don’t feel like a robot could write a breakup song that would feel like these…” [51:01]

11. Lighthearted & Personal Moments

• Trevor shares he struggles to "sit still"—joking about possible anxiety (“I found, as I got older, it could be anxiety… I was always singing, and… it calms it.” — Trevor [46:46]).
• The group jokes about life as multi-talented Black men, therapy, dating as an actor, and Trevor’s real-life experiences meeting Lil Wayne. [46:23]

Notable Quotes & Memorable Moments

• On writing the album:
  “I wrote it so close to my breakup in such an honest way.” — Trevor Jackson [03:54]
• On accepting pain:
  “I would go through the pain again a million times.” — Trevor Jackson [05:15]
• About his Broadway call:
  “I’m running up, grabbing, jumping on her… I felt like we did it.” — Trevor Jackson [07:46]
• On authenticity in his art:
  “I don’t create for anybody’s approval.” — Trevor Jackson [06:29]
• On acting vs. music:
  “If I’m writing my music, it’s so personal and it’s so real. And it saved me.” — Trevor Jackson [10:28]
• On versatility:
  “Why in any other field... is that different? I can sing just as good as I can act.” — Trevor Jackson [18:32]
• On therapy for Black men:
  “It’s cleansing the mind. It’s... just like taking a shower.” — Trevor [21:43]
• On R&B today:
  “Effort is frowned upon… it’s not cool to try… but it’s okay to put everything you have into things you love.” — Trevor Jackson [43:44]
• On AI in the arts:
  “I don’t feel like a robot could write a breakup song that would feel like these…” — Trevor [51:01]

Timeline / Key Segments

• [02:22] – Trevor Jackson introduction, new music, I Love You EP details
• [03:54] – Writing through heartbreak, inspiration for the album
• [06:19] – Childhood in showbiz, family support, authenticity
• [07:46] – Booking Lion King as Young Simba, family reactions
• [10:28] – Why music is therapeutic, making the album after injury and heartbreak
• [13:11] – Industry pressure, finding his own creative voice, collaborators
• [14:35] – Discussion of the Superfly remake; career decisions & typecasting
• [18:32] – Embracing multi-disciplinary art, societal pressure to "pick one"
• [21:24] – Therapy, especially for Black men, and overcoming stigma
• [22:12] – Scoring Grey’s Anatomy role, prepping for TV medicine
• [24:34] – On dating as an actor and trust issues
• [33:31] – Creative process, collaborators, and narrative arc for the albums
• [43:44] – On effort, R&B, group conformity, vulnerability in today’s music scene
• [48:16] – Deep-dive: can AI ever replace pure live art forms like Broadway?
• [51:01] – Why AI can't write “real” songs; renewed motivation

Episode Takeaway

Trevor Jackson’s conversation is a compelling look at the realities of being a multi-faceted Black entertainer in today’s world: the joys and pain of creative honesty, maturing in the industry, the hand-in-hand nature of therapy and artistry, and the challenge of innovating while preserving soulfulness in an increasingly AI-dominated world. The chemistry among Trevor, Rory, and Mal brings humor, vulnerability, and practical insight to listeners—whether you're a fan of Trevor’s multifaceted talents, navigating your own creative path, or just seeking inspiration.

Release Reminder:
Trevor Jackson's EP I Love You drops Oct 3, with the album I Love You, Goodbye to follow in November.