In this episode of If You Knew Better, Amber Grimes sits down with Lil Rel Howery for an inspiring conversation about building a lasting career in entertainment through persistence, purpose, and creative evolution. Rel reflects on the moment he realized he'd truly "made it" in film and television [00:46], then looks back to the high school performance that first showed him he could win over even the toughest audiences [02:04]. He shares how directing became part of his journey after encouragement from Bobcat Goldthwait [03:29], the lessons he learned making his directorial debut [06:19], why collaborating closely with every department shaped the experience, and how casting friends and fellow comedians—including support from Tiffany Haddish—helped bring his vision to life [07:56]. The conversation also explores his love of horror-comedy [11:00], how comedy continues to evolve alongside audiences [13:46], and the way grief and personal experiences have informed both his work and perspective [16:47].

Rel also discusses the importance of inspiring the next generation to understand the many career paths available in entertainment [19:10], the values instilled by his parents through community service and mentorship [22:46], and the filmmakers who inspired his own creative ambitions, from Steven Spielberg [27:08] to the lessons he drew from Sylvester Stallone and Rocky [29:04]. He explains why studying the business has been just as important as mastering the craft [30:37], the unique challenge of acting while directing [32:34], and how he now defines success through personal milestones like Get Out and his Chicago Theatre special [33:54] [36:36]. Closing on a reflective note, Rel shares how he stays grounded and present [43:53], the wisdom and healing that have shaped this stage of his life [47:07], and previews his new horror-comedy Haunted Heist, arriving in theaters on July 24 [50:50].

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