This week, we are talking di tings with Jamaican-American Actress and Author Sundra Oakley.

Sundra’s 20+ year career embodies both artistic excellence and cultural integrity.Although she is highly regarded for her portrayal of renowned attorney & Bob Marley’s close friend, Diane Jobson in Bob Marley: One Love and her role as Theodora in the acclaimed Hulu series Washington Black, she has also had roles in Sex and the City, Parenthood, and The Resident, to name a few. Sundra is a graduate of the prestigious NYU Tisch School of the Arts, fluent in multiple languages, and trained in martial arts, dance, and yoga; enabling her to bring intellectual depth and discipline to every role she plays. 

Rooted firmly in her Jamaican heritage and guided by authenticity, Sundra has become both a cultural ambassador and a vital mirror for representation, ensuring that Caribbean voices and stories are seen, heard, and celebrated. 

She continues to inspire the next generation through public speaking and her mentorship workshop Inside Hollywood: The Business of Being an Actor, which equips Jamaican talent with the tools to navigate the entertainment industry.

In this episode, Sundra reflects on her personal and professional journey. From being a shy child to emerging as a celebrated and respected Actress. She reflects on the role that trust, community, and representation have played throughout her life, shares what it meant to play Diane Jobson, the power of showing up as your true self in an industry that often rewards imitation, the responsibility that comes with being a mirror for Caribbean women; whom we both strongly believe deserve to see themselves reflected on screen, the power of intention, and so much more!

This episode is an invitation into the richness of Caribbean culture, the versatility of Caribbean women, the discipline of growth, the transformative power of storytelling as a tool for belonging, visibility, and legacy; and why yuh nuh fi chat people business lol. 

So grab your tea, coffee, or a glass of wine, and let’s talk di tings! 
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