Actor Malik Yoba spent his childhood in Harlem, N.Y. absorbing accents while riding the subway. Transportation became education for Mr. Yoba, who embraced the people he observed as inspiration for character work throughout his career in Hollywood.

On Saturday, August 19, Mr. Yoba introduces more than a dozen of his characters to an audience at the Tabernacle in Oak Bluffs as he performs his one-man show Harlem to Hollywood, promoted by The August Wilson African American Cultural Festival.

Beyond his 30-year career acting in film and television, Mr. Yoba is a writer, producer, director and musician. He said that developing his show was an act of artistic freedom that allowed him to exercise the breadth of his creative abilities and imagination.

“I call it my opus because I’ve always been a multi-hyphenate,” he said. “The journey of the artist — particularly an entrepreneurial artist — is that you’re always looking to create your own space.”

“The actor in me, and the songwriter and musician, has a lot of stories to tell, but no one is hiring you to tell those stories,” he continued. “To me, in many ways this represents a mic drop. After 30 years in Hollywood, you get frustrated with people telling you what you can and can’t do creatively.”

Set in a therapist’s office, Harlem to Hollywood is filled with scenes of vulnerability, humor and creativity as Mr. Yoba uses his characters to divulge his journey from childhood through his career.

At the same time, the show explores themes of fame, love, loss, abuse, relationships, spirituality, family and self-acceptance, he said.

“As a Black man that’s been in therapy since my early 20s, I’ve always felt it was important to give permission to other Black men specifically to do that inner work,” he said.

Mr. Yoba’s inspiration for becoming an actor came from the first play he ever saw at four years old: Alice in Wonderland. His enduring love for the play is evident in Harlem to Hollywood, as Mr. Yoba was influenced by Alice in Wonderland’s psychological, psychedelic and surreal aspects in his approach.

The play warps reality and fantasy with past and present, creating a metaphor for Hollywood and an exploration of the self.

“You have this dream of going to this place, but then you fall down the rabbit hole and meet all these crazy characters and have to find your way out of that,” Mr. Yoba said.

Having performed Harlem to Hollywood since 2018, Mr. Yoba typically emphasizes the play’s dreamlike atmosphere through avant-garde audio/visual elements. The Tabernacle performance, he said, will be a more unplugged version of the show. Having developed the play over 20 years with the show’s director and co-writer Kevin Ramsey, Mr. Yoba said he strives for a TEAR experience: “a performance that is transformative, emotional, authentic and relevant.”

“If you hit the high note, make them laugh, give them something to think about and give them hope, if you give each of those touchpoints, you will win every single time,” he said.