Multi-hyphenate talent O’Shea “Ice Cube” Jackson got his big break in Hollywood when he starred in the cult classic “Boyz N Da Hood” over two decades ago.

The film is a coming-of-age story set in South Central Los Angeles. The film stars Cuba Gooding Jr., Morris Chestnut, Laurence Fishburne, Angela Bassett and other actors who have become household names.

But while the story of three Black teens choosing their path in life — one pursuing a collegiate football career, another the gang life and the last uncertain of which way to go — was perfect for a young Jackson, he nearly missed out on his big break.

The former “N.W.A.” member recalled his introduction to the film taking place in the late ’80s when he encountered the film’s creator and director, John Singleton. Speaking with rapper Gillie da King and social media influencer Wallo267, Jackson said the first of several chance encounters occurred while he was at the “Arsenio Hall Show.”

“Dude walk up to me, he’s an intern, he’s like ‘Yo man you in N.W.A. huh?’ I’m like ‘Yeah’ …this is before we were famous like household names, and so I’m like ‘Yeah, yeah,’ ” explained Jackson on the Monday, July 26, episode of “Million Dollaz Worth of Game” podcast.

“You know, he’s like ‘Man, I got the perfect movie for you dude.’ I’m like ‘What? You got the perfect movie for me?’ I’m like for one I’m not an actor so I’m looking at him like he crazy because it was just unusual for someone to walk up to a rapper talking about ‘I want you to act’ back then, so I was like ‘whatever man.’ So he was just telling me about the movie, he actually wanted all of us in the movie — he wanted Eazy in the movie, Dre and them — and I guess he said he ran into them but they didn’t take him serious. At that time I didn’t take him serious, I was like ‘all right man; that’s cool.’ ”

He continued by explaining that months later he again ran into an ever-determined Singleton who excitedly told him he still wanted him to star in first feature film. “He walked up to me saying the same stuff you know, ‘You perfect man. I’ma junior at USC man [University of Southern California] but dude when I graduate I’ma put you in this movie,” recalled the “F—k the Police” emcee.

A year goes by and again Jackson is confronted by the eager future filmmaker, who continues to insist that he will put the rapper in his movie. “He’s like, ‘Remember me?’ I’m like, ‘Dude I’m seeing you like every six months, every year-and-a-half; yeah I remember you.’ He’s like, ‘Yeah, I’m a senior now at USC, man you perfect for this movie. Can I tell you about it?’ ” Still not sold on just how serious Singleton is about this movie, Jackson obliged him.

“So I’m like,” he said with an exasperated sigh, ” ‘tell me about it.’ So he tell me about the movie. I’m halfway paying attention and I look around and everybody leave, the place is empty, parking lot empty, it’s just me and him in there. He asked for a ride to his dorm, I’m like, ‘D—n, d—n n—-a I just met you and you want a ride!’ I end up dropping him off and I’m like man if I don’t see that dude again, man you know he keep telling me the same story.”

But that wasn’t the end of the story for Jackson and Singleton. By this point another year had passed and Singleton had graduated. For Jackson, the eager college student and his film were out of sight and out of mind. Until it wasn’t. The year was 1990 and Jackson still uninterested in acting was presented with a script from his manager Pat Charbonnet. Unbeknownst to him it was the script to the very movie he’d been blowing off for the past three years.

“I threw that script in my backseat, put the paper in my pocket, just went on to the house. So on Thursday I show up, I pull the thing out my pocket, I read the little lines, I go in there and I think I’ma see these white people in here to make this movie that they want me in. I don’t even know what it’s about. I walk in it’s John there,” said Jackson while recalling how dumbfounded he was in the moment.

He continued, “He [Singleton] was sitting there saying, ‘Remember me?’ and I said, ‘D—m you!’ He said, ‘I told you I’ma put you in a movie. I’m gettin’ my movie made, I want you to be in it. You ready to audition?’ I’m like, ‘Yeah.’ ” But Jackson was anything but prepared. He hadn’t taken the script or the audition serious and, as a result, it showed in his performance. “So I go audition and I’m terrible. I mean I suck. I’m reading it. I can’t get the flow and he just look at me like man.”

“He said, ‘Everybody leave.” He put everybody out. He say, ‘Cube, man, that was terrible. Did you read my script?’ ” I said, ‘Nah, I ain’t read it man. I didn’t even know it was you. I thought it was some white people gon’ be in here.’ He said, ‘Man go home, read my script and come back. I’ma give you one shot at this, man. I’ma give you one more shot. I hope you better than you was today after you read this.’ ”

When Jackson went home he finally gave the script a thorough read. Finally realizing the story of “Boyz N Da Hood” and the parallels of his own upbringing shared to the storyline, he was ready to nail the audition. And he did. In the film that grossed almost $60 million at the box office, Jackson plays Doughboy — a teen accepting his fate as a gang banger destined to see the inside of a penitentiary as his brother Ricky goes on to play football at USC; though the latter tragically would never happen.

For his debut film, Singleton became the youngest person and first African-American person to be nominated for Best Director at the Academy Awards. He would go on to make more iconic films such as “Poetic Justice,” “Higher Learning” and “Baby Boy.”
Jackson’s acting career took off just as his career as a screenwriter and producer did. The first film he co-wrote, “Friday,” also became a cult classic in the Black community, and even spawned two sequels.

In 2019, Singleton passed away at the age of 51. The acclaimed director died after suffering a stroke upon returning from a trip to Costa Rica. “I just miss him,” said Jackson. “That dude became my mentor in the game, helped me actually become a screenwriter. He helped me direct, he helped me produce. Every time I needed some advice, I would call him because he went to school and went through all this. I didn’t go to none of that stuff so I would lean on him, and he was always gracious, and I miss that dude.”