Michael Rapaport’s acting career goes back nearly 30 years. In an array of roles, one of his most memorable is that of 1995’s Higher Learning. In the John Singleton film about college and diversity, Rapaport played “Remy,” a student who transforms into a skinhead. However, that role was first attached to future Oscar-winner Leonardo DiCaprio, while Rapaport was signed on to play another part. Similarly, Omar Epps’ protagonist “Malik Williams” was first intended for Tupac Shakur. At least one other future marquee star was tied into Singleton’s third feature film.

Michael Rapaport now explains how everything changed ahead of shooting. Of the “Remy” part, Michael tells DJ Vlad, “[Leonardo DiCaprio] didn’t lose the role. Like, [Higher Learning] was originally [starring] Tupac [Shakur], Leonardo DiCaprio. It was originally Gwyneth Paltrow in the Jennifer Connelly [character of ‘Taryn’]. I was gonna be [the ‘Scott Moss’ character eventually played by] Cole Hauser. Tupac had to pull out of the film because the [studio] wouldn’t finance the film, ’cause he had gotten arrested.” In 1993 and 1994, Shakur had a number of incidents with the law, ranging from assault, shooting to sexual assault charges. “So when Tupac dropped out, then Leonardo dropped out, and Gwyneth dropped out. I mean, this didn’t like happen in a day; it happened like over a period. Nobody was locked in; I think Tupac was locked in. People were sort of circling around the film; this is two or three months out [from the beginning of shooting]. So it wasn’t like, ‘Tupac’s out, I’m bailing.'” Paltrow, who won an Oscar for Shakespeare In Love, was replaced by Connelly—a winner for A Beautiful Mind.

“DiCaprio’s path was going to be his path; we all knew he was gonna be mega. He had done [What’s Eating Gilbert Grape and This Boy’s Life] and you just knew,” continues Rapaport. “So when Tupac pulled out—who you knew was special too—but the trouble had already started—then [the others pulled out]. Then I switched over to Leonardo’s [‘Remy’] role, which was my idea. I wanted it. It turned out good. He wasn’t there, and I always felt I wasn’t totally right for the part that Cole Hauser played [as] the older skinhead. I’d have to put on weight. I was like, ‘I want this part.’ I knew I wanted that part, so I talked to John [Singleton] about it. So he had me come in; it was just me, John Singleton and Ice Cube. He was like, ‘Alright, go ‘head.’ This was before Are We There Yet? Ice Cube; this was when Ice Cube was still with the chipped tooth and sh*t. I was such a big fan of his, and to have come in and do this ‘Remy’ character. He was like, ‘Well, improv’ sh*t.’ Like, he wanted to see if I was ready to do it. And I f*ckin’ was like, ‘F*ck you Ice Cube!’ [and got into character], sayin’ crazy sh*t and just flowin’, and he said, ‘You got the part.’ I said, ‘F*ck yeah,’ and then we made the movie.” John Singleton’s Higher Learning reached theaters in January of 1995.

For those looking for interesting film history and cast changes, AFH has two separate and revealing 2016 interviews on the 25th anniversary of New Jack City with screenwriters Barry Michael Cooper and Thomas Lee Wright.

Further in the VladTV interview, Rapaport also recalls asking Singleton for his cameo in Poetic Justice. The actor, Beats, Rhymes & Life director, podcast host, and author says he wanted to work with Tupac. Prior to their relationship, Rapaport had a lengthy friendship with Jada Pinkett, and knew of the rapper/actor ahead of fame.

He confirms a story told in January by Snoop Dogg, that the future collaborators met in a cypher at the Poetic Justice wrap party, and nearly battled. Rapaport recalls Pac spitting a line akin to “All your homies over there staring at me,” presumably referring to Tha Dogg Pound. Tupac would go on to make a cameo in Snoop’s Murder Was The Case film, and eventually collaborate on several songs, as well as with Daz Dillinger, Kurupt, Nate Dogg, Bad Azz, Warren G, Tray Deee, Soopafly, Swoop G, and Techniec. “I was right there, and I remember [thinking] ‘This is something not to forget.’ I witnessed it with my own eyes. There’s a picture, that night, with me, Tupac, John Singleton, and Ice Cube.” He adds that he photo-bombed them at the time, “‘Cause I wanted to be in the picture.”

Last month, Michael Rapaport and Simon & Shuster published This Book Has Balls: Sports Rants from the MVP of Talking Trash. The New York native also appeared in Snoop Dogg’s controversial “Lavender” music video playing “Ronald Klump.” He is also starring in Netflix family series Atypical.