In the canon of artist vs. music executive beefs, Ice Cube’s problems with Jerry Heller are perhaps the most significant. In 1990, N.W.A. soared to the top of the pack, meeting criticism for its profanity and lewdness with massive commercial success. During the quintet’s first national tour, Cube—arguably the lead MC on the Straight Outta Compton album began questioning his contracts and royalty statements from Ruthless Records, and its label co-founders Eazy-E and Heller.

Within months, Cube angrily left the group and launched a solo career that is ironclad more than 25 years later. N.W.A. would release an album, 1991’s Elil4zaggin without Cube. Instead, the group and its former star traded disses. On 1991 album Death Certificate, Cube landed sharp jabs at Eazy, Jerry, and his band-mates through popular diss track “No Vaseline.” At Jerry in particular, Cube rapped to Eazy, “You let a a Jew broke up my crew,” referring to the Cleveland, Ohio native’s religious beliefs. The pair would never make amends.

The D.O.C., Dr. Dre, and others joined Cube in speaking out against Heller’s business practices during the early part of the ’90s. In the middle of the decade, when Cube and Eazy-E reunited at New York City’s Tunnel nightclub, the pair toiled with an N.W.A. reunion. Reportedly, Cube’s condition to return to the group on hiatus was that Jerry Heller would not be involved. As legend has it, Eazy fired Heller shortly thereafter. Sadly, he died in March of 1995—never making the full group reunion possible.

Jerry Heller, Co-Founder Of Ruthless Records & N.W.A. Manager, Dead At 75

In 2015, Ice Cube (along with Dr. Dre and Eazy’s widow, Tomica Woods-Wright) produced Straight Outta Compton. That film dramatized Cube’s conflict with Jerry, as well as Eazy’s firing of his longtime partner. In addition to box office sales records, the film garnered Oscar and Golden Globe nominations. One critic of the film was Heller, who subsequently sued Universal Pictures and film producers for $110 million, the profits from the film, as of February. The exec believed elements of the film were taken from his memoir without permission, as well as his character (played by Paul Giamatti) defamed.

On Friday (September 2), Jerry Heller died at 75 years old .Parties close to him said that Straight Outta Compton‘s affect on his legacy sent him to an early grave. Hip-Hop fans, and those following a 26 year-old storyline would be curious to see what Ice Cube thought of his former manager’s life and death.

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“It’s just ironic that I’m here tonight with MC Ren,” Ice Cube told Detroit, Michigan’s Local 4, who interviewed him on camera. “[I am here] with DJ Yella [too]. We’ve come a long way. And to me, the passing of Jerry Heller is a thing that’s a part of life. You come here to pass away. We all gonna definitely reflect on our time with Jerry. The ups and the downs. And there you have it.” Cube was in Motown performing with some of his former band-mates, as well as Compton’s DJ Quik, MC Eiht, and others.

Detroit was notably the same city where N.W.A. was arrested for performing “Fuck Tha Police” while on tour.

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In his book, Ruthless, Heller wrote in detail about his disdain for Ice Cube, following their conflicts. The two men never spoke following their separation of business. Heller’s lawyer, Mickey Shapiro, told TMZ, that he believes the character destruction of Straight Outta Compton contributed to his death. “Jerry Heller would still be alive today, were it not for that movie,” said the attorney.

In addition to N.W.A., Jerry Heller was deeply responsible for the discovery of artists such as Bone Thugs-n-Harmony, as well as tenures managing Marvin Gaye, Journey, War, and others. He died from complications of a heart attack.