Why did The Roots reject Redman?

The Roots have gone through a long list of members through the years, with new people jumping in as and when required. They’ve also collaborated with so many great artists.

But certain figures, keen to get involved with the legendary Philadelphia collective, just don’t make the cut. Even some who have gone on to have great careers of their own have, nonetheless, failed to make it into The Roots’ fold, despite their best efforts.

Redman is one such person, who was once desperate to jump onto one of their tracks. He sent them a demo, but it didn’t work out for him. He was left out in the cold.

Redman actually brought this up during a conversation with the group’s co-founder Black Thought in 2025, recorded as part of the Rolling Stone series ‘Musicians On Musicians.’ The two MCs sat opposite one another and had a wide-ranging conversation, but they spoke, at one point, about this potentially awkward situation in which Redman had been jilted.

It was clear that Redman didn’t hold any grudges. While he had been extremely disappointed at the time, there appeared to be no bad blood now. He was even in a reflective sort of mood, offering his use of swearing of his demo as a possible explanation for his rejection. He admitted that maybe he’d been “cursing a little bit too much.”

He acknowledged that he might have said “something derogatory that they probably didn’t like,” but he did add that he “was actually hurt” from the rejection. But Black Thought pushed back, claiming it wasn’t Red’s cursing that had been the problem.

The Roots rapper claimed that the group’s manager had been in control of the situation. This man, the late Rich Nichols, held a lot of creative control at the time, and what he said went. It was Nichols, according to Black Thought, who didn’t want Redman’s contributions.

Describing Nichols as “very much the brains of The Roots operation,” Black Thought insisted that the manager ran “such a tight ship” that even he found it difficult sometimes to “place verses on The Roots’ albums.” Nichols, he said, “would shoot down every submission.”

Black Thought claimed he couldn’t remember specifically what the problem was, but that there was “something that Rich didn’t like about” about Red’s submission. That was that, and Redman couldn’t get on the track. He was hurt because of the rejection, but, clearly, he got over it in the end.