Roc-A-Fella Records founder Dame Dash has been dominating the headlines this week after his explosive September 16 interview with Charlamagne Tha God on The Breakfast Club. Dash, who made a name for himself as an entrepreneur and music executive in the late 1990s and early 2000s, was clearly agitated and accused Charlamagne of being gay when questioned by the veteran radio host about the size of his bank account.
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Now, as memeworthy clips of the conversation are hitting every corner of the internet, some are wondering how someone who was responsible for helping launch the careers of some of the most well-known rappers in the industry got to this moment. We’re looking back at how it all started.
This is the story of Dame Dash.
Harlem Beginnings
Damon Dash was born in Harlem on May 3, 1971. Growing up, he says he learned the value of hard work from his mother, who passed away when he was 15 years old.
“I owe everything I am to my mother,” he told The Guardian in a 2005 interview. “She gave me the best of everything and inspired me to get the best out of life.”
The Rise of Roc-A-Fella
In 1994, Dash started Roc-A-Fella Records along with Kareem “Biggs” Burke and Shawn “Jay-Z” Carter, a then undiscovered Brooklyn rapper who (believe it or not) no other record label would sign at the time. The three launched the label with Jay’s classic 1996 album “Reasonable Doubt,” and went on to become a force in hip-hop, adding artists like Memphis Bleek, Beanie Sigel and eventually, the rapper formerly known as Kanye West to the roster.
Dash says he saw the record business as a legal alternative to selling drugs that would allow him to be his own boss.
“To be honest, I was trying to find an alternative to selling drugs, because selling drugs was not sustainable. I didn’t see a future in it,” he said in a 2022 interview with Notion. “So I wanted to find a way to make money, and still be a boss, but I didn’t want it to feel like traditional work where I’m just doing what I’m told and not being creative.”
Roc-A-Wear and More
Dash hit his stride as an entrepreneur in the late 1990s with a series of major deals. In 1997, Roc-A-Fella sold a 50 percent stake in the label to Island Def Jam for $1.5 million. The brand also expanded to include the Rocawear clothing line and Roc-A- Fella Films.
Roc-A-Fella Fallout
Dame Dash, Jay-Z and Roc-A-Fella were on roll, until things began to fall apart. A decade after the launch of their label, the company renewed its contract with Def Jam for $20 million. Def Jam purchased the remaining 50 percent of the label and Jay-Z was named Def Jam’s President and CEO.
Jay-Z was excited to take on his new position.
“I have inherited two of the most important brands in hip-hop, Def Jam and Roc-a-Fella,” he said when the announcement was made. “I feel this is a giant step for me and the entire artistic community.”
But Dame was less than thrilled. He was upset that the deal had gone down behind his back, and he made his feelings known in a famous in-office rant that was caught on camera.
“Y’all should have called Damon Dash, make sure I was privy to it and made sure I was cc’d or whatever,” he said.
The Trouble With Jay-Z
But when asked for his side of the story, Dame said the reason his relationship with Jay ended had nothing to do with business.
In an interview with Nick Cannon, Dash said he ultimately chose to cut things off with Jay-Z when he chose to collab with R. Kelly, who was previously romantically linked to Aaliyah, on “The Best of Both Worlds” album and tour. Dash said the singer confided in him that R. Kelly sexually assaulted her, something he felt was dealbreaker.
“You gotta ask me, ‘How do you deal with that when someone you respect does some s*t that you don’t f* with at all, right?” Dash told Cannon.
All About The Ego
Of course, other people had their thoughts about what made Roc-A-Fella fall apart. In an interview with Shannon Sharpe, record executive Steve Stoute said Dash’s biggest problem in business is his ego.
“Dame wouldn’t change. The way he spoke to people. The way he treated people. He was angry,” he said. “Ego through the roof, so there was no working with him. As much talent as he has, no one wanted to work with him.”
Meeting Aaliyah
It’s hard to talk about Dame Dash without mentioning his relationship with the late R&B singer Aaliyah. Dash said the two first met through his bookkeeper. Aaliyah was also a client. But he added that, at least for him, it wasn’t exactly love at first sight.
“When I first met her, she was like a kid to me, so I never paid her no mind,” he said in an interview with Julian Keyz. “I wasn’t listening to her music or any of that.”
Shooting His Shot
Eventually, he knew she was someone he wanted to be with. The only problem was practically every other man in her orbit wanted to shoot their shot too. In interviews, Dash has alleged that Jay-Z also had his eyes on the “Try Again” singer.
“Everybody was going at Aaliyah. That’s why it hurt so much when I was the one that got to get with her. I wasn’t thinking that I was gonna fall in love, but she was just too ill, too cool,” he added.
Dash and Aaliyah dated from 2000 until she tragically died in a plane crash in 2001.
Marriage to Rachel Roy
In 2005, Dash married designer and former Rocawear intern Rachel Roy. The creative couple launched her ‘Rachel Roy’ fashion brand in 2008. But when their marriage ended in divorce in 2009, Dash and Roy entered an intense legal battle over the business and for custody of their two daughters, Ava and Tallulah. Roy eventually secured custody in 2015 and a three-year restraining order against Dash.
Legal Trouble
Dame Dash’s business dealing left him in a lot of legal trouble, and he became the target of a lawyer by the name of Chris Brown. Brown represented a production company who was suing Dash for defamation for attempting to put his name on a project he wasn’t involved with. Dash lost the case and was ordered to pay a settlement of over $700,000. When he refused to pay, it triggered others to come after him for debts he owed, including back child support and unpaid taxes. Before long, Brown represented a group of people who were coming after Dash for money.
“Every time I would launch something with my family office, he sends a letter saying I owe the money,” he told The Breakfast Club.
Going for Broke?
These days, rumors have been swirling that Dame Dash is not the baller he was in the early 2000s. PEOPLE reported that Dash filed for Chapter 7 bankruptcy on September 4, claiming he is more than $25 million in debt and has just over $4,000 of cash to spare.
But Dash has gone on record defending his decision, saying it was a move to protect him from being sued.
“I wanted it as much publicized as possible, because I want people to learn something about this,” he told The Art of the Dialogue. “This is when I do want you in my business, because when you file, you got to tell them everything… But all the people you owe money to, they’re not allowed to sue you.”
He adds that filing bankruptcy was in the best interest of his family, for whom he’s trying to leave a legacy.
“I can’t get a job to pay [the taxes] back. I’ve got to keep investing until I can pay it back. Nothing can be in my name. They put liens on all my accounts years ago. I have no assets but my family, that’s all I care about,” he told The Breakfast Club.
Making Rock and Roll With A “White Aaliyah”
Dame Dash has hit the reset button on his music career, this time with his rock band, Freeway x The Black Guns, who dropped their debut album, “365,” in June 2025. One of the members, Nicky Licky, has been appearing with him in interviews, and folks can’t seem to stop talking about the strange comparison he’s making to her.
“It’s funny because you know, to me, she’s like if Aaliyah was White. If Aaliyah was White, she’d be a lesbian. That’s her and she has the same everything,” he said, opening her jacket to show off the crop top she was wearing underneath.
But Dash’s comments about his new artist didn’t sit well with Aaliyah fans, who were offended by the mere suggestion.
“Ain’t no way dame compared that vanilla wafer to Aaliyah dame has officially lost his mind,” wrote someone in the comments.
Chairman of Revolt?
During his September 16 interview with The Breakfast Club, Dash told the hosts he was giving them the exclusive on his latest business deal – becoming the chairman of Revolt, the multi-platform media company founded by Sean “Diddy” Combs in 2013. Dash also used his announcement as an opportunity to take a dig at rapper Cam’ron, who hosts Revolt’s “Talk With Flee” podcast.
“I’m now Cam’s boss, the Chairman of Revolt, with a pathway to acquisition,” Dash told The Breakfast Club hosts.
But shortly after making the announcement, listeners were left scratching their heads when TBC host Loren Lorosa followed up with the folks at Revolt who told her that Dash’s statement was not true.
“I just spoke to a lead publicist at @revolttv who confirms to me .. Dame Dash is not the chairman of the network,” she posted on X on September 16.
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