Kendra G, a radio presenter in Chicago, was in Los Angeles for the 50th annual Grammy Awards in February 2008. She was thrilled to be there: Both Kanye West, whose mother had died months earlier, and Amy Winehouse, whose brilliant and brassy album "Back to Black" was up for several awards, were scheduled to perform. On the hunt for a spare ticket for a close friend, Kendra looked to Charlamagne Tha God, whom she had met at a press junket just hours before.

In 2008, Charlamagne was already one of the most influential and controversial voices in New York radio, a polarizing and brilliant sidekick to Wendy Williams on her show "The Wendy Williams Experience." Without much fuss, Kendra said, Charlamagne offered up his ticket, content to miss the ceremony.

The offering marked the beginning of a decades-long friendship. But it also illustrates what has become something of Charlamagne's trademark: a refusal to indulge in the celebrity-driven side of the entertainment industry.

He's an anomaly in hip-hop radio. He isn't from New York, Los Angeles, or Atlanta. He is rarely seen on a red carpet. He is never pictured in the club next to rappers or producers. "All the glitz and glamour is not really his thing," Kendra said. For much of his career, he has described himself as a man of the people rather than of the industry.

But over the past five years, it has become increasingly difficult to detach Charlamagne's success from the mainstream. It's even harder to avoid his presence.

"The Breakfast Club," the boisterous radio show that has both endeared him to and repelled millions of listeners around the world, recently celebrated its 10th anniversary on New York's Power 105.1. Charlamagne and his cohosts, DJ Envy and Angela Yee, are now syndicated on more than 100 radio stations across the US and simulcast on the cable TV network Revolt every morning. In 2020, the trio was inducted into the Radio Hall of Fame.

In December, Charlamagne negotiated a renewal of his contract with the show's network, iHeartMedia. In September, the two launched the Black Effect Podcast Network, which will create audio content for Black audiences and be headed up by Charlamagne. The South Carolina native also established a publishing imprint with Atria Books and signed another audio-production deal with Audible. In the winter, when we spoke for the first time, he was in the middle of prepping a new late-night talk show set to air on Comedy Central this fall.

Today, Charlamagne is no longer the dissenting outsider. Now, in many ways, he is the industry.

More than just 'Hip Hop's Howard Stern'

It's difficult to drill down to the essence of someone's personality over Zoom; there is too much digital space in the way. But that doesn't stop Charlamagne from trying.

As he slouched back on a dark-blue sofa from his New Jersey home, he plonked his laptop just below his chest. The sharp, dark sense of humor was there, but he was much more measured and contemplative than his radio persona. When he talked, he peered at the screen, trying to pin down the sincerity of the questions and the intelligence of the person asking them.

"Fuck a false arrest" - a recent Jay-Z lyric - was written in bold type across his custom sweatshirt, and he wore a fitted hat from the clothing line created by the late rapper Nipsey Hussle.

At the time of our conversation in early March, Charlamagne was in the tabloids again, a once-frequent occurrence. For much of the early 2010s, he was a fixture on gossip blogs and in magazines, usually under the moniker "Hip-Hop's Howard Stern." (He was also partial to the alternative royal titles of "the prince of pissing people off," "the ruler of rubbing you the wrong way," and "the architect of aggravation.")

The nickname came from his talent for doling out controversial tidbits on "The Breakfast Club," like sniffing Jennifer Lopez's seat after an interview. The bravado and bombast was good for business, and "The Breakfast Club" quickly became one of the biggest radio shows, reaching more than 8 million monthly listeners and nearly 5 million subscribers on YouTube.

But even during Charlamagne's most contentious moments, it was clear to anyone who heard him talk that there was an alternative side to his personality - a side shaped by a love for serious literature, a steadfast commitment to fighting racial injustice, and, most of all, a one-of-a-kind gift for interviewing that trumped the talents of Stern and even his cohosts. Over the past five years, that side has begun to take priority.

So when the tabloids latched on to a video that the actor Lakeith Stanfield posted on Instagram - it showed Stanfield waving a gun, apparently threatening Charlamagne in response to something disparaging he said about Stanfield on "The Breakfast Club" - it felt like the Charlamagne of yore for a brief moment. But then he addressed the situation, quickly showing concern for Stanfield's mental health and what he saw as the parasitic nature of the people in the actor's circle.

"Forget the awards. What about him and his mental and emotional well-being? Something's not right there," he told me. "I want the brother to get some help. I want that brother to sit down with somebody." (Representatives for Stanfield did not respond to a request for comment.)

Watching Charlamagne move between these two modes is almost disconcerting. While you're laughing at the joke he made at the beginning of a sentence, he's two steps ahead of you, already dissecting the pain behind it.

This talent for traversing emotional extremes has also been good for business. It introduced him to a larger audience over the past few years as America grappled with the circus of Donald Trump's presidential administration.

Throughout Trump's four years in power, Charlamagne was a mainstay on major news platforms from CNN to Fox, as well as talk shows from Stephen Colbert's to Bill Maher's. He became the voice that white mainstream America used to understand the conditions of Black America. His skill of reeling people in with humor before deftly switching to solemnity allowed him to lampoon Trump's absurdity, while acknowledging the underlying barbarism.

When Joe Biden was attempting to drum up support from Black voters last year, the calls weren't for him to sit down with Oprah Winfrey or Gayle King - people wanted to see him spar with Charlamagne. When Biden did, he came ill-prepared, looking for cheap political zingers in an attempt to engage the old Charlamagne. Instead, he was promptly schooled and later apologized for comments he made during the interview, including the assertion that Black voters "ain't Black" if they were thinking of voting for Trump.

Charlamagne credits this tonal shift with an overall investment in himself that started with therapy, which he now attends twice a week.

"For so many years, Charlamagne was the character that showed up to protect Lenard," he said, referencing his birth name. "I'm not in that space no more. Lenard needed some healing. Lenard went out and got that healing. Now Lenard is fully confident to show up as who he is."

Lenard's beginnings

Charlamagne Tha God was born Lenard McKelvey in 1978 in Charleston, South Carolina, but was raised just north of the city in Moncks Corner, a small, rural town. He's been with his wife, Jessica Gadsden, for 23 years, since high school. He has talked candidly about parts of his private life - including his infidelity - in the past, but he doesn't post pictures of his family on Instagram, and he used code names to conceal their identities in his books.

His radio career began with jobs at several stations in Charleston and then Columbia, a southern hub 100 miles north where the Confederate flag flew from the statehouse until 2015. A mix of early buzz, luck, and ingenuity landed him the sidekick role on Wendy Williams' radio show, which brought him to New York for the first time in 2006. He and many other staffers were fired in 2008, but he rebounded quickly and landed a solo show in Philadelphia called "Charlamagne Tha God and The Morning Beat." He was fired after less than a year, and after a period of unemployment back in Moncks Corner, he landed "The Breakfast Club" in 2010.

Charlamagne's newly renegotiated deal with iHeartRadio is reported to be one of the biggest in syndicated radio, and he maintains a majority stake in his new podcast network. Beyond the numbers, he's also been named iHeartRadio's new senior creative officer of culture content and programming, in which he will curate and program content across the company.

It's rare for on-air talent to be given such a wide-ranging brief. Rarer still is his audience. While the podcast industry continues to expand, the Black Effect Podcast Network remains one of the few podcast labels focused on Black audiences. Charlamagne cited Spotify, which has made substantial inroads in the podcast industry with its acquisitions of Gimlet Media, Parcast, Anchor, Megaphone, and Bill Simmons' The Ringer network, as part of his inspiration.

"I kept saying to myself, 'Man, why isn't there a podcast that's, like, for us, by us? Why isn't there a podcast network that centers around Black voices?'" Charlamagne told me.

While Charlamagne has been one of iHeartRadio's most prized stars for nearly a decade, it's hard to ignore the fact that the company's investment followed a summer of racial uprising.

"Oh yeah, we definitely cashing in on this white guilt, baby. Let's just keep it all the way 100," he said. "And guess what? We deserve it. Guess what? We're owed it."

The podcast network has had 100 million downloads since it launched, according to Conal Byrne, the CEO of the iHeartMedia Digital Audio Group. The launch, however, hasn't been as smooth as the numbers may suggest. At the time of the announcement, there was considerable pushback from fans on social media who said a partnership with a large corporate organization to launch a platform for Black-led content was an act of crude hypocrisy.

Charlamagne waved this off and cited the financial benefits - such as hiring Black staffers - that could come from partnering with a large corporation.

Oh yeah, we definitely cashing in on this white guilt, baby. Let's just keep it all the way 100."

"I fall in line with the ideologies of the honorable Elijah Muhammad," he said, pointing to the leader of the Nation of Islam, "which is the 'do-for-self' model."

Money holds a central position within Charlamagne's activism. He describes himself as a "compassionate capitalist" and says he believes financial freedom is the key to success for Black folks.

This brand of individualism is curious, especially since Charlamagne also spoke about the unforgiving dynamics of late American capitalism in our conversations and the ways in which it intersects with structural racism. When asked about the tension, he pointed to the scholarship fund for Black female students that he set up in his mother's name at her alma mater, South Carolina State University, which is among the US's historically black colleges and universities. He also recounted a story in which he gave a lump sum of cash to the mother of a child he saw playing in the street barefoot during the annual book bag drive he puts on near his hometown. They had only one pair of school shoes and couldn't afford to get them dirty.

"You can't do things like that without any money, sadly," he said. "We're either going to partake in this capitalist society, or we're going to go live like the Amish. I'm with either one, whatever works. I'm just trying to do what works."

Accusations of misogynoir and anti-Semitism

The anecdote is cleverly chosen: There is very little criticism that provokes him, but he takes issue with the suggestion that he holds an apathy toward women - particularly Black women.

This is an accusation that all three hosts of "The Breakfast Club," including Yee, have faced at some point in their tenure. Critics say that while the radio show is known for its controversial antics, the trio's harshest treatment is reserved for Black women.

In 2020, for example, the show was condemned for running a softball interview with the former music executive Russell Simmons shortly after 20 women accused him of sexual misconduct. (Simmons has denied the allegations.) After the interview, Sil Lai Abrams, one of Simmons' accusers, wrote in a blog post: "If you want to reach Black people, you go on The Breakfast Club. But by doing so, a person has to understand that they are going on a show that has shown itself again and again to be anti-Black women yet proclaiming to be pro-Black." In 2017, The Root published an interview with the headline, "Does Charlamagne Tha God Hate Black Women?"

When I mentioned these criticisms, he sat up.

"No. 1, Black women have always been the foundation of my life," he said. "My wife is a Black woman, contrary to the internet's popular belief. I got three beautiful Black daughters. I grew up being a momma's boy, you know what I mean?"

Yet he's often tied to two incidents. The first is an accusation of sexual assault dating back to 2001, the charges for which were later dismissed. (While Charlamagne did plead guilty to the lesser charge of "contributing to the delinquency of a minor," he said he "had no physical contact with the alleged victim whatsoever.") The second is his brief association with Tomi Lahren.

In 2016, he was pictured with the conservative pundit, who had just described the Black Panther Party as a terrorist organization in a widely shared video, outside Viacom's offices in Times Square.

Charlamagne told me that their meeting had been orchestrated by Viacom executives who thought the pair could make the basis of an entertaining talk show. "My mind was like no, 'absolutely not,'" he said about the potential show. "We had a conversation and it didn't take me long to realize that it's a lot of performative aspects to what she's doing." (Viacom did not respond to a request for comment.)

The next day, Charlamagne tweeted that it might be beneficial if a left-leaning woman of color created a popular online platform similar to Lahren's. He was quickly denounced by Black women across the internet, including the comedian Franchesca Ramsey and the writer Jamilah Lemieux, who said they saw his comments as an erasure of their efforts and existence.

I'm gonna be even more intentional about empowering Black women and uplifting Black women.

"It was just stupid. It was just a dumb-ass tweet," he said. "The reason it was stupid was for one reason: All those sisters were there. All those sisters were already out there doing the work ... We weren't doing our part to uplift them."

He described the saga as "The Tomi Tsunami" in his second book, "Shook One," and the moment was perhaps the largest strategic shift of his career. While his talent previously took center stage in his burgeoning media empire, he quickly adapted to focus on uplifting the people he was building with.

"It was just like, all right, watch me, watch what I do now. I'm gonna be even more intentional about empowering Black women and uplifting Black women," he said of the time.

This is now explicitly reflected in the makeup of his business activities. He's quick to point out that the head of his podcast network is a Black woman, Dollie S. Bishop. The first book out of his publishing label is by the activist Tamika Mallory, a cofounder of 2017's Women's March. And the entirety of his personal executive team is made up of Black women.

"I'm never above any of the consequences of my words," he said. "I'm literally just learning as I go."

Last year, he was also entangled in a brief incident involving accusations of antisemitism.

In July, the TV presenter Nick Cannon was fired from his job as the host of MTV's popular improv series "Wild 'N Out" after making several antisemitic comments on his podcast "Cannon's Class." (Seven months later, Cannon and Viacom resumed their partnership and restored him as the host of the series after he apologized.)

At the time, Charlamagne said on "The Breakfast Club" that Cannon's firing showed "what you can do when you have the power. And if there's one thing Jewish people have showed us, it's they have the power."

"That's me having a cultural blind spot and being culturally clueless to the Jewish culture and not knowing that that was considered an insult," he told me. "But when I sat down and I talked to people around me that are of the Jewish faith, Jewish culture, they explained it to me."

When he made the comments, he said, he had been frustrated that Black people didn't have the collective power to bring criminal charges in three police-involved killings, including that of Breonna Taylor.

"But Nick said something deemed antisemitic, or was antisemitic, and he was out of there," he said. "So for me, it was just like, yo, I want that same type of respect for the Black community. I don't want people to be able to do things to people in our community like kill us and there not be consequences and repercussions for it."

Out of the fire and into the mainstream

In between our conversations, Charlamagne announced another new project: the Mental Wealth Alliance, a foundation focused on providing mental-health resources for Black Americans.

Since he has so many projects in motion, I asked him whether he was concerned about balancing the raw persona that has shaped his career with the restrictions and responsibilities of mainstream America.

"No," he responded. "Because what is mainstream?"

"Nowadays the mainstream is Black. Mainstream is hip-hop. And it's been like that for the longest. If you look at the pop stations, pop stations aren't doing great. And the reason pop stations aren't doing great is because pop radio stations haven't embraced the fact that pop music is Black music ... Lil Baby sold more records last year than Taylor fucking Swift!"

While Charlamagne's rise has largely followed Stern's "shock-jock" blueprint, it has also coincided with hip-hop's shift to the mainstream. But now that most of his business endeavors have moved away from music, I asked him whether he still considered himself a hip-hop figure who held influence over the genre.

"Hell yeah, I'm always going to be hip hop. One thing that people fail to realize when it comes to hip-hop is that hip-hop has always been broad. Long before there was a Black Lives Matter movement, NWA was screaming fuck the police," he said.

"It's so weird to me how people still wanna cater to what they call the mainstream. It's even so weird to me what people even call mainstream. Like, nah, man, I'm happy doing what I do."

A few weeks later, a clip from Charlamagne's "Donkey of the Day'' segment from "The Breakfast Club" made the rounds online. In the video, Charlamagne gave himself the infamous title, which has been handed to everyone from Tyrese Gibson to Nancy Pelosi and is signaled by an animated, braying hee-haw.

He issued an apology to the former NBA player Kwame Brown for discussing on the air intimate parts of his family history, including his father's and brother's convictions for murder.

This wasn't the first time that Charlamagne had given himself the "Donkey of the Day" title or apologized on the radio, but there was something different about this moment. In the past, similar concessions had been preceded by backlash: In 2018, it was his association with a Trump-supporting Kanye West that earned him a hee-haw.

But there hadn't been any notable mainstream controversy surrounding his initial comments about Brown. In fact, during the episode, he attempted to defend Brown against internet trolls before he inadvertently made light of his violent family history.

At the end of his apology, Charlamagne told listeners that he has never claimed to be perfect; that he would make mistakes because "the same things people listen to me for are the same things they hate me for: Because I talk too much. I overshare. I overshare about myself, I overshare about others, and that has historically got me into trouble."

"Some things," he said, "just don't need to be said on the radio."