Neal Brennan co-created one of the greatest sketch series of all time. Now, a decade and a half after the acrimonious end to 'Chappelle's Show,' the go-to guru to Chris Rock, Amy Schumer, Seth Meyers and more is emerging as a major force in his own right.

"Let's talk about white privilege."

Outside, winter's bite is lingering well into March; but here, on The Comedy Cellar stage, Neal Brennan's just warming up. He moves between a microphone and a nearby notepad, his sartorial choice — a hoodie and hipster glasses — belying his 45 years of age.

"Right, Wil?" he calls out to the night's emcee, a youngish black guy.

"Finally," Wil responds, game for the comic volley.

"Sure, Wil, as a black person, you're like, 'What do the whites think of this?' "

Wil's trying to hold it together.

"I've just started calling it out," says Brennan. "Like, internships, that's some white people shit."

Wil's losing it now. So is the audience.

"They're like, 'Yeah, you're going to work for free, for as long as I want you to.' Black people hear that and are like, 'Hmm, sounds familiar.' "

Brennan keeps going, at ease with the potentially fraught subject matter and very much at home onstage. It's been more than a decade since Chappelle's Show, which he co-created with its namesake, ran off the rails, and though he's never lacked for work — quietly establishing himself as a go-to comedy guru to some of the biggest players in the business — it's taken him that long to build his own name to the point where audiences turn out to see him. Now, for the first time in his professional career, Brennan is introduced as more than simply "the man behind the best black sketch series in history."

He credits his one-man show, 3 Mics, which Netflix turned into a widely lauded special in 2017, with giving him an independent identity in the industry — and for helping him get over the intense hurt he felt over how Chappelle's Show ended. For years, Brennan had reservations about getting up onstage, fearing the throngs of hecklers who would shout, "Where's Dave?" if ever he did. "No one wants to see the writer," he had convinced himself. "It's like, 'You guys like Skittles? Cool, the guy who made up the recipe is here. No, he doesn't actually have any Skittles …' " But the naysayers never surfaced, and Brennan kept chipping away at his own act.

The comic community was considerably quicker to embrace him. In fact, since Chappelle's Show wrapped in the mid-aughts, Brennan's helped so many well-known comedians it's become a running joke with his celebrity friends. Ali Wong is among those who now tell him he can stop "helping famous people" since he's already cemented his status as the industry's ultimate comic whisperer.

When Dave Chappelle and Aziz Ansari were tapped to host Saturday Night Live last year, both brought in Brennan as a writer for the week. When Seth Meyers was crafting his famed set for the 2011 White House Correspondents' Dinner, he handpicked Brennan for his writing team. SNL's Michael Che regularly gut-checks jokes with him on Saturday mornings, and Chris Rock has had him punch up more than one script. When it comes to specials, everyone from Hasan Minhaj and John Mulaney to Amy Schumer and Michelle Wolf has enlisted Brennan's help.

"Neal never tries to force his style onto you; he tries to help you find your style," says Meyers, who also praises Brennan's encyclopedic knowledge of comedy and his candor in assessing it. Rock echoes those comments, adding: "The same way everyone bobs their head when they're in the studio with their musician friend, the same thing happens to famous comedians, and before you know it you suck. Neal not only won't laugh, he'll tell you who did a much better version of the joke you thought you just wrote."

Compensation for Brennan's side hustle can come in many forms, from elaborate gifts to a simple IOU. When he assisted Ellen DeGeneres on her recent Netflix hour, Relatable, Brennan got both a consulting producer credit and a rose gold Rolex with the word "Relatable" inscribed on the back. ("Rich people jokes," he teases, lifting up the five-figure watch on his left wrist.) For helping Rock on his 2018 special Tamborine, he collected a paycheck, an EP title and a "thank you" three-wheel motorcycle, which Brennan sent back with the delivery guy — but not before posting a shot of the "death machine" on social media.

Spending time in Brennan's company can occasionally feel like an almost absurdist exercise in Hollywood name-dropping, though somehow it never feels forced. The first time we meet, over Impossible burgers in his Venice, California, neighborhood, he's just flown back from the East Coast, where the never married comic hung with Chappelle, lunched with Jerry Seinfeld and caught up with Jon Stewart at a Knicks game. Says Meyers, who recently tapped Brennan to direct his forthcoming special: "It's like you think Neal's this diamond in the rough that you discovered; and then you realize, nope, he's just a diamond."

***

Brennan was doling out advice long before anyone considered it wisdom. As the youngest of 10 in his chaotic Irish-Catholic, suburban Philadelphia home, he'd chime in with opinions just to get a word in. "I was the baby," he says, "dying to be heard."

By the time he turned 18, Brennan had decamped to Manhattan, where he dabbled for half a year at NYU Film School before landing a gig as the door guy at a downtown comedy club. When he wasn't collecting tickets, he'd pitch tags and punch lines to the night's comedians, most of whom were probably baffled by his chutzpah.

When Chappelle dropped in, it was different. The two were roughly the same age, and one of the first lines Brennan lobbed his way landed. Soon, they were workshopping others, including an early Chappelle bit about the origin of the N-word. By the time Chappelle shot Robin Hood: Men in Tights the pair had grown so close that Brennan would tag along as Chappelle dined with Mel Brooks or stopped in at Arsenio. There was no formal role for Brennan: "Just his buddy," he says, "and maybe the most successful hanger-on of all time."

Brennan used that period to soak up everything he could about show business. In time, he picked up work, too, writing on series like All That and the dating game show Singled Out. ("You're welcome," he jokes.) Then came a call from Chappelle. He'd told a few people he and Brennan had a stoner comedy up their sleeve, and now he had to produce one. Within a month, the pair cooked up Half Baked for Universal.

Things went south quickly. The young, inexperienced duo had no sense for what to push back on or what to let go. By the time they saw an early cut, at least one of them was in tears. "I think it was Dave," Brennan says. The money proved dismal, too, with Brennan making more off residuals than he did on the film itself. Half Baked landed in 1998 without much fanfare, grossing just $17 million — though in the years since, it's achieved a kind of cult status.

Before any of that, Brennan's place within Hollywood's hierarchy had already changed, a fate Chappelle had tried to prepare him for. "Congratulations," he'd said when the Half Baked deal closed, "you're officially a witch doctor." Having already had his share of success, Chappelle explained that people would start ascribing wisdom to Brennan simply by virtue of him having sold a studio project. Brennan still marvels at how quickly it happened, remembering how people were suddenly interested in his take on material: "I could just feel this sense of import on what I thought."

***

Brennan's import would grow exponentially once he and Chappelle reunited to pitch a sketch series loosely inspired by the Hugh Hefner variety show Playboy After Dark. Their first stop: HBO, where Chappelle had made a popular special. "But they looked at us with such contempt," says Brennan. "They literally said, 'We have Chris Rock, why do we need you?' "

So, the pair trudged up Sixth Avenue and sold Chappelle's Show to Comedy Central.

There'd be kinks to work out, but by season two in 2004, Chappelle's Show was a full-blown phenomenon — not only a giant hit for Comedy Central but, with 9 million units sold, the top-selling TV DVDs of all time. The New Yorker called its star "the most prominent, racially astute social critic we have," while New York magazine praised the series for pushing "the boundaries of what was permissible on TV."

"People always ask, 'Did you guys set out to make a multicultural [juggernaut]?' " Brennan says. "No, we were just two angry guys who set out to make one of them famous. I mean, it's so dumb to say, but most of the impetus for the series was showing people that Dave is as talented as Chris."

Brennan's status in the industry rocketed, too. Overnight, there was no velvet rope he couldn't breeze past, and everyone seemed to have a script or want a meeting. Then came time for season three, and one of the more contentious renegotiations in TV history. Brennan recounts with agony how Comedy Central pitted him against his best friend. In the end, the network backed up the Brink's truck for Chappelle — a $50 million, two-season deal — leaving Brennan with "a lunch box of money."

What Comedy Central hadn't fully considered, he says now, was that the two would have to continue working together. "Once I'd seen how easily disposable I was and how easily manipulated [Dave] was into disposing of me, it was really painful," Brennan adds. "And then people were going, 'Watch Neal,' and all this shit. And it was like, watch Neal do what? Write and direct sketches? Like, what are you watching me for? What am I going to do? I wanted to do it with him. I liked him."

With the gulf between them widening, the two men went back to work. They wrote a slew of sketches and shot several of them. But as the show's third-season premiere drew closer, Chappelle was finding the spotlight increasingly unbearable. "It was toxic under that microscope," says Brennan, defensive of his pal. "It's like he'd become the black spokesperson." Then, in April 2005, Chappelle abruptly fled to Africa.

The media began floating theories about his disappearance: He'd cracked up, he was on drugs, he was locked away in a mental institution. Eventually, he appeared on Oprah to reveal, among other things, how some of the sketches had begun to feel "socially irresponsible." Chappelle cited one, in particular, in which a pixie in blackface appeared as the visual personification of the N-word. He explained how he'd heard one of the show's white employees laughing at it in a way that made him uncomfortable. Without getting specific, Chappelle told Winfrey: "I know the difference between people laughing with me and people laughing at me."

The trouble for Brennan was that he was the only white person affiliated with the show whom people knew anything about, so the natural assumption was that it must have been him. "There was this suspicion that I felt for years," says Brennan. "White people thought I was cocky, and black people thought I was racist, and it's like, 'No, I'm clinically depressed and have some very funny observations about black people that are not founded in racism — they're founded in just fucking funny.' "

It should be said that the industry's biggest black stars never turned their back on Brennan, including Rock, who refers to him affectionately as "Neal Brennan, friend of the black man," because, he says, "he's one of the few white comics who views all comedians equally."

Still, it would be years before Brennan and Chappelle — who eschews nearly all press opportunities, including this one — rekindled their friendship; and to this day, Chappelle's never publicly exonerated his buddy. At first, Brennan tried to distract himself, making his directorial debut with the 2009 bomb The Goods, starring Jeremy Piven as a used-car salesman. But he remained crushed and uninspired. "It's still the most painful thing that's ever happened to me," he says, holding back tears. "The guy meant the world to me and the show meant the world to me, and then, within a couple months, it was all gone."

***

If his experience on Chappelle taught Brennan anything, it's that he'd had enough of being the guy behind the guy. It was time to be the guy.

The solo path was a slog at first. His Chappelle credit opened plenty of doors, but it failed to put butts in seats. Even Comedy Central would only agree initially to give him a half-hour special. After it performed, Brennan got his own hour. "You'd think they'd go, 'Well, there's $100 million he's made for us that we know of, so maybe give him the benefit of the doubt?' " he says. "But whatever the inverse of the benefit of the doubt is, people gave me that."

Brennan spent the better part of the next decade trying to disabuse people of their preconceived notions about him — and, at the same time, prove that he had the chops to make it on his own. "People just don't know," he says. "They go, 'Well, one of you had to have done all of it and we're gonna bet it was Dave.' " In truth, the pair wrote every Chappelle sketch together, passing a laptop back and forth for hours at a time.

Then came Brennan's one-man show, 3 Mics, which premiered in early 2016 at Manhattan's off-Broadway Lynn Redgrave Theater. The New York Times review compared the experience to "eavesdropping on someone's therapy sessions," with Brennan moving between microphones: one, to unleash a collection of one-liners; another, to deliver a polished stand-up set; and a third, to get unflinchingly candid about his own life, revealing a tortured relationship with his late father, a violent alcoholic, and his struggles with depression, including a battery of intense treatment options that failed to provide relief.

"Depression feels like you're wearing a weighted vest," he offered from stage. "And the medication could take some of the weights out of the vest, but I still came across to people as bored or cold or superior, none of which I wanted to come across as." Sensing his own bleakness, he pivoted: "But you know who always loved my attitude? Black dudes. Always. They'd be like, 'Neal, man, you don't give a fuuuuck.' And I always wanted to say, 'Well, that's because I'm sad.' "

Brennan's pal Trevor Noah is not alone in calling his act "raw and visceral," adding, "And it's not a bit — it's who he is." Brennan's siblings, caught off-guard by his decision to air intimate details about their family, weren't as uniformly positive; one sister confronted him after seeing the show. "She was like, 'Did you ever think maybe I didn't want all that stuff out in public?' " recalls Brennan. "And I hadn't. It's just as much my story as anyone's."

It didn't take long for Netflix to turn 3 Mics into a special. "It was this entirely original, captivating work," says Netflix's stand-up exec, Robbie Praw, who keeps a 3 Mics poster hanging in his office and has already commissioned another hour. "And we knew it deserved a big platform."

More doors swung open. The streaming service featured him on its Comedians of the World stand-up series earlier this year. The Daily Show, where he'd been a writer and adviser, upped him to on-air correspondent. And comedy bigwigs like DeGeneres and Seinfeld began paying attention. "It feels like I'm in a club that I wasn't in before," Brennan says, before rattling off a series of forthcoming projects, including more commercials (he's made "insane money" directing spots for Nike and Sprite) and a potential show with Breakfast Club host Charlamagne tha God.

The volume of incoming calls for advice has grown exponentially, too. For all his individual success, Brennan still finds plenty of rewards in the collaborative experience. "I'm going to watch [whatever these people do] anyway," he says, "and my brain's going to come up with things, so I might as well share them." When it came to Rock's last special, much of Brennan's input was performance-based. As the comedian mined his divorce and custody battle, Brennan suggested he sit down: "I was like, 'You can't Chris Rock it, you can't pace, you have to sit there and be a person.' " Schumer called Brennan the night before she filmed her new hour, Growing, to bounce jokes back and forth. "Seventy percent of what Neal pitched went in," she says. "He just knows what's funny."

Back at the Comedy Cellar, Brennan is focused on his own act, readying his second set of the night. Before long, he's back on the subject of white privilege; this time, by way of his own atheism. "I don't like saying I'm an atheist because atheists are such smug dickheads," he says, "and I say that as a vegan, so I know smug dickheads." He's got the room's attention now.

"It's funny, I know a lot of white atheists, but I don't know a lot of black ones, and I got a theory about why: Because atheism is really the height of white privilege." The bit's landing well, and Brennan knows it. "Think about it: Religion basically says, 'Hey, can we interest you in an after-life?' And white people are all like, 'No, thank you.' Like, 'Why, how much better can it be?' " The crowd is howling now, and Brennan stands there, all by himself on New York's most iconic comedy stage, taking it in.

This story first appeared in the April 11 issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.