It didn’t help that the rapper had been getting fewer than five hours of sleep a night lately, thanks to a grueling schedule. In addition to finishing the album, Bun B had launched a blog, co-authored a book, and spent an inordinate amount of time promoting the three—all while finishing up a semester as a distinguished guest lecturer at Rice University. At age forty, he was one of the hardest-working performers in the music business, with a remarkable longevity in the youthful universe of rap; that same month marked the twenty-first anniversary of the first album released by UGK, short for Underground Kingz, the group he’d formed with the late rapper Pimp C. The pair had helped introduce Texas rap to the world, an accomplishment that had since earned Bun B the honorific “original gangsta,” or OG.

That he had rapped in front of crowds 25 times the size of this sold-out audience in Jones Hall didn’t seem relevant. As the moan of a violin warming up drifted in from the stage, Bun B’s official photographer, his videographer, his social media promoter, his manager, and a Houston Press photographer watched him attentively, documenting every move with their cameras. Bun B struggled several minutes to tighten the tie band around his tuxedo collar, then cocked his right eyebrow. “This tie isn’t working,” he said. “This tie is not going to work.” His crew exchanged glances. He was nervous.

As Bun B stood before a mirror in a fluorescent-lit room the size of a walk-in closet, tugging on a dark-purple bow tie, his entourage huddled by the door, assessing his mood. Just a few hours earlier, the Grammy-nominated rapper—the famous surviving half of the hip-hop duo UGK—had seemed buoyant, with a nod and easy smile for anyone who approached. He had recently released his fourth solo album, Trill OG: The Epilogue, and he would soon be heading out on tour. But now, minutes before the show on this cool November evening, he’d grown solemn, tense. Bun B was about to do something new: perform with the Houston Symphony.

In an effort to calm him, or maybe just break an awkward silence, the videographer, a sweet-natured film school graduate named Sama’an Ashrawi, zoomed in with his camera and asked, “So what’s about to go down?” Earlier that day, Bun B had offered some thoughts on what he felt was at stake. “If this collaboration goes well with the Houston Symphony, just think of the possibilities for hip-hop in classical ballets, classical operas, and so forth,” he said. “There’s room for a lot of groundbreaking interpretation. It makes me want to take something like The Merchant of Venice or Fiddler on the Roof and see if there is a place—one or two places—to incorporate different elements.

“If I do right by this opportunity,” he continued, “it could open the way for many other young rappers to be part of something positive. I only get one shot. I haven’t done it yet. I get one time.”

Ashrawi, who had banked hundreds of hours of Bun B footage at family barbecues and other events, had been witness to this kind of creative fusion before. Bun B’s vast network of contacts and eclectic array of tastes—the blog he’d just launched, with sneaker site founder Premium Pete, was all about food; the title he’d just published, in collaboration with middle-school science teacher Shea Serrano, was Bun B’s Rap Coloring and Activity Book—were in part what made his fans, some 900,000 of them on Twitter, so devoted to him. Bun B didn’t just habitually cross genres and media platforms, he also moved among Houston’s subcultures with a native’s easy authority. He seemed to embody modern Houston itself, his endeavors a celebration of the steamy, glorious complexity of the most diverse city in Texas. This, not surprisingly, inspired a fervent sea of followers, Ashrawi among them.

Except that, at this moment, Bun B wasn’t feeling quite so self-possessed. “If you want to video me, you can video me, but we’re not going to do a Q&A and all that; this is nerve-wracking enough as it is,” he snapped. Unfazed, Ashrawi turned to me instead and began describing his love for Bun B, summarizing his feelings with “How does the grass thank the sun?”

A petite blond woman in her sixties poked her head in the doorway. “You guys doing okay?” she asked, as Bun B pulled off his tie and traded it for another. “You look beautiful. I’m so proud of y’all.” Her name was Sherry Levy, she said, and she was a volunteer for the Anti-Defamation League, which was co-hosting the concert with the Houston Symphony in honor of the two organizations’ centennial anniversaries.

It was Levy who was responsible for Bun B’s being there. After hearing that one ADL member had purchased concert tickets for 650 high school students, Levy had turned to her daughter, Gillian, for suggestions on a musician to include who would appeal to the teens. A college senior, Gillian had resented growing up in the “conservative bubble” of Houston, as she called it—until she discovered the vibrant local hip-hop scene. This changed her view of the city, and of herself. (“I realized how great our rap scene is, and it made me proud to be from Houston,” she told me.) The person at the center of that scene, she told her mom, was Bun B.

Curious ADL board members who Googled “Bun B rapper Houston” would have unearthed a peculiar combination of images. Some photos show a large glowering man in an assertive pose, wearing a baseball cap and an imposing gold chain, promoting song titles such as “Murder” and “That’s Gangsta.” But there are also photos, taken in recent years, of him in a staid V-neck sweater, his beard shaved close, smiling like a toothpaste model. Those doing the research might have gathered that Bun B is a big deal—he has collaborated with Jay-Z and OutKast, among others, and Beyoncé counts him as a friend—but they might not have fully understood his role in defining Houston for young people across the globe. In other words, these symphonygoers still weren’t sure exactly what to expect. And now they were in the audience, waiting.

At eight o’clock, the lights dimmed, and the audience’s murmurs quieted as heroic trumpets and thundering timpani signaled the start of “Fanfare for the Common Man.” Backstage, everyone cleared out with the exception of Bun B and his acolytes, who tried to look anywhere but his direction: the floor, a watch, a phone. Bun B straightened his lapels repeatedly, peering out the small window of a stage door at the orchestra. He started to pace. “This is my life now,” he said.

Bun B’s life these days is so deeply intertwined with Houston’s that he is often referred to as the city’s unofficial mayor. He has been featured in anti-texting public service announcements. He helps publicize drives for the Houston Food Bank. He hosts a twice-weekly segment on the TV station CW39 called Bun’s Beat (recent installments include “Bun B’s Thoughts on the NFL Banning the N-Word” and “Bun B’s Advice for Returning College Students”). He has been a regular guest on networks such as Comcast SportsNet Houston to discuss the Astros and the Rockets. He attends nearly every major concert. He promotes the city’s food and culture actively on his Twitter feed, where he can seem, at times, like a one-man chamber of commerce. “If you want to find out the best sushi spot, barbershop, or club, he would probably be the person with the widest Rolodex,” Houston rapper Chamillionaire told me. “You could ask him something crazy, like where to find left-handed scissors in Houston, and he could probably point you in three different directions.”

Houston’s actual mayor, Annise Parker, doesn’t claim to be so hip as to know all of Bun B’s music, and she finds some of his lyrics “out there,” but her respect is obvious. In 2011 she proclaimed an official “Bun B Day” in honor of his charity work, and the two are so friendly that during the Rockets playoffs last season, Bun B texted to invite her to watch from a suite. She hesitated at first—she doesn’t like socializing during games and worried she might stick out too much among a bunch of rappers—but eventually agreed. “And it was the damnedest thing,” she told me. “It was like being in a suite full of sports fans who are all introverts.” On Twitter, Bun B has called Parker “Best. Mayor. Ever.” She has reciprocated by touting his coloring book with the hashtag #keephoustontrill.

Kalele Thumbutu

“Trill,” the mayor understands, is a word closely associated with Bun B. Consider the titles of his previous solo albums: Trill, II Trill, and Trill OG. The tour he kicked off in March to promote the last installment in that series is called “The Trillest Tour.” The lyrics on his solo and UGK releases contain the word “trill” more than 250 times, as in, “No matter the situation, we gotta keep it trill.” The word, which he has trademarked, was a term that originated in the penitentiary and was spread by ex-prisoners in Port Arthur, where he grew up. It has appeared embroidered on his baseball caps and emblazoned on his T-shirts. He is asked for a definition so regularly that sometimes his voice betrays just a hint of exasperation. “Being trill really just means being true to who you are,” he told NPR the week of his symphony appearance. “ ‘Trill’ does not mean keeping it hood, does not mean keeping it gangster, or anything like that.”

This firm sense of identity is what makes Bun B such a compelling statesman. He is a devoted family man, with a wife of eleven years, two grown stepchildren he raised as his own, and a school-age granddaughter, who lives with him and his wife and fills much of his Instagram feed. And he inhabits a vaunted role as a mentor in the hip-hop community, where he has an unmistakable imprint. New artists mention him in their work (“Shout out to Bun for the opportunity,” wrote Houston rapper Propain in his song “Move On”), and he is regularly invited to perform on songs and in videos with locals like Lil’ Keke and Mike Jones. He goes to so many concerts that fledgling artists consider his attendance a validation of their work, as Drake admitted in the song “Too Much” when he rapped, “Backstage at Warehouse in ’09, like, ‘Is Bun coming?’ ”

A consummate OG, he is generous with his advice. With musicians he doesn’t know well, his encouragement can take the form of a compliment, as it did on the online Combat Jack Show in 2012, when he turned his attention to his fellow guest, a young rapper from Indiana named Freddie Gibbs. “You familiar with [the rapper] Threat, Freddie? Sickinnahead?” Bun asked. “When I look at the way he draws and paints his pictures, you remind me of that.” He went on, “It’s that third-person narrative—you know what I’m saying?—that some people can only do so well.” With those he knows better, he says, his instruction can be a little more raw: “I’ll say something like ‘Hey man, you may get this now, but two months from now, you’re gonna end up like that and you’ll feel like shit that you fucked with your life. So don’t do that. I did that. It bit me in the ass, and you’re about to do it bigger than I did and it’s going to come back and bite you harder.”

Artists like 24-year-old Kirko Bangz and 33-year-old Slim Thug, who have been the beneficiaries of his counsel, are grateful. “Most of the time I talk to him, it’s about real-life stuff,” said Bangz. “Like how to act. You gotta have your wits together in this game. You gotta understand that when you’re out there, you belong to the people.” Slim Thug, who has been friends with Bun B for more than a decade, heard similar warnings in his youth. “I ain’t gonna lie, I was just wild,” he said. “Back then, I had the attitude of ‘I’m from the hood, and before I had anything, nobody gave a damn about me, so I’m gonna live my life how I want to live it and do what I want to do.’ And that’s when he just took me by my shirt and said, ‘Hey man, chill out about all this.’ ” I asked if Bun B still gave him advice. “To this day!”

Though Bun B is similarly generous with his fans—he encourages those who share links to their music; he takes to Twitter to note birthdays, anniversaries, and sympathies; he poses for photos—his influence might not have been fully appreciated outside the world of rap had he not, in 2010, been invited by Anthony Pinn, a religious studies professor at Rice University, to speak in front of a class about the moral codes in hip-hop. It turned out that Bun B, who for the past ten years has attended the Church at Bethel’s Family, on the southwest side of Houston, had already pondered the topic. “He was very thoughtful, very clever, very compelling,” remembered Pinn, and it occurred to the professor that “there was every reason to bring him on in a more sustained way.” In January 2011 “Professor Trill” began co-teaching a course with Pinn titled “Religion and Hip-Hop Culture,” a class so intriguing that on the first day the auditorium was filled to capacity with curious students.

The class raised Bun B’s profile across the city, and the collaboration seemed to inspire even more creative civic pairings: this past summer, for example, the Blaffer Art Museum hired Bun B and Uchi chef Philip Speer for a VIP culinary event with live music (during one course, Speer doled out a pork belly bun with pickles and herbs while Bun B rapped his self-titled song “Bun”). An ambassador of sorts, he brings the rap community’s conversations to a wider arena—as when he appeared on MSNBC to discuss the admissibility of rap lyrics in criminal trials—and is always quick to examine hip-hop culture itself. At a public panel he led in 2011 on the topic “Should Rap Be in Church?” he didn’t shy from pointed questions about his lyrics. “First of all, let it be said that I do not create my music for children,” he began, standing behind a lectern in a cream-colored sweater vest. He considered many UGK songs to be morality tales, he said. Yet he also remembered feeling queasy the day his daughter walked into the house singing a rap song he considered inappropriate for her age. “That was not a good moment for me,” he acknowledged. “I’m a grandfather now. So I have to wonder if everything I said is stronger than what I did.”

This was typical Bun B: calm, introspective, diplomatic. “One thing I’ll say about him,” said Lil’ Randy, a deejay for the Houston rap group the Screwed Up Click, “is he would keep his calm in a sticky situation.” There is intention behind this composure. “The reason I’m very calm,” Bun B told a Combat Jack Show interviewer last May, “is because when I turn it on, I don’t know how to turn it off.”

“When was the last time you were really pissed off?” the interviewer asked.

“A couple of months ago,” Bun replied. “This kid got killed in Port Arthur, Texas, and my wife and I were really upset and concerned.” His wife, he explained, posted something about it on Instagram, which some followers misinterpreted as an insult to the town, and one user had suggested that someone punch her. Bun, with chagrin, recounted how he’d gone to the Sonic Drive-In where he believed the culprit worked, only to discover that the man was not employed there.

“My plan was not just to beat him up but to beat him up at his job and embarrass him at his workplace and make him lose his job,” he said. “I look back on it in retrospect, and it probably wouldn’t have been the best thing for me to do, because there was a Stop the Violence rally, like, happening the next week.” His interviewer, unable to contain himself, laughed. Bun B did not.

“That would have been, like, the worst thing I could have done for myself,” he said. “It would have really fucked up my public image with people, because I’m so concerned about community shit.”

Photograph by Jeff Wilson

This is not language, his mother says, he learned from her. Ester Taylor likes to be clear about that. She is a churchgoer; she doesn’t drink or cuss, and her principal vice is bingo. A tranquil, round-faced woman with a gentle smile, she still seems to be adjusting to the fact that her son is in the music business. She never imagined that one day he would buy her central air-conditioning, not to mention Louis Vuitton purses or other luxuries she usually refuses to accept—or that her neighbors would continually ask about him. “I went to the grocery store one time,” she said, “and this little white guy ran up after me: ‘Excuse me! Is this for real, you’re Bun B’s mother?’ ”

A native of Louisiana, Taylor moved to Texas as a newlywed when her husband, Rodney Freeman, got a job with the railroad in Houston. The couple had four boys, the last of whom acquired the nickname Bunny—further abbreviated Bun—as a way of shortening his given name: Bernard. When the marriage eventually dissolved, Taylor yearned for life in a small town, and in 1984 she and her two youngest sons moved to Port Arthur.

An oil boomtown in the twenties, Port Arthur hit economic troubles in the sixties and steadily declined thereafter. By the eighties, layoffs at the refineries and the influx of crack cocaine had aggravated this reality. Though Taylor, who remarried, provided her children with a tidy house in a decent neighborhood, with a carport and trim bushes out front, she could not shield them from the town’s gritty side. Port Arthur rapper Hezeleo, who grew up with the young Bernard Freeman, recalls one notorious section, a two-block segment at the end of Texas Avenue that locals called “Short Texas.” “It was like a strip in Vegas,” he said. “As I got to being more aware, I realized that we were in the hood, and the hood would come alive at you at any moment, so you had to be prepared to carry yourself a certain way.”

Taylor wasn’t overly strict, but she insisted on good manners—no cussing—and demanded that her son iron his pants before going to school. “I wanted him to teach,” she said. He was smart and got good grades; she imagined he might become a professor. Freeman also had a broad range of interests: he performed in plays, like A Raisin in the Sun, and took debate, where his teacher instructed him not to talk fast, as it detracted from his strong voice. Though he was a force in the classroom—“He could walk up to any circle and chill and kick it and be accepted,” Hezeleo remembered—he nevertheless felt odd. He didn’t know of many other black kids, for example, who dug David Letterman and Rich Little.

Noting the hefty salaries that engineers made at the refineries, Freeman figured he’d go to college and join their ranks—or maybe become an actor or a teacher, as his mom wanted. He could not have imagined then that music, in which he had an insatiable interest, would take him anywhere. But he feverishly gathered new cassettes and mix tapes of the latest rap acts whenever he visited his dad in Houston, and he impressed his friends with his ability to memorize lyrics. (Jelon Jackson, a high school friend, said, “He’d listen to Run-DMC or something and learn the words the next time around.”) The summer after tenth grade, when a few of his peers began to compose original raps, Freeman decided to try his hand at it, and soon he was writing more than anyone he knew, often modeling his work on that of rapper KRS-One, whose socially conscious ideals he admired. He wrote at least ten pages a day, honing his skills. (“I remember we would go to lost-and-found and get notebooks,” Jackson said. “People would trash them and he would pick them up and use them to write rhymes.”)

It was around this time that Freeman met Chad Butler, a teenager at a rival high school, whose passion for rap matched his own. “[Butler] was a nerdy guy, like myself, who loved music,” said DJ DMD, one of the innovators of the Port Arthur hip-hop scene, who met Butler as a ninth-grade trumpet player. Like Freeman, Butler scoured music stores and looked forward to trips out of town, like the intramural choir competition in Austin, so that he could load up on cassettes. “We would try to buy things we knew nobody in Port Arthur would have,” said former chorus mate Mitchell Queen, “so that when we traded, the trade was worth something.”

Perhaps because they were so similar, Freeman and Butler did not like each other at first. Freeman’s trips to Houston gave him stories about seeing famous rappers in clubs, and one night at a football game, after he had been crowing about having seen the rapper Eazy-E, Butler could no longer hide his annoyance. “Nigga, stop lying,” he said. “You lying all the time. You know that’s a goddamn lie. You don’t know that nigga.” Freeman pulled out a photo as evidence. “Yeah, I do,” he said. Impressed, Butler mentioned that he had some recording equipment at his house.

From that day on, Freeman didn’t consider Butler a friend as much as a brother. Freeman’s relationship with his biological brothers, a couple of whom were incarcerated, was strained; Butler, who was nine months younger than Freeman, was an only child. Freeman, who knew that his mother had lost a baby in childbirth after him, had always craved having a younger brother, and in Butler he found him.

Butler invited Freeman over to his house, and soon the two joined with friends Jackson and Queen to form a group named the Four Black Ministers. After they made a demo tape with four or five songs, which they sold throughout the area, the group changed their name to the Underground Kingz. But the members’ levels of dedication varied, and as graduation approached and college scholarships or commitments began to beckon, the quartet winnowed down to just Freeman and Butler.

By the spring of 1991, Freeman himself had received two scholarships and was entertaining the idea of college. But he felt strangely bound to Butler, who had dropped out of school and, in contrast to Freeman’s own vague ideas for his future, was committed to the single dream of making a record. When Butler secured a deal with a 23-year-old Houston flea market booth operator named Russell Washington, late in Freeman’s senior year, Freeman knew what he wanted to do. He decided to forgo college and concentrate on music.

Ester Taylor couldn’t believe her ears. A rapper’s life was the last thing she wanted for her son. Having already suffered the pain of two sons in prison, she could not bear the thought of another casualty; heartbroken, she gave Freeman a week to leave the house. On graduation day, his one brother who wasn’t in jail came from Houston to attend the ceremony. That night, Freeman told him, “I’m going with you,” and left for Houston.

At the time Freeman moved, Houston was just recovering from the oil bust, and while there were signs of a promising economic future—the Galleria, for example, was beginning to recapture its lost glamour—the city was crippled by the new crack epidemic and a soaring rate of violent crime. It was against this backdrop that Houston’s rap scene had started to form. The only label of consequence was Rap-a-Lot Records, run by a savvy and tenacious businessman named James Prince, who defied the stereotypes of Texas music by promoting groups like the Geto Boys, whose raw lyrics provoked controversy and whose album art included a real photo of one member just after his eye had been shot out. Artists who weren’t on Rap-a-Lot sold their music out of their car trunks or, as the not-yet-famous DJ Screw did, out of their houses. There were three radio stations that had begun airing hip-hop, but hardly any of the music was local. “Houston didn’t have an identity yet,” said longtime radio deejay Mean Green. “Everyone was kinda confused. They weren’t representing Houston. It was all Chicago outfits or Lakers.”

“A monopoly had been established in Houston,” explained Prince. “Every deejay was from the East Coast. At the time, they played nothing but East Coast music. We were considered country and laughed at, as if our raps wouldn’t qualify. We weren’t hip enough to be accepted by them.”

The demo tape that Russell Washington received from Butler and Freeman—who now adopted the names Pimp C and Bun B—featured two young men who were unmistakably Southern, if not distinctively Texan. The first single, “Tell Me Something Good,” which used a sample from the Rufus and Chaka Khan hit of the same title, humped along at a slow, grooving tempo. Rather than hide their drawl, the pair emphasized it—especially Pimp C, who dragged out his vowels as if he were pulling on a praline. When the song won a Houston radio contest, it became a local hit. “I remember when me and Bun heard the song on the radio,” said Washington, “we were in the car, and we started beating on the roof.”

The seven-song Southern Way EP came out in the spring of 1992 on Washington’s Big Tyme Records label, establishing UGK as an unapologetic voice for Southern rap. Amid all the East Coast hip-hop, the title itself made a statement, and Pimp C brought a new dimension to the music by layering live guitars, drums, and bass over UGK’s samples, which were based not on the funk and jazz used elsewhere in the country but on a more soulful sound—the Isley Brothers, Curtis Mayfield. The songs were novel enough to catch the attention of Jeffrey Sledge, then the vice president of A&R for New York’s Jive Records. “The production was very cutting-edge,” Sledge said. “And they weren’t talking about the regular old kind of stuff; they brought you into their world of Port Arthur, Texas.”

UGK’s celebration of their roots did not go unnoticed in Houston and Port Arthur either. “It was a different swag,” said Prince. “It was our swag. Houston swag.”

“In Texas history, you’re taught that you’re better in Texas,” said Houston rapper Paul Wall. “With pride in our state, from sports teams to actors and entertainers to food, we support our own. UGK was one of the first groups to really carry the torch for the Texas music scene and represent us in the lyrics, with places and names and slang.”

Jive Records offered Washington a buyout deal, which he eventually took, and UGK released their first full-length record, Too Hard to Swallow, on their new label. The group finally had the potential to break into the big time, especially after one of the songs off the record—an eerie, grinding song about selling crack called “Pocket Full of Stones”—made it onto the sound track of the movie Menace II Society.

Yet the relationship with Jive simmered with conflict. Some of the executives at Jive, having no template for a Southern group, worried about how audiences would react to such a dramatically different style, and Pimp C and Bun B perceived their support as tentative. The distrust was made worse when Menace II Society became a success, and UGK felt they’d been stiffed on the payout they deserved for creating a hit.

Despite these tensions, or maybe because of them, Pimp C and Bun B remained fiercely loyal to their audience. They took to local radio to air their grievances with Jive, as if speaking to family. They traveled to little clubs, building exposure one fan at a time. “We did a show in Lake Charles where it was, like, fifteen people in the club, know what I’m saying?” said DJ Byrd, a Port Arthur deejay who frequently toured with UGK in those days. “But they knew the songs on the radio with ‘Tell Me Something Good,’ and we rocked it with fifteen people.”

The duo eschewed the trappings of celebrity even as their ensuing albums, Super Tight (1994) and Riding Dirty (1996), increased their name recognition. Matt Sonzala, an Austin events promoter who traveled from coast to coast, writing city reports for the rap magazine Murder Dog, said that when he asked street rappers for influences, almost 90 percent of the respondents said UGK. “It shocked me,” he told me. “UGK didn’t have videos on MTV; they didn’t have songs on the radio across the country.” When Bun B met Biggie Smalls, around 1994, Bun B complimented the more established artist, “Yo, Biggie, you’re a bad motherfucker,” to which he responded—much to Bun B’s amazement—“I heard your shit too; I know who you are.”

While some of Bun B’s earliest lyrics reflected the crude impulses of a teenager (as in the famously gross “Pregnant Pussy”), now his words frequently revealed his depth of thought and his bottomless lexicon—a perfect foil for Pimp C’s lyrical simplicity. “Even though it was grimy, it wasn’t sloppy,” said Prince. The song “Murder,” for example, is considered by many rappers to be Bun B’s sharpest work:

Playa hater ditch digger figure

My hair trigger give a hot one in yo liver

You shiver shake and quiver

I’m frivolous if a nigga you wetter than a river.

“Bun B’s verse on ‘Murder’ was one of the most lyrically complex rhyming patterns I had ever heard anyone from the South spit,” said Chamillionaire. “I remember rewinding it a lot and listening to it over and over, so I could memorize it. I was amazed at his breath control and how many rhyming words he was able to squeeze into each bar.”

In what may be UGK’s saddest and most powerful song, “One Day,” Bun B rapped about a former classmate who got killed in a dice game and a friend who fell asleep behind the wheel of a car and drowned after driving into a canal. “So shit I walk around with my mind blown in my own fuckin’ zone,” he raps, “ ’cause one day you here but the next day you gone.” At an appearance in Barcelona in 2008, Bun B confessed that he has cried onstage when performing that song. “We’re talking about people that we loved and lost, and that is when music is supposed to be at its best,” he told his audience.

Inevitably, perhaps, his mother’s worries about his career choice were soon substantiated. Bun B once described his young self “smoking fry and drinking E&J and dirt weed and getting into fights and shit.” He told one interviewer that he sold crack cocaine, though he never partook of the drug himself, having seen it destroy too many of his neighbors in Port Arthur. Although he partied alone in those days and says that “nobody knows the full amount of dumb shit I’ve done in my life,” he leaves vivid hints. As he told McSweeney’s magazine in 2006, “I was literally on the highway, with cocaine on the dashboard, car on cruise, with my feet out the window, smoking a blunt, begging a state trooper to take me away for the rest of my fucking life.”

Officers did arrest him for possession of marijuana in 1997, keeping him locked up for three days. Sitting in his cell, Bun B considered how many of his contemporaries were dying, going to prison, or losing their minds from the drugs they were doing. He decided at that moment to “chill out from here on.”

Pimp C, meanwhile, chose differently. He had been charged with marijuana possession back in 1995 and spent a few days in jail; now he dressed flamboyantly, in a mink coat, and walked with a swagger, saying whatever was on his mind, wise or not. “To the young men of the city, he became our superhero,” said Houston Press music photographer Marco Torres. His persona grew even bolder in 1999, when UGK appeared on Jay-Z’s Grammy-nominated song “Big Pimpin’.” “He was extremely volatile at that time,” said Sledge, the former Jive vice president. “Probably the most volatile he ever was.”

His temper got the better of him one day in December 2000. He had walked into a shoe store at a mall and was talking to Bun B on his cellphone when a woman began to loudly insult him. Not one to flee a fight, Pimp C hung up and faced her, offering his own vociferous opinions. The two went toe-to-toe for a minute as her friends watched and laughed, until Pimp C believed he saw the woman reach into her jacket. He lifted his coat and showed a pistol, then asked her to freeze. “Y’all need to back up out of this store, this is not funny no more,” he told them.

Security was called, and when the guards found Pimp C in the parking lot, he was charged with aggravated assault with a deadly weapon. He pleaded no contest and got probation, but when he fell behind on his community service requirements, in 2002, the judge’s patience wore thin. He was sentenced to eight years in prison.

Everyone had an opinion about how Bun B should move forward. He could disband UGK, go solo, or find a new partner. But when a representative at Jive noted a clause in UGK’s contract stating that a member who went to jail or died could be replaced, Bun B’s reaction was clear. “Bun was like, ‘That’s not happening,’ ” said Sledge. “It wasn’t even a discussion.”

That anyone would even dare think he’d abandon Pimp C was proof to Bun B of the lack of loyalty in hip-hop culture. He was appalled; he had never bought into the philosophy of, as he calls it, “Get what you can, do what you can for you, and fuck the next man,” least of all when it came to his inner circle. Instead, to keep UGK’s name alive, he hatched a plan.

It became known as the “Free Pimp C” movement, a public relations crusade to promote his partner against all odds. Bun B appeared on records by Paul Wall, Ludacris, and other big-name hip-hop artists, working the phrase “Free Pimp C” into the raps; soon fans were buying “Free Pimp C” T-shirts at mall kiosks and record stores. It helped that Texas rap, led by artists such as Wall and Mike Jones, was finally dominating the charts; listeners across the country now memorized lyrics about the candy-colored cars and codeine syrup of Houston’s hip-hop culture. (“If you look at the East and West coasts, you see they have grills in their mouths—the very image we created down south,” said Rap-a-Lot’s Prince. “The script has flipped.”) Rappers increasingly requested Bun B’s appearance on their songs, until there came a moment when an artist was basically a nobody if he didn’t have Bun B on a cut, rapping “Free Pimp C.”

Pimp C’s homecoming, in 2005, couldn’t have been timed any better. Two months after Bun B did finally record a solo album, Pimp C was released on good behavior, a bigger folk hero than before he’d gone away. “Next thing you know, he was Bob Dylan,” remembered high school friend Mitchell Queen. The enthusiasm of the fans, who at one point mobbed Pimp C and his wife, Chinara Butler, at a mall (“There were fifty to one hundred people running toward us,” remembered Butler), was rivaled only by the eagerness of other artists waiting to collaborate with UGK once again.

The self-titled Underground Kingz double album was released in August 2007 and debuted at number one on the Billboard 200. Featuring collaborations with some of the biggest names in rap, from Z-Ro and Talib Kweli to Rick Ross and Big Daddy Kane, the release cemented UGK’s dominance. Though the music touched on the usual topics of sex, cars, and drugs, it also ventured into unexpected territory, including questions of salvation and a call to stop glorifying the street life where “hustlers only hustlin’ to survive.” Their collaboration with OutKast, “International Players Anthem (I Choose You),” was nominated for a Grammy, and the accompanying video was named Video of the Year at the 2008 annual BET Awards. UGK was finally poised to claim the recognition and commercial success that had always beckoned.

Four months after the album’s release, Pimp C traveled to Hollywood to perform with the rapper Too $hort at the House of Blues. Pimp C sometimes indulged in a drink made popular in Houston called “lean” or “drank,” a cocktail of codeine cough syrup and soda, and on this particular visit he didn’t deny himself. Three days after the show, on December 4, he was found dead in a Los Angeles hotel, lying fully clothed on his bed. “I called the hotel to see why he missed his flight and to check on him,” said Chinara Butler. “At first I didn’t believe it, I thought it was a horrible story.” The cause of death was an overdose of cough syrup, which proved fatal due to a preexisting sleep apnea condition. Pimp C was 33 years old.

“Bun called,” said Ester Taylor. “He was crying on the phone, and he said, ‘He gone. He gone.’ ”

“I always say Pimp C is cigarettes,” Bun B said, sitting in a corner booth of a restaurant near his home, in Pearland. “I always want them. I quit smoking in 2000; I lost Pimp six years ago. And there isn’t a day that goes by that I don’t want a cigarette, and there isn’t a day that goes by that I don’t want to see or talk to him.” He cited Joan Didion’s book on the loss of her husband, The Year of Magical Thinking, and her observation that those left behind reflexively respond to interesting news or tidbits they’ve read by wanting to call the person they have lost.

“For him, it was cars,” he went on. “He was a big car guy. It would be like, ‘Man, I just saw the new Benz,’ or whatever. Now I’m into Gumball 3000 and F1 car culture, and I get to be among the most beautiful of cars. And all I ever think is, ‘Man, the dude would fucking love this.’

“Everyone always likes to say, ‘Well, he’s with you in spirit.’ Every now and then—I won’t say it’s him, but someone speaks to me about things. Not vocally, just ideas pop in.” He mentioned a flight he’d changed the previous day so he could meet a friend earlier than planned—a decision that proved prescient when his initial flight was canceled. “Had I stayed on my original flight, I wouldn’t have gone, wouldn’t have seen my friend,” he said. “Those are the things I feel he plays a hand in. Not any big dramatic thing, just little stuff. Like, ‘I know that’s where you’re trying to go, man. Leave a little early and you’ll make it.’ ”

Perhaps because he feels Pimp C’s loss so acutely, Bun B was more engaged talking about his best friend than when we discussed the music industry or himself, topics that led him to take a sip of his Sprite and mutter, “I hate work.” Still, he answered questions gamely, and when a fan approached our table, asking permission to share a link to his YouTube channel, Bun B was quick to nod. The young man scribbled the information on a piece of paper and pushed it toward him.

“Sorry to bother you, sir,” he said, sticking out his hand.

“Good luck to you, chief,” Bun B replied.

“I spent a lot of years of my life being very standoffish,” he said, turning to me. “So the last couple of years, I’ve been working against that, trying to be more personable. I spent a lot of years only talking about certain things with certain people, and now I want to talk about everything with everybody.”

Seeing his former partner’s life celebrated posthumously has informed this thinking. When Pimp C was alive, he said, “I saw how underappreciated he was.” But listeners’ recognition grew. “When he was gone, the entire history was laid out, his discography was laid out, and everything that he’d participated in was laid out, and then people realized, ‘Oh, shit, he wasn’t just a rapper.’ ” He paused. “So that’s what I’m trying to do: let people know now, before I’m gone, that ‘oh, yeah, he’s not just a rapper.’ ”

In Houston, where his evolution as an artist has coincided with an explosive cultural energy in the city, his forays outside hip-hop feel as natural as they do ambitious. Little wonder, then, that some have playfully suggested he run for office. In 2010 the rapper J. Cole endorsed him for the White House in a track called “Bun B for President.” Later that year, in a Houston Press poll, his hip-hop peers elected him Texas governor. Recently, there has been buzz about the more realistic idea of Bun B’s running for mayor, an idea proposed late last year by the Houston Press and quickly picked up by others, including political writer Charles Kuffner, who made a tongue-in-cheek list comparing Bun B’s attributes to those of Jesse Ventura and Al Franken. Noting the slogan that online commenters had already proposed—“Vote Bun B for Mayor and Keep Houston Trill as F**k”—Kuffner wrote, “You’d hardly have to campaign with a slogan as awesome as that.”

Bun B himself was initially dismissive of the idea, responding to a Press query in an email with “Too many skeletons in the closet, lol.” But a few weeks after the story ran, he revised that stance, telling MSNBC, “I don’t think I’m going to be able to run in 2015. It’s just not practical. I haven’t had any experience in the political world. If I would look to run for mayor, I’d start with city council, get the feel of local politics, get my hands dirty—not dirty, though—dip my feet in the water and get a feel for it.”

All of which sounded like a man considering the job, however distantly. In any case, the idea of an official post is, to many in the city, redundant. “I mean, he is the mayor to us,” said Kirko Bangz. “I don’t even know what the real mayor looks like, you know what I’m saying?”

A few minutes before Bun B took the stage, he pulled the Houston Press photographer, Marco Torres, aside. “Marco,” he said, “you’ve been there for a lot of my moments, but I’m very nervous.” Torres, at a loss for words at first, looked Bun B in the eye. “I’ve seen you happy and upset and angry, and now I’ve seen you nervous,” he said. “You handle every situation the way it needs to be handled, and I have confidence in you.” It sounded like something Bun B himself would have said.

With that, the rapper squared his shoulders and headed out. Bathed in red light, with the conductor and the orchestra and a choir from Lamar High School behind him, he took the microphone. In tribute to the night’s theme, “Concert Against Hate,” as well as its honorees—a collection of civil rights workers, Holocaust survivors, and educators—Bun B had written original lyrics to rap over the Black-Eyed Peas song “Where Is the Love?” As the violins and cellos established the melody, drums adding a heavy, funky downbeat, Bun B began:

Ladies and gentleman, boys and girls, tell me,

Are you happy with the current state of the world?

Tell me, do you look at the lay of the land,

And wanna wipe it all clean with the wave of a hand?

Do you look at the news on TV,

And feel like the drama’s unfolding in 3-D?

Did you read the morning paper,

And all that you saw

Was the evil that men do while breaking God’s law?

Are you tired of the ugliness you see every day?

Of Western civilization slipping away?

Of violence, discrimination, racism, and hate?

Wanna start it all over again with a clean slate?

Well, guess what, folks, it may sound strange,

But the power’s already in you to make change.

And tonight we honor those who fought the good fight,

And stood tall in the face of defeat for what’s right! All right!

He continued to the chorus, the choir backing him, as audience members began to clap to the beat. A new energy overtook him, and he strode back and forth, gesturing, careful not to look at his mother in the front row, who was watching with tears streaming down her face. (“I don’t know about you,” he said later, “but when I see my mom cry, I cry, so I had to find a different line of sight.”)

When he finished, the applause was reassuringly enthusiastic. Bun B left the stage and headed straight to his green room, where he briefly buried his face in a black towel. That night, he would finally get more than a few hours of sleep, and some days later, he would even take his wife on a vacation for her birthday before starting his months-long tour. But as he pulled his face away from the towel, he looked as if he was so relieved he might take a nap right then and there.

For the rest of the evening, he seemed to practically float backstage, and after the concert was over and the orchestra members were putting away their instruments, the conductor mentioned he’d love to work on another project with him. Bun B basked in the moment, pleased. Then he gasped—he’d forgotten something.

“Did the choir leave yet?” he asked. He’d assured the Lamar High School chorus that he’d take pictures with them, and now the students were nowhere to be seen. “They’re in the basement,” somebody said. As if he’d left a dignitary waiting, Bun B hurried to the stairs.

A few minutes later, he walked into the room of teenagers with a saunter, hands tucked into his pockets. The kids dove into their bags for their cameras and phones, scrambling, and as they mobbed him, his smile couldn’t have been brighter. Yes, he promised. He’d stay until every single one of them got a picture.