As a solo artist, Cool C’s biggest hit toasted to the “Glamorous Life.” Signed to Atlantic Records, the West Philadelphia MC born Christopher Roney had come a long way from rapping in the hallways of Overbrook High School with classmates, the Fresh Prince (Will Smith) and Steady B. Among the first Philly artists to sign to a major label, Cool C drove around town in a kitted SUV with his hit’s title written across the side for all to see. His release artwork and music videos featured truck jewels, cars, stacks of cash, and his beaming smile. In the moment, Cool C was on top—from the Hilltop, the name of his street/rap conglomerate that also included Steady and Three Times Dope.

Eight years later, in the morning of Jan. 2, 1996, things were not so grand. Cool C, his mentor and producer Steady B (Warren McGlone), and friend Ernest Mark Canty waited in a stolen green minivan for the door of a PNC Bank branch in Feltonville—a gritty working-class neighborhood in North Philadelphia—to unlock. In the 15 minutes that followed, the men, dressed in construction worker outfits, would enter, point weapons at three bank workers, demand the vault be opened, and attempt to perform a robbery. However, they would not steal a single bill. In the attack, a silent alarm was pressed, notifying local police. The first to respond was nine-year force veteran Officer Lauretha Vaird, who entered, reportedly wearing a bulletproof vest without its preventative inserts—only to be ambushed in the doorway and killed.

All three culprits remain in prison, though Roney, who was determined by a court of law to be the one who fired the fatal shot to the abdomen—killing a 43-year-old single mother of two—is the only one fighting for his life. When he was convicted of first-degree murder (along with other charges) on Oct. 30, 1996, Roney, 26 years old at the time and with no criminal past or motives, maintained his innocence, along with the fact that he was home cooking breakfast for his mother, who corroborated this alibi. In March 1997, a jury would ultimately decide to sentence Roney to death by execution. After a series of appeals ending in a 2005 Pennsylvania Supreme Court ruling, the verdict remained. Then-Gov. Ed Rendell would sign a death warrant one year later, followed by a stay of execution. In November 2014, Pennsylvania Gov. Tom Corbett signed the latest warrant for Roney. Early this month, for the second time, Roney was given an emergency stay of execution before the Jan. 8 date, indefinitely postponing the now-45-year-old’s capital punishment "until the completion of all federal litigation pertaining to his Petition for Writ of Habeas Corpus," per court documents. One of rap music’s uglier chapters—which truly has little to do with music—is unfolding before the world’s eyes.

Nineteen years to the week since the robbery and murder, little has changed in Feltonville. On the 4700 block of Rising Sun Avenue, the PNC Bank continues to operate, while nearby businesses feature boarded-up windows next to trash-littered sidewalks. The area, two easy turns from the Route 1/Roosevelt Boulevard thoroughfare, now features a Boys & Girls Club center named in Vaird’s remembrance. The set of double-doors she entered on that fateful day still stand.

Although less heard today beyond the city, Cool C’s breakthrough remains a classic in the City of Brotherly Love. “Glamorous Life’ is still a hit,” says DJ Too Tuff. “It’s right next to ‘My Part of Town’, one of the all-time greatest Philly party records.” A founder of the Tuff Crew, the DJ/producer remains a pioneer of the city’s hip-hop scene, and someone who performed shows alongside Cool C, Steady, and Three Times Dope. “It was a friendly competition. They would always make us be at our best,” says Too Tuff, who grew up in the “Badlands” section of North Philadelphia also known as “The Danger Zone,” rivaling the emerging voices from across the Schuylkill River, in West Philly. An active, working DJ to this day, Too Tuff enjoyed Cool C’s catalog. “I definitely bought and played it. I liked more of his harder stuff,” he adds, pointing to songs like “Enemy Territory” and “Down to the Gristle.” Whereas the (recently reunited) Tuff Crew worked arm-in-arm with New York innovators like the Ultramagnetic MCs and Tim Dog, Cool C gained notoriety for boldly dissing one of rap’s most talented outfits, MC Shan, Roxanne Shante, and the rest of the Juice Crew, with his debut, I Gotta Habit. With many members of the Juice Crew first appearing on the Philadelphia Pop-Art label, tied into Cool’s then-manager Lawrence “L.G.” Goodman, the jab was presumed political as much as competitive.

Cool C and the Hilltop Hustlers were like gods to me. When people from your city succeed, I think it gives you confidence to follow your dreams. —Vinnie paz

Vinnie Paz of Jedi Mind Tricks and Army of the Pharaohs fame, an adolescent in the days of Cool C’s debut and 1990 Life in the Ghetto follow-up, recalls the impact. "Cool C and the Hilltop Hustlers were like gods to me. When people from your city succeed, I think it gives you confidence to follow your dreams, [which] somehow seem more realistic,” says Paz, who was a mainstay on the Top 200 through his solo work and groups. “I bought I Gotta Habit the day it came out in August of ’89 on 69th Street. I love that fucking record.”

A star in 1989 and 1990, Cool C's time in the music industry limelight was ephemeral. The West Coast G-Funk movement took the spotlight in the early 1990s. Jeeps—like the one Cool drove around town—gave way to candy-painted ’60s Chevrolets, Timberlands and Ballys gave way to Converse Chucks, the skyscraper shadows yielded to life in the sunshine. Along with a seemingly antiquated sound, drugs were also a carryover from the 1980s for many rappers in Philly. “[At that point] everybody was into the drug life, whether sellin’, gettin’ high, or both,” admits Too Tuff, who points that “woolies” or “turbo”—a blend of marijuana and crack cocaine—was especially prominent, something Schoolly D also touted in the ’80s documentary Big Fun in the Big Town. Whether or not addiction played a factor for the artist who made I Gotta Habit may never be known.

What is known is that Cool C tried to stay in step with the times. Like Run-DMC and Naughty by Nature, C and Steady B rebranded themselves in the mid-’90s hardcore hip-hop era, the tragically ironic group name of C.E.B. (Countin’ Endless Bank) doubling as the members’ initials. The trio (with Eric “Eaze” Ponder), released one self-titled album in 1993 on Ruffhouse Records and sold a reported 15,000 copies. A video at the time with Steady B, an empty auditorium, and a shifty promoter suggest the rappers’ declining status.

Less than three years later, it is only presumable that things had worsened. At the time of the 1996 robbery, C.E.B.’s third member was incarcerated for a kidnapping conviction. Cool C and Steady B, once decorated lyricists, had turned to heists. “What [people in the streets] had heard was that they were robbin’ banks long before that,” Too Tuff recalls, though he adds that those reports were never substantiated. A fighter who managed to stay relevant and profitable as an artist, the DJ reflects, “One of the hardest things in this world to be is famous and broke.” He adds, “To put my mindset in what was goin’ on, it must have been insane.”

“They were only two or three years removed from their last ‘hit,’” notes Vinnie, referring to the video single “Get to the Point.” “In some way, that was the day that I realized the music business was all smoke and mirrors,” he says. “I wish that day never happened.”

Lauretha Vaird’s sons, Michael and Steven, painfully must agree—and following psychiatric therapy after their mother’s murder, have not minced words in favor of Roney’s execution. Presumably, Steady B and Mark Cantry—both currently serving life sentences for second-degree murder and other charges following their confessions—must also want that January day back. Cool C, whose own life hangs in the balance of politicians and a potential courtroom, has to wish for the fateful do-over as well. Per reports, the murder weapons, a 9mm pistol and a silver handgun left in the getaway, led Philadelphia police investigators to McGloney. Although often reported as arrested days after the robbery-murder, Roney turned himself in to authorities following an arrest warrant. The third accomplice, Canty, would be arrested in a traffic stop in Maryland later that year. Surveillance video, along with three witnesses—including a Philadelphia police officer outside the bank involved in the shooting, a passerby, and a bank employee—helped to identify Roney. Additionally, Steady B’s wife, Lynette Medley, testified that the three men met in her apartment in the evening of Jan. 2 to watch the televised reports. Meanwhile, Roney, and his mother, Barbara, maintain their alibi, and in turn, Cool C’s innocence.

Following the 1996 signing of the death warrant, Cool C has spoken little publicly. In 2006, the year the first stay of execution was ordered, he wrote to XXL magazine from a Waynesubrg prison cell, “My mood remains strong, positive, and faithful daily…. My thought when the warrant was signed was, ‘Why?’ I have more appeals; and they are my rights that I am going to fully exercise to get a new trial and acquittal, despite what media and society thinks.” In preparing this story, messages were left with Roney’s sister, but not returned. Previously, she and the rapper’s mother have spoken before courts and media, defending their kin. In the 1996 trial, 22 people reportedly testified before the courts on behalf of Roney’s character. Much of Cool C’s family remains near the Hilltop that earned him fame, as a skilled lyricist who gave others hope, ambition, and an escape to the glamorous life. Twenty-five years later, Christopher Roney simply wants life, and to escape death row.

Jake Paine is a writer living in Pittsburgh. Follow him @PaineInVain.