Forever No. 1: Coolio’s ‘Gangsta’s Paradise’

Forever No. 1 is a Billboard series that pays special tribute to the recently deceased artists who achieved the highest honor our charts have to offer — a Billboard Hot 100 No. 1 single — by taking an extended look back at the chart-topping songs that made them part of this exclusive club. Here, we honor the late Artis Leon Ivey Jr., better known as the rapper Coolio, with an extended look at his lone Hot 100-topper: the gothic soundtrack smash “Gangsta’s Paradise.”

Precious little in Coolio’s career had suggested he would even entertain something so bleak as “Gangsta’s Paradise”.

“Do I have to use a gat to show you where I’m at?” he rapped on 1991’s Ain’t a Damn Thing Changed, as a part-time member of the conscious crew WC and the Maad Circle, “Or pose with a forty ounce and fake like a killer?” His 1994 solo debut It Takes a Thief was a West Coast party record that displayed a humorist’s touch: he rendered county welfare recipients and childhood ding-dong-dashers with the same twinkle. The big single was the No. 3 Billboard Hot 100 hit “Fantastic Voyage,” a G-funk banger that pulls to the curb and merrily ferries its audience out of gang territory.

In a contemporary profile in The Source, the Compton-raised Coolio (who had done some time as a juvenile, and kicked a cocaine habit before his rap career) talked about his motivation: “[W]hether this album goes platinum, gold or sells a few hundred thousand – I don’t care about me. I just want everything to be right for my kids. I’ve got to break the cycle for them.” “Gangsta’s Paradise” was the counterfactual: what if he couldn’t break the cycle? What would that feel like? What would that sound like? 

What it sounded like was perhaps the doomiest No. 1 in Hot 100 history. In title and structure, the song borrowed heavily from “Pastime Paradise,” Stevie Wonder’s 1976 unsettled chamber-pop rebuke of backwards thinking. Producer Doug Rasheed converted Wonder’s deliberate synthstring motif into slashes worthy of Bernard Herrmann and made the bass an ominous background figure. A squelchy clap on the 2 and 4 was the instrumental link to G-funk, but the overall vibe was positively gothic: Coolio’s midnight tour of decrepit buildings and broken brains. Unlike, say, Bone Thugs-n-Harmony — whose 1996 No. 1 smash “Tha Crossroads” offset their Old Testament existentialism with the promise of heaven – Coolio Crip walks through the valley of the shadow of death, unaccompanied.

But the trudge was a tour de force, as Coolio switches between high-handed taunts and head-clutching regret with a monologist’s deftness. He uncorks lines with Jules Winnfield’s Old Testament indignance (“But I ain’t never crossed a man that didn’t deserve it”) but also knows when to pull the punch. Specifically, the line “Too much television watchin’s got me chasin’ dreams”: he lands on a delicate blend of regret and wistfulness, sipping the poison like it’s the cure. His cadences and defiant introspection owed more than a little to Tupac Shakur, just taken to operatic heights.

If the result tipped toward melodrama, well, fine: “Gangsta’s Paradise” was written for the screen. Rasheed — who had a studio setup at the home he shared with Coolio’s manager — had been working on a “Pastime Paradise” loop with Larry “L.V.” Sanders, a singer and producer with the up-and-coming G-funk outfit South Central Cartel. Sanders had fleshed out the vocal arrangements (he mapped out every voice, bass to falsetto, in that mournful, soaring choral part) and was trying to get a rapper on the track. Coolio happened to hear the work in progress and immediately staked his claim, even writing a verse on the spot. With the demo done, Coolio’s manager began shopping it to film productions.

It was the percentage play: the ‘90s was a golden age for pop songs featured in movies, whether written for the film or added as promotion for an upcoming album. As a bonus, the soundtrack format — for movies aimed at Black audiences like Menace II Society, Above the Rim, and Juice — allowed nascent hip-hop fans to check out fresh names without having to rely on rap-resistant programmers in radio and television. Before he even had a solo album out, Coolio himself had three songs featured in the 1993 Janet Jackson/Shakur drama Poetic Justice. 

But Team Coolio’s best bet — Martin Lawrence and Will Smith’s action-comedy Bad Boys — fizzled when the musicians weren’t offered enough money. The winning film was another Don Simpson/Jerry Bruckheimer production: Dangerous Minds, a Bay Area classroom drama starring Michelle Pfeiffer. It wasn’t exactly the illest of movies (one scene has Pfeiffer teaching poetry to her Black and Latino students using Bob Dylan lyrics) but it had Disney money and the possibility of reaching a wide audience, which aligned with Coolio’s goals. In the context of the film, “Gangsta’s Paradise” offered a glimpse at the future bearing down on those students: “I’m 23 now, but will I live to see 24?/ The way things is going, I don’t know,” he shrugged. (Coolio, for the record, was by then in his thirties.) Ever the entertainer, he worried he was going “too dark.” 

It turns out he should’ve worried about going too blue. When Doug Rasheed reached out to Stevie Wonder for permission to use “Pastime Paradise,” the maestro rebuffed him. “I had a few vulgarities in the song and he wasn’t with that,” Coolio recalled. But Rasheed and Coolio was persistent, and Wonder finally signed off once the rapper agreed to overhaul the lyrics. (He also cedes the lion’s share of the publishing to Wonder.) Even with the foul language excised and his established rep as a pop-rapper, Coolio wasn’t sure white audiences would respond to “Gangsta’s Paradise”. 

His concerns were unfounded: the song entered the August 19, 1995 Hot 100 at No. 28: the week’s top debut. (That same week, the Dangerous Minds was the Greatest Gainer on the Top 200 Albums chart, jumping 108 places) By September 9th, “Gangsta’s Paradise” was No. 1, unseating Michael Jackson’s tremulous slow jam “You Are Not Alone.” Top 40 radio, at the time slower to put hip-hop singles into rotation, jumped on it. “Gangsta’s Paradise” had become the rap equivalent of a four-quadrant tentpole film, a hustler’s lament that kept expanding its audience. 

Arguably, Wonder’s demands contributed to the single’s reach. “Gangsta’s Paradise” was gangsta rap as message music, something kids didn’t have to listen to furtively. Coolio’s mean-mugging briefly became hip-hop’s acceptable face – making him, three years after The Chronic, the first L.A. rapper to top the Hot 100. For the music video, director Antoine Fuqua successfully recruited Pfeiffer to appear in the music video. Coolio figured he’d be getting the standard ‘hood video treatment, but instead, he got to glower in a darkened room at an A-lister, giving him and his song further credibility. “Gangsta’s Paradise” would win two MTV Video Music Awards the next year, for Rap Video and Video From a Film; if the Wonder lift hadn’t made the song ineligible, it would’ve been a shoo-in for an Oscar nomination, with an outside chance of beating Eminem to hip-hop’s first Best Original Song award.

“Gangsta’s Paradise” stayed in the penthouse for three weeks before getting evicted by Mariah Carey’s ecstatic (and tonal opposite) “Fantasy.” Though seven other singles had longer reigns in 1995, Coolio’s had remarkable staying power: it was either No. 1 or 2 for 12 weeks. Its run of play earned it the No. 1 spot on Billboard’s Year-End Hot 100 for 1995, the first rap single to top a Year-End Hot 100, and the only one until 50 Cent’s “In Da Club” did the same in 2003. And the global response was just as rapturous: in the United Kingdom, “Gangsta’s Paradise” debuted at No. 1, a first for a rapper. The single wound up topping charts in over a dozen countries. 

And it allowed Coolio to perform in dozens more, decades later. “Gangsta’s Paradise” functioned as a life annuity, guaranteeing its maker residual income and bookings long after most of his contemporaries changed careers. For subsequent generations, ”Gangsta’s Paradise” wasn’t just Coolio’s signature song, it may as well have been his only one. It has over a billion plays on YouTube and Spotify; on the latter it has fifty times the streams of “Fantastic Voyage,” his next-most popular track. His time at the vanguard of mainstream rap lasted just a brief while: 1995’s Gangsta’s Paradise album spawned one more Hot 100 top five hit in “1, 2, 3, 4 (Sumpin’ New)” — which, ironically, found him back in party-MC mode — and his U.S. hitmaking days ended with 1997’s treacly gospel ballad “C U When U Get There,” which peaked outside the top 10 and marked his final entry on the chart. 

“I can’t live a normal life,” Coolio fretted on “Gangsta’s Paradise,” and it proved true as he transitioned to a long second career in acting and reality television. To the end, he was a celebrated link to West Coast rap’s breakthrough age and a touring shot of instant nostalgia. And though he didn’t get to be an elder statesman for as long as we might have hoped, he had long since shattered the cycle that had consumed his thoughts before he used it to top the charts.