(September 30, 2022).  When then-up-and-coming rapper Coolio (real name Artis Leon Ivey, Jr.) borrowed the haunting melody of Stevie Wonder’s “Pastime Paradise” for his own song in 1995, it was somewhat of a risk.

First, despite Wonder’s legendary status, the Motown icon’s classic blend of pop and soul hadn’t often been sampled for hip-hop hits (at least not at the time).

Secondly, it was “Pastime Paradise,” a brooding and somewhat forgotten song from Wonder’s then-two-decades-old Songs In The Key Of Life album…a song with an infectious-but-eerie synth-violin whose oddness was eclipsed only by the use of two choirs—one gospel, the other Hare Krishna—whose joint chants at the end sounded like an urgent African call to the gods.

Those traits hardly seemed to be the makings of a hip-hop classic, especially coming from the West Coast, where ‘70s funk-inspired gangsta-rap from the likes of fellow Californians like Dr. Dre, Snoop Dogg, the Dogg Pound, and Ice Cube ruled the day.  

But Compton-raised (and Pennsylvania-born) Coolio saw in “Pastime Paradise” what few others (besides maybe Stevie himself) did.  For the messages he intended to deliver, “Pastime Paradise” provided Coolio with the perfect ominous backdrop.

Stevie Wonder’s “Pastime Paradise” (1976)

“Pastime Paradise” ultimately became “Gangsta’s Paradise,” a haunting but cautionary tale about a gun-toting kid from the streets who wondered aloud if he’d live to see his next birthday.  The song was recorded for the Michelle Pfeifer-starring movie Dangerous Minds, in which she portrayed a heroic teacher in a tough, low-income high school full of underachievers.

Coolio’s “Gangsta’s Paradise” (2005)

The movie was a success, but “Gangsta’s Paradise” was arguably bigger.  The song’s compelling imagery and the eerie Stevie Wonder music behind it worked phenomenally.  Not only was “Gangsta’s Paradise” a smash hit, but it shot to No. 1 in the late summer of 1995 for three weeks (displacing Michael Jackson’s last chart topper, “You Are Not Alone”).

At the time, only five hip-hop songs had ever hit No. 1 on the Billboard Hot 100, so Coolio’s accomplishment was no small feat for a genre that was still burrowing its way into the mainstream.  And none of the previous five (“Ice Ice Baby,” “Good Vibrations,” “Set Adrift on Memory Bliss,” “Jump” and “Baby Got Back”) came anywhere close to touching on the hardened street themes “Gangsta’s Paradise” explored.

Thus “Gangsta’s Paradise” was gangsta rap’s first No. 1 single on the Billboard Hot 100.

But it was what Coolio’s smash pulled off several months after it topped the weekly charts that was truly historic.  

That December, when Billboard tallied its year-end list of 1995’s biggest hits, “Gangsta’s Paradise” ranked at No. 1.  No other hip-hop song had ever finished as the year’s biggest hit prior to Coolio’s.

Billboard’s top songs for all of 1995

Before then, the closest any rapper had come to having the top song of the year was in 1992 when “Baby Got Back” by Sir Mix-A-Lot finished at No. 2 (and Kriss Kross’ “Jump” finished right behind him at No. 3).

“Gangsta’s Paradise” stood as the only rap song to top a Billboard year-end chart for the next eight years, until 50 Cent joined the exclusive club with his first No. 1, “In Da Club” in 2003.

After Coolio and 50, the only other rap acts to take year-end top song honors to-date have been Flo-Rida featuring T-Pain (“Low,” 2008), Macklemore and Ryan Lewis (“Thrift Shop,” 2013), Drake (“God’s Plan,” 2018), and Lil Nas X (“Old Town Road,” 2019).

For perspective, that’s just six rap songs to top Billboard’s biggest-hit-of-the-year tally in the 43 years that rap music has been charting nationally, with the last five hits happening in the past twenty years.

Biggest song of the yearYear it topped the chart
“Gangsta’s Paradise” by Coolio1995
“In Da Club” by 50 Cent2003
“Low” by Flo Rida ft. T-Pain2008
“Thrift Shop” by Macklemore and Ryan Lewis2013
“God’s Plan” by Drake2018
“Old Town Road” by Lil Nas X ft. Billy Ray Cyrus 2019
Data courtesy ‘Billboard’ magazine

“Gangsta’s Paradise” eventually sold more than five million copies in the US (and equally as well internationally).  For 1995’s year-end No. 1 spot, it beat out some formidable competition by TLC (“Waterfalls” and “Creep”), Madonna (“Take A Bow”), Seal (“Kiss From A Rose”), Mariah Carey (“Fantasy”), and Boyz II Men (“On Bended Knee”).  “Paradise” won Coolio a Grammy for Best Rap Solo Performance at the following year’s ceremony.

Coolio was born in Monessen, PA and raised in Compton, CA

Coolio, whose famous braided locs made him a striking figure, would go on to have a few more chart hits after “Gangsta’s Paradise.” He reached the top ten once more with “1, 2, 3, 4 (Sumpin’ New)” and had preceded “Paradise” with a No. 3-peaking interpolation of Lakeside’s funk classic “Fantastic Voyage” in 1994.  None of those songs, however, matched the success of his groundbreaking No. 1 single.

Unfortunately, Coolio also faced some personal demons after the hits stopped coming.  Although he had overcome drug-related issues pre-fame, his legal woes—including convictions for robbery, causing bodily injury and illegal firearm possession—landed him with fines and probation on multiple occasions post-celebrity.

But he also became a prolific actor and TV personality with more than 50 movies to his credit and nearly as many TV appearances where he often portrayed himself or a similar character.  Most notably, he starred in the TV series Cookin’ with Coolio, which showcased the rapper’s well-honed cooking skills and saw him branding himself as the “ghetto Martha Stewart” or the “Black Rachel Ray.”

To put it simply, Coolio was a multi-media entertainer whose transition from the streets of Compton to international superstardom was the kind of stuff kids—especially poor Black ones—could hardly imagine, much less realize.

That he was able to escape the confines of the very narrative he rapped about in “Gangsta’s Paradise”—one that too often describes the plight of young rappers even today (especially today!)—was a minor miracle in and of itself.

Coolio’s next birthday would have been his 60th.  As hip-hop is still relatively young (compared to other genres), and with the death rate of rappers seemingly being higher than that of other musicians, few big-named MCs have lived to see that 60th milestone.

While no cause of death has been officially named and his death is not being investigated as a homicide, that bleak life-expectancy backdrop makes Coolio’s sudden passing on September 28 at age 59 just that much sadder.

But his legacy will live on with a catalogue of unforgettable hits from hip-hop’s most expansive era (the 1990s), and a mood-shifting, groundbreaking smash that became not only the first gangsta rap No. 1 ever, but the first song in hip-hop history to be named the top hit of the year in Billboard.

Not bad for a “loc’d out gangsta and set-trippin’ banger with a ten in his hand and a gleam in his eye.”

Rest in peace Coolio (August 1, 1963 – September 28, 2022).


DJRob (he/him/his) is a freelance music blogger from somewhere on the East Coast who covers R&B, hip-hop, pop and rock genres – plus lots of music news and current stuff!  You can follow him on Twitter at @djrobblog.

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By DJ Rob

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