Coolio's 'Gangsta's Paradise': The Oral History of 1995's Pop-Rap Smash

How Stevie Wonder, Michelle Pfeiffer and "Weird Al" Yankovic played a role in the ubiquitous mega-hit

"Gangsta's Paradise" was not just a defining moment in Coolio's career, but also in the history of rap music and popular culture. Credit: Pablo Serrano/Corbis

During the last five months of 1995, it was virtually impossible to go anywhere without hearing the soulful, streetwise strains of "Gangsta's Paradise" blasting out of somebody's radio. Distinguished by Coolio's thoughtful lyrics and distinctive verbal flow, L.V.'s gospel-tinged wail and Doug Rasheed's starkly funky production, the song is a deeply affecting listening experience — and its hook, lifted from Stevie Wonder's 1976 track "Pastime Paradise," was absolutely impossible to shake.

Released in August 1995 in conjunction with the Michelle Pfeiffer vehicle Dangerous Minds, and boosted by a memorable video that featured the actress and various clips from the film, "Gangsta's Paradise" not only transcended its original soundtrack tie-in, but also managed to transcend the widely-perceived stylistic and commercial limitations of hip-hop. The single soared to the top of the pop charts in 16 countries, including the U.S., eventually becoming Billboard's Number One song for 1995 — the first time that a rap song had ever held the distinction of being a year-end chart-topper on the Hot 100.

But the accomplishments didn't stop there. "Gangsta's Paradise" won the 1996 Grammy Award for Best Rap Performance (it lost out to Seal's "Kiss From a Rose" for Record of the Year), and its video — directed by Antoine Fuqua, whose subsequent list of Hollywood credits includes the new Jake Gyllenhall film Southpaw — won MTV Video Music Awards for Best Rap Video and Best Video From a Film. The song also went on to sell over 3 million copies in the U.S. alone, earning triple-platinum status and inspiring the popular "Weird Al" Yankovic parody "Amish Paradise." (Coolio failed to share the public's appreciation for the spoof at the time, though that particular beef has long been quashed.)

On the 20th anniversary of the song's release, we asked some of the major players in the "Gangsta's Paradise" story to look back on what was not just a defining moment in Coolio's career, but also in the history of rap music and popular culture.

Doug Rasheed, producer: I was roommates at the time with Paul Stewart, Coolio's manager. Everybody used to come to our house all the time — it was a hangout spot.

Coolio: There was a studio at the house, so my manager's clients could come and work for free.

L.V., singer: Oh, that scene was beautiful, man! The Pharcyde, Tha Alkaholiks, King T, South Central Cartel, me, Coolio, the 40 Thieves — we all used to hang out there at Doug and Paul's place in Hollywood and just kick it, you know, have fun and produce music.

Rasheed: Paul was a DJ. He had a record collection and I had a record collection, so we used to see who could pull the hottest sample out. One day, I pulled out the Stevie Wonder record, Songs in the Key of Life, because that's one of my favorite albums. I pulled that sample out of "Pastime Paradise," and Paul was like, "Wow, that's tight!" So I decided to sample it and make a beat with it. L.V. was trying to get a deal at that time, so I was like, "Let's do it on L.V.!"

L.V.: I came in singing "Pastime Paradise," but then I changed it up to "Gangsta's Paradise." I did my parts, all the vocals and the chorus, and I did the choir. That whole choir that you hear was actually me — I did all the parts from soprano down to tenor to the bass. Doug and I were like, "Man, who can we get to rap on the song?" I asked my homeboy Prodeje from South Central Cartel to do it, and Prodeje told me, "Man, you should do it by yourself!" I said, "No, I want a rapper on it!" Prodeje didn't get on the song, so I thought of Coolio.

Coolio: I wasn't really familiar with "Pastime Paradise," as much of a Stevie Wonder fan as I was. My very first album I ever bought was the one with "Superwoman" on it. [1972's Music of My Mind.] I got that for my 12th birthday, that one and Fight the Power by the Isley Brothers. Songs in the Key of Life, my mother had that album at the house, so it was kind of weird that I didn't know the song. 

Rasheed: Coolio never liked my beats; he was always like, "Aw man, I don't like your drums!" But when he heard this, he said, "Doug, you did that?"

Coolio: I had actually gone over that day to pick up a check from my manager. I was getting ready to go back to my car — and I remember this clearly — there was a Chevy Biscayne that was parked next door; I was looking at that, and I was asking the neighbor if he wanted to sell it. And then I had to go to the bathroom, so I went back inside my manager's house to use the toilet before I rolled out, and that's when I heard the track. I walked into the studio, and asked Doug, "Wow, whose track is that?" Doug said, "Oh, it's something I'm working on." I said, "Well, it's mine!"

Rasheed: Coolio, at the time, had already had a hit record [1994's "Fantastic Voyage"]. We thought, "Man, this is an opportunity!"

"When Coolio wrote the lyrics, I was like, 'Wow, man, that's deep!'" —L.V.

Coolio: I sat down and I started writing. Hearing the bass line, the chorus line and the hook, it just opened up my mind.

"As I walk through the valley of the shadow of death/I take a look at my life and I see there's nothing left" — I freestyled that; that came off the top of the dome and I wrote that down. I thought about it for a minute, and then I wrote the whole rest of the song without stopping, from the first verse to the third verse. You know, I like to believe that it was divine intervention. "Gangsta's Paradise" wanted to be born; it wanted to come to life, and it chose me as the vessel.

L.V.: When Coolio wrote the lyrics, I was like, "Wow, man, that's deep!" Because what he was talking about was exactly what I was singing about.

Coolio: I did a couple of rough passes on the vocal, L.V. did a couple of rough passes on the hook, and I walked out of there with a cassette. I jumped in the car and I started calling people and playing it over the phone for them — "What you think about this?" The whole time I was doing it, I was like, "They're really gonna love this! This is a song for the neighborhood!" I called my A&R at Tommy Boy Records, and I played it for him. He said, "It sounds pretty good — I think it would make a good album cut." Those were his exact words! [Laughs]

Rasheed: Paul took the demo and shopped it to a couple of films, one of which was Dangerous Minds.

L.V.: I think the Martin Lawrence movie Bad Boys wanted it first, but they didn't wanna pay enough. And then Dangerous Minds upped the ante on the price.

Coolio: Four or five days after we recorded it, Paul was like, "We've got a meeting with Disney tomorrow — be there on time!" I called Tommy Boy; I had sent them a cassette, so they got to hear it first-hand, and their attitude was still, "Yeah, it would make a good album cut!" So I said, "You don't mind if Disney wants to use it for a film? It's no big deal — they just want to put it in some film they got." They were like, "Sure, go ahead!" I think we got about $100,000 for putting "Gangsta's Paradise" in Dangerous Minds. [Editor's Note: The Dangerous Minds soundtrack would eventually be released on MCA.]

Soren Baker, hip-hop journalist: I think "Gangsta's Paradise" resonated because of the song's video, which featured Coolio in a series of face-offs and stare-downs with Michelle Pfeiffer, the star of Dangerous Minds. This was a time when rappers weren't commingling with Hollywood A-listers — especially white female ones — so to see Coolio do it was striking.

Coolio: Here's the thing — Michelle was big, but the test-screenings of the movie were not going well. They were afraid that the movie was going to flop; they were terrified. They had snatched the movie off from testing, and they were trying to figure out what to do, because they had to put it out. I think they'd pulled it back for about a month. During that time, we went into the studio to re-record parts of "Gangsta's Paradise" — and even then, we weren't quite finished.

Rasheed: The song was recorded in four different studios, including my home studio; it just all came together to create a really good sound. But when I was doing the final mix, I said, "Something ain't right!" So I went in, I re-did the drums right there on the spot, and then I decided I needed to beef up the strings; within like 10 minutes, I re-did probably half the track. And then Kevin Davis, the mix engineer, put a blend on it; he couldn't have worked on it more than 15 minutes, and he was like, "Man, listen to that!" We said, "That's it, it's done!"

Coolio: But the thing was, we still had to get Stevie to sign off on it. When Stevie heard it, he was like, "No, no way. I'm not letting my song be used in some gangster song." So that was a problem. And it just so happened that my wife, she knew Stevie's brother — I guess he had been trying to tap that for years [laughs]. She made a call to him, got a meeting with Stevie and talked him into it. His only stipulation was that I had to take the curse words out. I had two places where I had the N-word in it, and two places where it was, like, "Fucked in the ass," or something like that. And Stevie said that if I'd take that out, he would sign off on it. Unbeknownst to me, the other condition was that he wanted 95 percent of the publishing! Had I known that, I'm not sure I would have went ahead with that — but I don't know, maybe I would have [laughs]. So that's how we ended up clearing it. Disney put "Gangsta's Paradise" in the movie, they started testing it again, and the test scores went from like 40 to 45 percent to 75 percent — 75 percent of the people all of a sudden liked this movie. That's when Disney started the marketing; they said, "We've gotta shoot a video!"

Antoine Fuqua, director: [Dangerous Minds co-producer] Jerry Bruckheimer asked me to shoot the "Gangsta's Paradise" video. I had full control. I wrote a treatment for the idea, and Coolio and the studio signed off on it.

Coolio: I wasn't completely happy with Antoine Fuqua's concept at first, because I wanted some low-riders and some shit in it; I was trying to take it 'hood. But he had a better vision, thank God, than I did. I couldn't completely see his vision, but I trusted him.

Fuqua: It was my idea to get Michelle [in the video]. I asked Jerry Bruckheimer if she would do it. He called her. She got on the phone with me. Asked me about my idea, and said yes. I couldn't believe she said yes. I had flashes of Scarface running through my head. She is one of the most stunning, beautiful women in the world, and turned out to be a very cool, nice lady, as well. Her and Coolio had fun shooting the video, I believe. It was a great experience for me, as well.

"I don't think that Michelle Pfeiffer had ever been around that many black people in her life." —Coolio

Coolio: Michelle was kind of nervous, because I don't think that, up to that point, she'd ever been around that many black people in her life [laughs]. And, you know, my boys were 'hood! But we had a good time. She came out and did her thing, and she killed it; it took her two takes to do her parts, and she was outta there. When I got the first edit back, I was like, "Wow, this could be big!" But let me tell you something — I had no idea that it was gonna take on the kind of life that it took. I totally was still thinking, in my mind, that it was gonna be a 'hood song. I was thinking to myself, "Man, with what's going on in the video and what I'm saying, there's no way white people are gonna get into this song. No way." But I was wrong.

Rasheed: I remember watching it climb; and then the week it hit Number Three, Michael Jackson came out with "You Are Not Alone," and it shot straight to Number One. I remember thinking, "Aw, it's over — we're not going to get to Number One!" And the next week after, we hit it, and we stayed on it for three weeks. It was a great moment!

L.V.: Paul Stewart called me to tell me that it was Number One. That was a big moment in my life, especially considering the different things that were going on with me at the time. My father was sick, my mother was sick, two of my brothers had died; yeah, there was a lot going on, man. The record came about at the perfect time.

Coolio: I was touring in Europe when it went to Number One. And the thing was, I was Number One all over the entire planet — not just in the States. I was Number One everywhere that you can imagine! I was like, "Man, these people don't even speak English, and they're loving the song like this?" That's what really tripped me out.

Baker: L.V.'s stark crooning and Coolio's raps about the street life were endearing to people who simply looked at Coolio as a party rapper. "Gangsta's Paradise" was a gangster rap song that had a quirkiness to it that appealed to people who would normally be put off by a traditional, bone-crushing gangster rap song. Coolio's quest for redemption in the song also likely resonated with people having the same questions about their own lives.

"Weird Al" Yankovic: My Bad Hair Day album was nearly complete — I was just waiting for inspiration to strike so I could write that ever-elusive hit single. Of course, since "Gangsta's Paradise" had been at the top of the Billboard Hot 100 for several weeks, by definition it was a prime candidate for a parody. I also liked the fact that it was a rap song — which means more words, which generally allows for more jokes — with a melodic chorus for the hook. Once I started toying around with "Gangsta's Paradise," the Amish concept hit me pretty quickly — I don't think I seriously considered any other options. "Amish Paradise" seemed a perfect irony — the Amish lifestyle is diametrically opposed to the Gangsta lifestyle, and I immediately saw a lot of comedic potential in rapping about life on the mean streets of Lancaster, Pennsylvania. I knew that for the video I would be doing a number of Amish-related vignettes revolving around my parody lyrics, but since the "Gangsta's Paradise" video was such an MTV staple, I knew that I needed to make some allusions to that as well. The scenes of Coolio and Michelle Pfeiffer were fairly iconic, so I decided to focus on those. I'm not sure exactly why, but it just made sense to me that I should recreate those scenes with Florence Henderson. . . and of course, she killed it. 

Fuqua: I was cool with it, because at the time there was no social media, and if Weird Al spoofed you, it meant you were popular or had a successful video. It was, funny. . . I guess.

L.V.: I didn't care, because Weird Al was doing everybody's song like that. Coolio didn't like it, though. 

Yankovic: There was a lot of he said/she said going on at the time [about whether or not Coolio had given permission to parody "Gangsta's Paradise"], and to this very day I don't know exactly how the lines of communication got crossed. And I'm still truly sorry that it upset Coolio so much at the time.

Coolio: I have to say, that was probably one of the least smart things I've done over the years. I should have never been upset about that; I should have embraced it like everybody else did. Michael Jackson never got mad at him; Prince never got mad at him. Who the fuck was I to take the position that I took? It was actually years later before I realized how stupid that was of me [laughs]. But hey, you live and you learn. Me and Al, we've been good for a long time now.

Rasheed: Our whole crew, Paul, Coolio and all of us, everybody just kind of went kind of crazy with the success of "Gangsta's Paradise." We all split apart; I worked with L.V. on his record, and recorded his version of "Gangsta's Paradise," but me and Coolio never did another record. Paul wanted to sign me to some contract that my lawyer told me was ridiculous, so I went out on my own. I won't get into any dirt, but I will say that things got a little bit nasty. Separately, we all did fine and we did well — my career's been great because of it — but I just felt like if we had stuck together we could have had a huge impact, instead of just a great hit.

Baker: "Gangsta's Paradise" proved that Coolio wasn't a one-hit wonder, and that he didn't have to deliver a prototypical radio record in order to enjoy success. The song also showed that gangster rappers could work with Hollywood's elite, and promote a film starring a white actress.

Coolio: You know what "Gangsta's Paradise" did, more than being one of the biggest sellers of that time? It solidified me in the rest of the world. It guaranteed that I could tour well into my sixties, if I wanted to. It's been very good for me, very lucrative, and it's gotten me to places that most rappers, no matter how big they get, they'll never go to some of the places that I've been to. You'll never see a Fetty Wap or a Future going to Pakistan or Uzbekistan, you know?

L.V.: I think "Gangsta's Paradise" continues to endure because of what the song is talking about — the song, and what Coolio's rapping about in the song, still pertains to what's going on in the world. I'll be talking to kids today who are like 19 or 20, and I'm like, "How do you know this song, when you weren't even one years old when the song came out?" These kids can still relate to the song because of the neighborhoods where they live, and the news they see on TV.

Coolio: I still get quite a few people coming up to me and telling me that "Gangsta's Paradise" got them through some really rough times in their life, and that it changed their life. A lot of people say it saved them from whatever demons they were dealing with, that they listened to the song and it helped them carry on; it saved them from suicide, all kinds of shit. A lot of guys told me it got 'em through their prison time. That's why I think of the song as divine intervention, because it doesn't even have the same meaning that it did in the beginning — it now means whatever you think it means. It has nothing to do with me; it has to do with whatever person is listening to it at the time. It's all things to all people.