"Gangsta's Paradise" at 25: How the smash hit came to be

Rapper Coolio talks to Yahoo Entertainment about how his smash hit, "Gangsta's Paradise" came to be. He explains how Stevie Wonder signed off on the sample usage, Wonder's involvement in their performance at the 1995 Billboard Music Awards, and the feud that sprung up between him and "Weird Al" Yankovic after the parodist released his "Amish Paradise" spoof.

Video Transcript

[MUSIC - COOLIO FT. LV, "GANGSTA'S PARADISE"]

Been standing most their lives living in a gansta's paradise.

LYNDSEY PARKER: Hi, Coolio, thank you for joining me today. I'm really excited to speak with you. We have a big anniversary this week. We are coming up on the 25th anniversary of "Gangsta's Paradise," which came out August 8, 1995.

And it was the biggest single of the entire year. So I guess the obvious question to start with was, did you know what you had on your hands? Did you know it was going to be this big of a monster hit?

COOLIO: I was pretty excited about it, to tell you the truth. When I let the record company hear it, their exact words were, oh, yeah, this is a good album [INAUDIBLE]. Swear to god, they say that. They will-- they will deny that right now.

LYNDSEY PARKER: [LAUGHS]

COOLIO: Because they denied it shortly after that. If you think about it, if they would have thought that it had been a monster hit like that, there's no way they would have let it be on a soundtrack.

LYNDSEY PARKER: Interesting.

COOLIO: There's no way they would [INAUDIBLE] sharing the revenue of that. You feel me? They didn't see it. They didn't have the vision. Yo, there was a lady named Kathy Green, she did acquisitions for Disney at the time, for Disney-- she did acquisitions for Disney films.

When she heard "Gangsta's Paradise," she froze. She didn't say a word. It played to the end. She stopped it.

She replayed it. She's like, oh my god, I love this song. It would be perfect for this movie that I'm working on.

LYNDSEY PARKER: How do you feel that movie, "Dangerous Minds," has aged? Because I feel like that movie now seems a little antiquated, you know.

COOLIO: To be honest with you, I hate those kind of movies where, you know, the great White hope comes into the inner city neighborhood and saves the little children-- oh, la, la, la, hey, Santa Claus, or, you know, whatever. Everybody knows that those kind of moments happen very few and far in between. And nobody-- nobody-- there's not that many people that care about each other. Hey, I'm not saying this is unheard of. But just, you know, those kind of movies are cliche as hell.

LYNDSEY PARKER: What was your perception of the movie 25 years ago compared to now?

COOLIO: I knew that the song being in the movie helped the movie. And I knew that the movie having the song in it helped the song, gave it a better chance than it would have had on its own. They both helped each other. Because the movie was not testing well. And they anticipated it to be a flop.

I thought it was going to be Michelle Pfeiffer's first flop. They were scrambling trying to do whatever they could to make that not happen. I mean, it was testing very low. When they put the song in it, it gave it that emotional and human element.

LYNDSEY PARKER: Tell me your memories of making the music video, where you're sitting so iconically with Michelle Pfeiffer.

COOLIO: At first, I didn't think she was going to show up. And when she showed, I was, OK, she's not scared. I thought she was going to be scared.

LYNDSEY PARKER: [LAUGHS]

COOLIO: She brought her twins with her. She had just had twin babies. They dolled her up real quick. And you nailed it. I mean, she got it.

It was as easy for her as it was for me, I think. We talked very little. We didn't talk a lot, you know, hi, how you doing. I asked her a couple generic bull-[BLEEP] questions and just small talk pretty much. And she was in and out.

Like I said, she had her babies with her. So to tell you the truth, she wasn't that interested in what was going on. She just came-- somebody asked her to do something. She came in, she nailed it. And she went back to mommy duties.

LYNDSEY PARKER: So, obviously, this samples a Stevie Wonder song. So how did it come together that you did perform with him at, I believe, it was the Billboard Music Awards that year? Tell me your memories of that.

COOLIO: Stevie Wonder, I mean, you know, man, it was like I was on drugs. It was a high. It really was.

I had so much power that night in my voice. And I had so much my breath control and my stage presence was probably, you know, 15 to 26, whatever. It was-- it was different.

LYNDSEY PARKER: Which was like, I'm trying to remember when he starts singing his own hook.

COOLIO: Yeah, he starts singing, "Pastime Paradise." And then they started saying, ain't no racists living in paradise. And LV was saying, ain't no gangstas living in paradise.

And then he was saying, ain't no racists living in paradise. And, you know, they just-- they just started ad-libbing, kind of like doing runs. It was tight.

LYNDSEY PARKER: Well, there's another iconic performance that you did of this song with Howard Stern, when you went on his show and sang. And he ended up singing the LV hook.

HOWARD STERN: [SINGING] Been living most our lives living in a gangsta's paradise.

LYNDSEY PARKER: So when he starts singing on the track when you performed it on his show, did you know-- was that planned? Or did he just start singing it like on his own?

COOLIO: He started singing it on his own.

LYNDSEY PARKER: [LAUGHS] He actually sounded all right, like mostly on pitch.

COOLIO: I-- wasn't bad at all. I always liked Howard. He can be offensive. He can be crass and rude, almost borderline racist sometimes. But, you know, it don't bother me because it's OK to be who you are, you know.

He means well is what I'm saying. He always been cool with me. You know, he's always supported my music. And I overlook the stuff about him that I don't like. You always have friends or family or, you know, people that do things-- you like people, but you don't like everything they do.

LYNDSEY PARKER: No interview about "Gangsta's Paradise" would be complete without asking about what happened with Weird Al. I know you guys did patch things up. But I want your side of the story about what the miscommunication was.

COOLIO: They asked me if they could do it. I said no. They did it anyway. I felt disrespected. But in hindsight, that was not one of my most cerebral moments, OK.

I was-- that was hella dumb of me. You know, he did Michael Jackson. He did a bunch of people of much higher stature than me. And, you know, I should have just let it go.

LYNDSEY PARKER: I think you've been quoted as saying it was one of your biggest like career regrets is that you objected to it or whatever.

COOLIO: Not career regrets. But it was one of the dumb things I did. It made me look petty, and shortsighted, and dumb, and ghetto, and-- and, yeah, all of the above. Check off every box. It wasn't cool.

And I'm supposed to be Coolio. It wasn't Coolio of me to do that. In hindsight, you know, especially after I thought about it and then I talked to some friends and some family, it was like, man, what's wrong with you? That was that. And I was embarrassed.

I embarrassed myself. I just told him, I said it's cool, bro. I'm sorry about all the-- all the hoopla. You know-- you know, is it cool?

He's like, yeah, it's cool, man. Don't worry about it. I was like, yeah, you don't worry about it neither. I think that's what we said to each other before we turned back to back.

LYNDSEY PARKER: Did you ever perform together or talk about doing that?

COOLIO: No, we haven't.

LYNDSEY PARKER: I think for the 25th anniversary, maybe do a virtual Zoom, you know, live stream of "Gangsta's Paradise" mashed up with "Amish Paradise," not a bad idea.

COOLIO: Mmm-mm, mm.

LYNDSEY PARKER: [LAUGHS] Giving you that idea. Run with that, if you want.

COOLIO: It's totally possible because, you know, "Gangsta's Paradise" is not mine anymore. It's everybody's.