Jason Little from 90’s R&B Group Ol’ Skool Shares His Frustrations With The Business; Talks Solo Comeback

What happened to the 90’s R&B group, Ol’ Skool? Group member, Jason Little breaks it down!

The music industry is not for the faint at heart. For every success story, there are hundreds that don’t make it. Dan Seals sang “Everything that glitters (is not gold).” Being a part of an R&B group in the ’90s with a hit song on the radio, you would assume that life was good for Jason Little and his group, Ol’ Skool. But… everything that glitters is not gold. Ol’ Skool released their self-titled album in 1998, followed by their sophomore effort “RSVP” a year later, and then they went quiet. Their hit, “Am I Dreaming” featuring Keith Sweat and Xscape from their debut album seemed to be the beginning of something special. Instead, the group dismantled and became obscure on the music scene.

I caught up with, Jason Little from the group who opens up about the group’s breakup, homelessness and his efforts to return as a solo artist.

How have you been?

Jason Little: I’ve been good, man. Just trying to work hard, man and stay moving. You know that can be. It’s a tough industry. So, really just trying to make it do something (laughing).

Are you in touch with the fellas? Are you trying to come back as a group or a solo artist?

Jason Little: Actually, we came back as a group in 2017, man. It was a straight disaster to be real. It didn’t work out. Everyone stays in different places. I’m in Atlanta. One of the guys stays in New York and the other two are still in St. Louis. So, we got together and started rehearsing and it just wasn’t good, man. It was not good.

You guys were all very young, new to the game, do you think too much time had passed or was it something else that made the comeback attempt unsuccessful?

Jason Little: Not really. I noticed that when we were together at first, some of the same issues were still there. But I think they were worse. Just dealing with the members of the group and all the issues the group has with one another. It’s hard to sing with guys first of all. A whole lot of egos. We kind of didn’t mesh well. I’m the talk of person… I’m really laid back, one of the other guys is laid backed also, and then you mix that with egos. It just wasn’t good. When we broke up, I think we broke up in 2003. I have always wanted to get the group back together since that time, but so many different things happened. I moved to New York around 2004. I was doing a lot of things, so I would always talk about the group and try to get things going and they were people interested. So, I would try to call back home and get the guys together, but they didn’t want to do it. I had a possible show at the Apollo, they didn’t want to do it; a few other things going on, they didn’t want to do it. It would always frustrate me because I knew as a group, it would be better than us trying to do it solo. It was just really frustrating.

It sounds very frustrating

Jason Little: So, what I ended up doing, I ended up being a background singer for Trey Songz. I started doing that and doing all the TV shows with him and all that. Well, I jumped the gun a little bit, first of all, I ended up homeless. And then I randomly going with a friend of mine… I guess he kind of had an audition with a group Carl Thomas was putting together. I just happened to be there. I was minding my own business. I’m real laid back. I’m not one of them guys trying to show off. I was letting him do his thing, I’m sitting there minding my business and the guys were like, “What you do?” I told them I sing. We started singing and they liked me. So, they asked me to get in the group. To make a long story short, we went to Carl Thomas house and met him and talked to him. We went to record a song at Troy Taylor’s house. Troy is the guy that discovered Trey Songz. He’s also the CEO of Songbook Entertainment, who Trey is signed to. When I went to that house, that’s where I met Trey Songz. He was there and at the time he was like 19 or 20.

I did that for a couple of years and then after that, I ended back up on the streets because I didn’t have a job and I couldn’t find a job. I lost a lot of weight. Just trying to figure out my way and ended up going back to St. Louis. But the whole time I was trying to get, Ol’ Skool back together and just trying to get the guys on one page and trying to do something where everybody can eat.

The group’s first album was amazing. Self-titled, it dropped in 1998, the RSVP album came a couple of years later and then we kind of didn’t hear from you guys for a long time. What happened?

Jason Little: A lot of things… the fellas were upset about and rightfully so. We weren’t making no money. We were signed to Keith Sweat/Universal. Videos would be on television, but nobody had a car; barely could eat. So, you get what I’m saying. It made it a very frustrating situation and I understand that. we did a second album as you mentioned, but the guys were so unhappy by then. I was talking to Katina Bynum at Universal, now she is the Senior VP of Universal Republic and Cash Money. Actually, I still talk to her. We all do from time to time. One day she had called me and said, “Hey, we’re about to send you guys to Europe.” So, I’m excited about that because I knew, things weren’t going too good over here, but maybe over there it would go good. Next thing you know, one of the guys in the group hit the manager up to tell Keith and the label that we just wanted out of the deal. I didn’t even get a vote in that and just like that it was all over.

I do understand why they were unhappy. Someone else getting all the money, you’re not getting nothing. Holidays come up and you can’t get your kids anything. You don’t have a car. Literally could barely eat and I get that, but also at the same time I always knows that things can turn around at any moment. When she told me that they were getting ready to send us to Europe, I looked at that as an opportunity that we could make something happen. But everybody gotta want to do it. I also learned singing in a group, everybody had different drives. I have always been the type of person that… I guess it’s stubborn. I would not stop. I would keep going and try to work a situation. Man look how many guys wish they were with a record label. We could turn this thing around. Everybody gotta want to do it though. That’s what ended up happening. We were supposed to try to get another record deal, but after we broke up, nothing. Everybody just went their own separate ways. That’s what made me move to New York because I’ve always liked New York, so I went out there to try to work on solo stuff. Running into Trey and meeting them and doing that, but that’s how that whole thing happened.

I love the show, “Unsung.” Everything you just said seems to be the issue with a lot of groups that find themselves on that show. The money didn’t add up to the product and the content being put out. The perception is, if you’re on television you’re making money and that’s not always the case.

Jason Little: Yep! It can be bad, man depending on who you hook up with. I don’t fully understand it, but I also know, sometimes when people sign artists, they can make a lot of money off that artist. Just think, I’m the big time R&B guy and I sign a group, and I got a label deal with Atlantic or Universal, they may cut me a $600,000 check for my group and I’m in control of it. I could just give them some peanuts, couple thousand and I get to keep the rest and do whatever. That’s what happens a lot and it’s sad, man. That part, I understand why everybody was upset. They wanted to leave; they weren’t happy with Keith. Another thing too, the label really wasn’t pushing us. It was a lot of situations where they kind of needed Keith’s blessing or his co-sign and they would be trying to get in touch with him and he wasn’t hitting them back, so it had us kind of stuck. They were like, “We don’t really know what to do with ya’ll right now. Keith is not hitting us back.” Now, if we would have been signed straight to Universal or any other label, it could have possibly been a little different because they could just move how they want to move. But we were signed to Keith, so if he’s not responding, we’re just sitting.

“Am I Dreaming” is still a classic song even right now. You had a Keith Sweat and Xscape feature on that one. How did that come together?

Jason Little: Basically, it was going to be Keith and Xscape. But Keith Sweat had loss Silk. Whatever happened with Silk, he wanted another group and he got, Ol’ Skool. It was cut with them and somewhere along the line I guess Keith said, I got a group coming out, I’m gonna cut it on the group. That’s really how that came about. It was all Keith Sweat. The whole song, his idea… that was his thing. He the one put the group on it. Which to me was a brilliant idea. That was cool.

When it’s all said and done, what would be the ideal ending for you?

Jason Little: For me, it’s just to get where I have always wanted to musically go. Even before, Ol’ Skool it’s always been a dream of mine to be an inspiration to people. Now, we’re older and I’ve heard so much over the years; before Ol’ Skool after Ol’ Skool. Things like, You’re too soulful, it’s about the younger kids, you’re too dark. I heard that before years ago. “The ladies seem to like light skin or brown skinned guys.” I’ve heard I’m too dark and… (getting emotional) just to be an inspiration to people. No matter what, just keep going. Man, I done been homeless for this stuff. I’m talking about, sleeping in Central Park, sleeping in the Penn Station all for music. And then for somebody to say, “You sing too hard,” “You’re too soulful,” but I know if you keep going, you can make it. That’s why I keep going. It’s so hard. It’s finally catching up with me like, maybe this ain’t going to happen. So, I have branched out into other things, while still kind of trying. I don’t know, man. It’s just all really confusing.

You can’t give up on it. Listen, I was a senior in high school when, “Am I Dreaming” came out, if someone would have told me I would be speaking to you on the phone doing an interview at any point in my life I would have called them a liar. So, keep pushing, bro.

Jason Little: (Laughing) Right! You’re right, man. And it’s a big conversation about R&B with a lot of people. Troy Taylor is doing a lot of stuff with men in R&B and trying to bring it back. You got Diddy talking about it, Tank was having the conversation on his Instagram with a lot of people about R&B. There is a lot of talk about R&B which is good. I ain’t hatin’ on the younger cats, we need all of that, but I wish there was more balance for Urban ac [adult contemporary] artist is what they call us. Putting us in that box hurt us because it’s all about the young artist and the mainstream. I always felt like one of the reasons R&B couldn’t compete with hip-hop is because hip-hop is about “we” and R&B is about “me.” R&B artist don’t work together, but in rap, they work together a lot more than R&B artist.

What do you have going on right now that we can keep an eye out for?

Jason Little: I’m going to release a single. I was trying to get a feature on it, but I’m not sure if that’s going to work out. But I’m thinking some time at the end of the month, I’m going to release a record. Also, I did a fragrance for men. It’s called, “Lucky Man Fresh.” I got that coming and hope to get people’s support on that. The website is www.luckymanfresh.com. It’s already done, but it’s not live yet. It’ll be live soon. The name of the single is called, “In Love.” Tank talked a lot about, “Where the love songs at?” So, I did a joint called, “In Love.” It’s about the money at the end of the day, so securing a feature has been hard. You know how it is, if you’re not that name, it’s really hard to get somebody with a name. They want somebody with a bigger name than theirs. Everyone can give me a follow on social media as well, @iamjasonlittle on Instagram and Twitter and Facebook, Jason Little.

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