We caught up with Ryan Toby from the group City High recently for an interview on Instagram Live. During our conversation, we touched on the origins of his music career, working at A Touch of Jazz, getting into the group City High, writing hits for other artists, his solo music, and much more.


YouKnowIGotSoul: Take us back to working with Will Smith early on in your career.

Ryan Toby: I worked on his “Big Willie Style” album. That was about 1997 or 1998. That was about 5 years after Sister Act II came out. I was actually in a pretty low spot in my life. Contrary to popular belief, Sister Act II was considered a box office flop compared to the first one. The difference is, Sister Act II gained a cult following as it started playing on TV. It was five years after the movie, I was in a tricky spot in my life, I didn’t have any big acting things going on, I was trying to get a record deal, I was having a hard time. I was signed to Jazzy Jeff’s A Touch of Jazz production company in Philly. I was working on my album back then and singing and rapping on my songs, and I couldn’t get a record deal because of that. Record companies were afraid to sign an artist that could sing and rap. Back then it wasn’t the cool thing to do. They wanted me to pick a lane, they thought it was confusing. Now every rapper can do both. I had all these songs and Will Smith had just finished the Men in Black movie. That was a huge hit. He had success with the “Men in Black” song for the soundtrack. So he came to the studio to do a comeback album, because Jazzy Jeff was his best friend. Jeff played him my stuff, because it had rapping. He heard some of my songs and asked who it was rapping. Then the chorus came on and I’d sing the hook, and they told him it was the same kid. He immediately fell in love with my sound and wanted to record a couple of the songs that I had for my project. Jeff called me, told me he wanted to do them, and we got in the studio and hit it off right away. He’s a great guy. We recorded some songs and he liked the chemistry we had, so he asked me to write another one. We did another one there on the spot, and then after that, Will asked me to come work with him in L.A. that night! That was my first introduction into private jet life. Just getting on a plane and leaving when you want. We did some work in L.A. and did some work in New York with The Trackmasters Tone & Poke. That’s where we did the song “Welcome to Miami”. That album went on to sell 22 million copies, it was a big success for me.

Honestly that whole album could have been hit or miss. At that stage in his career, he had finished being The Fresh Prince of Bel-Air and started to become the big time movie star. Then he wanted to do an album, and it was kinda during the Puff Daddy, Jay-Z and Wu-Tang era. So the way it all worked with “Getting Jiggy Wit It”, it all could have been considered corny, but thank God they weren’t.


YouKnowIGotSoul: Jazzy Jazz had you along with many other great artists in his camp. Take us back to the A Touch of Jazz era.

Ryan Toby: That was late 90’s on 444 North 3rd Street, studio 444. That was college. I actually dropped out of college to come and work with Jeff. I had graduated high school and went down to Grambling to try to go to college, because that’s what you’re supposed to do! After one semester, I quickly found out it wasn’t for me. Dre & Vidal were sending me beats and tracks. They told me I should be up there with them. The funny thing is, I was in Grambling, and my major was in business, they didn’t have any music business courses. So I decided to just go and be in the music business. I packed my stuff and moved back to Jersey. I was at Jeff’s studio every day for the next 2 or 3 years. Just learning so much about recording and developing your sound and writing with Carvin & Ivan. A young Jill Scott was in and out. A young Musiq Soulchild was in and out, same with Glenn Lewis & Floetry. We were all kids at that time, and Jeff opened his doors and allowed us to hone our craft.


YouKnowIGotSoul: When the Neo-Soul sound came out around that time, did you get it at first?

Ryan Toby: I thought it was dope. I think one of the first Neo-Soul artists was D’Angelo. When he did “Brown Sugar”, it was a wrap. He was a fly hook looking dude with the corn rows and playing on the piano sounding like Smokey Robinson and Prince. Mind blowing. Erykah Badu came out, it was phenomenal. Even Sade in the beginning. We were on it right away.


YouKnowIGotSoul: You were able to develop a chemistry with Dre & Vidal. What clicked for you guys as a trio to make it work?

Ryan Toby: I was signed there as an artist to his production company. The goal was for me to record my album and then Jeff and his team would then secure me a record deal. I would come down there some days and work with just Vidal, or Carvin, or Keith and Ivan. We were all just there. For whatever reason, it was something about getting together with Dre & Vidal, it was a certain bop we’d create. We were the little brothers down there, the young guys. We just clicked on being the young goofy ones.


YouKnowIGotSoul: So how did you get involved in City High as part of the group?

Ryan Toby: The way City High came about. I was working with Jazzy Jeff, and we finished Will Smith’s album. Everything went back to normal, Will went back to L.A. It was towards the end of the year, November 1998. Around that time, it was the 4th quarter in the music business, and normally the music business shuts down, they don’t sign any new acts. They don’t open up any new budgets until the top of the year. I couldn’t get a record deal. It was like what now? I ran into an old manager, Marvin Thompson. We hadn’t seen each other since I did Sister Act II. He asked what I was working on. He told me he was working with a young kid named Robbie who went to my high school. He was actually two years younger than me. I remembered him from high school. Wyclef had just signed him, and he had a new label with his cousin Jerry Wonda called Booga Basement on Interscope. He asked me to come do some writing for his project. We linked up, I started writing with him and doing collaborations for his solo project. One day, I went to the studio with him, he had to do vocals on “My Love is Your Love” for Whitney Houston. When Wyclef came into the studio, he went crazy because he remembered me from Sister Act II with Lauryn Hill. All of the dots connected. He told me to go into the booth and do vocals on the Whitney song. He asked what I was up to. The Will Smith album hadn’t even come out, so we didn’t know if it was going to blow up or it was a waste of time. Wyclef told me about his label and said I had a chemistry with Robbie and told me to join the team. My contract with Jazzy Jeff was up, so I wasn’t signed, and I needed the money. He thought we could be the new young K-Ci & JoJo. So City High started as a duo. Claudette was just featuring on some of our hooks, that’s why she’s just on the chorus of “What Would You Do”. Wyclef and Jerry and them heard her voice and went crazy and fell in love with her. She had to be in the group. So we went from the new K-Ci & JoJo to the new Fugees. Then we started recording the album.


YouKnowIGotSoul: Talk about the recording of the City High album.

Ryan Toby: To be honest, I was in this place creatively during the Neo-Soul era of hearing a lot of love songs. I wanted write about the dark side of love, the other side, when things go wrong. The concepts were dark. The contrast was like dark concept with happy music. Like “What Would You Do?” is upbeat and happy, but it’s the saddest story ever! It was me trying to be different and wanting to set apart from what everybody else on the radio was doing.


YouKnowIGotSoul: There was so much talent and potential in City High. When you look back at the group, how do you view it?

Ryan Toby: We were the Black Eyed Peas before the Black Eyed Peas got Fergie. We even went on tour with them. It was Wyclef, De La Soul, and Black Eyed Peas. This was when they were backpack rappers and dancers. We were developing this pop edgy sound way before them. It’s so funny because we even had the song “City High Anthem” and signed to the same label. Jimmy Iovine is a very smart man. When City High went bust, he looked at his next best thing. He threw a pretty girl in their group and all of the sudden they had “Where is the Love?” and all of the sudden their whole sound just shifted. They went from underground to super Pop.


YouKnowIGotSoul: After the City High album came out and didn’t do as well commercial as you had hoped, you started writing for other artists. Before there, was there plans for a second City High album?

Ryan Toby: Yea, the album went Gold and just shy of Platinum. We did really well. We had a #1 single. We were nominated for a Grammy and lost to Destiny’s Child. The group was fine and we were excited to do a second album and did start recording a lot of songs. We did a second album, it wasn’t as good as the first album, it was a little rushed. There was some turmoil in the group, the vibe and chemistry was off. We decided to walk away.


YouKnowIGotSoul: Talk about how you moved on after the group didn’t work out.

Ryan Toby: I remember getting a call from Andre Harris around the time when the group was on its last legs, and I hadn’t talked to him since I left A Touch of Jazz. Some years had gone by and I got a call from him and we caught up. At that point, Dre & Vidal had left as well. They told me they had a new studio and they wanted me to come stay with them, and create like we used to. I went down to Philly and I stayed at his house for about a week. We started working on some ideas. The first idea that we came up with after all of those years of not seeing each other, was “Superstar” that ended up on Usher’s album. I remember recording the reference on an 8 track digital recorder in his loft. All of the riffs you hear Usher do, he copied me line for line. Dre thought it would be dope for Usher. He told me they had a great relationship with L.A. Reid so he sent it to him. I went back home to Miami, and I got a call a week later, Dre told me they loved “Superstar” for Usher, and they were flying us to Atlanta to record it with him. That was the first song we recorded with Usher that ended up on his “Confessions” album. We did five songs and three ended up on the album.


YouKnowIGotSoul: It’s crazy how you have Faith Evans on the chorus of that song!

Ryan Toby: Yea, Faith has known Usher since he was super young. They used to record with Puff Daddy back in the day. She was just at the studio one day, working in another room. We just chopped it up and asked her to sing on the record. She went in the booth and one take did it.


YouKnowIGotSoul: You created a single for that album which was “Caught Up”. You also had the song “Follow Me”.

Ryan Toby: We actually created “Follow Me” for Mario, and he recorded it. But Mario’s team at the time weren’t feeling it. Mario loved it, but his team wasn’t feeling it. We turned around and played my reference version for Usher and he loved it.


YouKnowIGotSoul: How did you re-emerge as a solo artist?

Ryan Toby: After that, I was just writing for anybody. Mary J. Blige, Justin Bieber, Chris Brown, Ginuwine, Tyrese, LL Cool J, Lionel Richie, 112. That went on for years and years. Fast forward to now, I’m just in a place in my life where I’m almost 29 years in the game professionally. Like anybody, after 30 years on a certain job, what else is there? I wanted to give myself a new challenge and go back to square one. I had checked everything off my bucket list except the solo project that I started out wanting to do. I told myself I had to do it. My “Songs for the Lockdown” series is really for me. It’s me going back to being that young 14 year old kid that wanted to stand on stage by himself and sing his songs and make his videos and be that fly R&B kid. It’s just something I had to go back to.