“Everything is still surreal to me,” says Jeremih. Although it’s been three years since the release of his eponymous debut, the Chicago crooner still grinds like he’s a new artist. In 2009, Jeremih inked a deal with Def Jam after he effortlessly created his first hit, “Birthday Sex.” One year later, he cemented his hitmaking abilities with his infectious single, “Down on Me,” the song that 50 Cent claims saved his career. He kept the momentum going, appearing on tracks for Lloyd Banks, Wale, Diggy Simmons, Meek Mill, and more.

While he records the follow-up to his 2010 sophomore album All About You, the 25-year-old holds fans over with his first mixtape Late Nights, featuring appearances from 2 Chainz, Gucci Mane, Fabolous, Twista, and E-40, plus production from Sak Pase, Soundz, Tricky Stewart, Mike Will Made It, and more.

On the eve of its release, Jeremih phoned up staging-rapup.kinsta.cloud to chat about his latest project, his R&B peers, dream collaborations, and his legacy.

1. When did you know that music was your calling?
I never really knew that I’d be known as an international singer, but I started off playing the keys, and more in particularly the percussions and all types of it, as a shorty growing up. I just kind of put those two things together and focused on how I would come at a lot of records. When I got to my freshman year of college was when I was like, ‘Aight,’ and I started hitting up stages and found my comfort zone. So that was about three years ago and here I am now. Growing up and seeing a lot of people on the road or even being on the same bill and hitting the same stage with people I saw growing up on TV, everything is still a surreal feeling. I feel like right now I’m trying to live in their steps, or at least make my own.

2. Persistence is very important in this industry. A lot of people said “Birthday Sex” would be your only hit and then you topped yourself with “Down on Me.” Do you feel like you have to keep proving yourself?
At the end of the day, I feel like when I released “Birthday Sex,” I knew what it was when we wrote and recorded it and even performed it, I saw how huge that record was going to be. As long as I keep going harder and harder and coming up with what I feel, then I’m hoping the world can feel that too. And that’s what happened with “Down on Me,” because I didn’t even know 50 Cent was going to get on that but big ups to him, he made that a movie. It sold almost 3 million now as far as singles. So I just want to keep going harder.

3. In the past year, you’ve appeared on Wale’s “That Way,” Diggy’s “Do It Like You,” and most recently Meek Mill and Drake’s “Amen.” How do you go about deciding who to work with?
Coming from a production side, if I feel the track personally or if I feel the beat, it’s a no-brainer. You just got to do whatever will fit a hot-ass beat. So for all those records, every situation was kind of different, but we all just went in. Big shout out to Meek Mill, Wale, and Diggy because all of those were three different types of situations. I just heard the track originally and it just started from there. You never really know what’s going to be big or not or what people are going to feel at the time, because every song has a season and it’s about the perfect timing. I just go in there with an open mind—just try to have fun with it.

4. What should fans expect from your mixtape Late Nights?
You can expect the best of me in the last few months. We got some features on there with Gucci, 2 Chainz, Twista, YG, E-40, and Fabolous, just to name a few. These are the kinds of records I’ve accumulated while being on the road. I had to adjust to doing things in places that I probably wouldn’t be as comfortable recording and those records were just that, a lot of late nights. I was able to knock out these records and also get to meet these artists at the same time. We got together and just made it happen.

5. What inspired you to make the mixtape and how far along are you on your third album?
Since I’ve been signed, it’s been three years now and I’ve released two bodies of work through Def Jam and both of them I felt were complete solid bodies of work. This game is so cryptic and crazy now that singles are really what’s popular. Before I even release a third album and have fans purchase something from me, I just felt like I want to give out a free body of work. This is the first mixtape that I’ve ever done in my life. So I treated it like my first two albums as far as the creation and taking my time. I’m tired of hearing a lot of weak songs that I see win and I’m like, ‘Hey, how did that win?’ I’m not even trying to be a hater, I’m just being real. In order for people to hopefully hear me a little bit more, I just had to put more than just my two albums out and why not for free? I put out [Late Nights] knowing it’s a semi-album and I just wanted to put it out because I got other records that I know for sure I want to put on my [third] album that are done, at least over half of it.

6. 50 Cent and Ludacris were the only features on your sophomore album. Will your third be laced with more collaborations?
I can’t say it’s going to be feature-filled, but I definitely will have a couple. There are a few records that I know for sure right now. But not nearly as much as the mixtape. It should be dope. I’m looking forward to it.

7. Which three artists would be a dream collaboration for you?
I’d love to do some work with Missy Elliott. I’d love to just do a joint with Jay-Z. If I could hop on a Hov and Kanye [West] record—if they’re working on another Watch the Throne—that would be the ultimate, of course. And let me see… Alicia Keys!

8. How do you feel about your R&B peers—namely Miguel, Trey Songz, Chris Brown, and Frank Ocean?
I think we are living in a generation of a lot of talented and different artists, especially in this R&B world. I think with Chris Brown, he’s in somewhat of a realm where he does what he does; he’s definitely more than just a singing talent. I definitely feel like we are in a good state of R&B with all of us around right now and hopefully we’ll be in a great state of R&B for the next decade to come.

9. What do you find most attractive about the opposite sex?
I love a woman that just has confidence. It’s probably the most attractive thing on a woman outside of charisma, but you can just tell that off top. But to see one that confident, I think that’s sexy, I think it’s attractive.

10. After it’s all said and done, what do you want people to remember most about you?
To be honest, I feel like all my music is just a lot of different feelings… [I want] people who have heard all of my music and even my Late Nights mixtape, to be able to appreciate that. I want them to hear my records and feel them. [I want them to hear] that feeling and what those feelings sound like. I’d love for the people to remember me overall as the greatest.

–Whitney J. McDonald