Conducting an interview with an artist who is always on the go can present many challenges. When Substream initially attempts to call Hoodie Allen—born Steven Markowitz—over the phone in mid-September, our conversation is marred by poor connection. After several attempts to find better coverage, the phone lights up with a FaceTime Audio call from Hoodie, which comes through with clarity that vastly surpasses the previous attempts to communicate. “That is a trick I picked up on the road,” he tells me. “I don’t know why, but the quality is always better. Feel free to pass that tip along to your readers.”

Hoodie is in the midst of a massive promotional push for his third studio album, The Hype. The album was released at the end of September, and for the past few weeks, the New York native has been putting the finishing touches on the record while also doing as much press as his team can put together. When we chat, less than two weeks before The Hype is set to be released, Hoodie admits the version of the album given to Substream ahead of the conversation is incomplete. “There is another guest verse I need to add. We are getting down to the wire, so I have to [be] done making changes soon.”

The trajectory of Hoodie Allen’s career has already surpassed whatever expectations he or anyone who knows of him may have had. His DIY approach to navigating the music industry was first noticed by the world at large when he received a Best Music on Campus award from MTVU in 2009, but it was his 2010 Pep Rally mixtape that put the marketing and finance major on the map. Featuring samples from a number of leading alternative artists, including Death Cab For Cutie and Ellie Goulding, the release helped Hoodie create a niche entirely his own in an increasingly crowded marketplace. He’s a rapper in the simplest terms, but with a penchant for pop songwriting that helps elevate his music into rarified air where its appeal to the college demographic is hard to quantify.

Where most artists like to tell you how to feel about their music, or at least what they hope you take from it, Hoodie prefers to do the opposite. Before I can ask my first question in full, he turns the tables to ask my opinion of The Hype, which I had heard just days prior. “I like it,” I say. “Tell me why,” he replies. In an attempt to speak intelligently about an album I’ve only heard a few times, I speak to the diversity of the record and how Hoodie’s sound continues to defy whatever barriers people seem to believe it exists within. Where his previous album, Happy Camper, was bursting with potential singles for pop radio, The Hype seems far more personal. Hoodie presses further, but always in a lighthearted way. “I’m just curious,” he tells me. “You never know why people think the way they do.”When my opinion has been discussed, Hoodie begins to open up about the album and how it came together. “I’m very uncertain how people are going to take this record,” he confesses. “I made a lot of songs for this record, so cutting that down to the essential tracks that fit well together and sequencing them took a lot of time. In fact, I think this record took longer to put together than any other release I’ve had so far. Typically, I would start with the songs that are very straightforward pop songs and from there go a bit darker, but this time around I tried to flip that idea on its head a bit. I tried not to do so many of the Hoodie tropes, so to say. I’m not sure what my thought process was behind that, perhaps trying to hook people in a different way, but that’s how it came out. I find it curious that you think Happy Camper was more pop heavy than this. …If everyone feels that way, I’ll be pretty happy, but I know that probably won’t happen.”

I ask if he’s worried that people won’t get what he’s trying to do and Hoodie quickly puts such questions to bed. “I think it’s just how this record is laid out. The next single, ‘Ain’t Ready,’ I think, is going to be a song with legs. Putting that song at track number seven on this record instead of, say, track number three felt like a huge decision for me. Even though it seems most people cherry pick their favorite tracks these days, I still like to sequence an album how I would want to listen to it.

”Our discussion turns to the selection process behind singles for this record, which Hoodie keeps fairly tight-lipped about until another track, “Fakin,” comes up. “I don’t think you’ve even heard the final version of that song yet because no one has, but there is a feature on it.” I admit the version I heard featured no guests, and Hoodie reveals that Washington D.C. native Wale has a verse on the final cut of the song. “That one is special,” he says in reference to the track. “I really like that song, but I felt in order for people to accept it we really needed a guest appearance from an authentic place or else people might dismiss it. Getting Wale on it was just amazing because it not only gives us a break from my voice, but it adds a great punch to the record.

”Hoodie continues discussing the various tracks on the album by telling me about his time with Cisco Adler, who helped create three songs on the record (“Sushi,” “All My Friends,” and “Heartbreak”) during a week-long collaboration early in the recording process. He then focuses on “All My Friends,” which features the band State Champs. “I have had a poppunk type song on every record, but this time, I really wanted to lean into it with a group that really matters to that scene. I sent what Cisco and I did to the band, they dug it, and we fused what the two of us do together to create the final version. Writing the bridge to that song with Derek [DiScanio, vocals] was one of my moments in making this album.”

Hoodie has always put a lot of effort into having each release feel like a complete product, and The Hypeis no exception. “If anything, this album represents my head space over the past year. My goal was for this to be a fun, quick listen that has a lot of replay value. I want each song to work that way as well. For me, I really wanted to take the best parts of everything I’ve done in the past and amplify them. Some songs might feel like outliers at first, but if you listen closely, they contribute to the overall message of the record or fit into the vibe of the album.

”As our conversation begins to wind down, the focus turns to age and longevity in music. Hoodie, who recently turned 29 years old, has spent the last decade of his life becoming established as a leader in the world of independent music. I ask how thinking about the amount of time put into his craft makes him feel and Hoodie confesses he tries not to think too much about getting older. “I definitely didn’t realize I would feel as much like 20 as I do almost at 30,” he tells me. “I really thought I would feel different by now.”

*A version of this interview first ran in the current print issue of Substream Magazine, on stands now and available through our online store!