Taylor Bennett is just happy to be here. It’s a relatively chilly New York day, and the Midwest-bred rapper is outside posing for pictures as indifferent Fifth Avenue passersby float in and out of the frame. The cigarette he was about to light—someone in his jovial five-person posse advised against it because it's a bad look for the kids—is tucked away and out of sight. With the exception of his Sprayground backpack and the varsity jacket he just shoved the cig into, he’s Chicago’d out from head to toe, from his Bulls jersey to his boldly labeled sweatpants to his Hyde Park-influenced Chicago Leaders fitted.

In fact, Taylor doesn’t even feel the need to button up the letterman because it’s still warmer than his native Windy City, where he just departed from a few hours ago to come here for the first time. Primarily, he's in town to watch his very famous older brother make history as the first independent artist to play Saturday Night Live. But besides that, he's here on his first New York press day, determined to build up and solidify his own fan base off the strength of his then-forthcoming debut album, Broad Shoulders.

“We know that there's a generic kind of music out there," Taylor says from the warmth of the VIBE office a few moments prior. "We know that there's pop music. We know that there's these things that all of these people are listening to, and they haven't really gotten to see a fraction of what we can do in terms of work.”

VIBE/ Christine Imarenezor

Taylor’s confidence in the project is palpable, mostly due to the creative synergy that exists between himself and his right-hand man, producer Ludlow. He worked intimately with Ludlow for an entire year—even braving snow day sessions where the crew literally couldn’t leave the studio—to craft Broad Shoulders, a nod to one of the Chi's many nicknames. It’s a far cry from some of hip-hop’s current gun toting, lean sipping and pill popping offerings. Instead, the tight tracklist reflects the scattered thoughts expected to bounce around a recent high school graduate’s mind. There’s the focus of optimism and gratefulness on the sunny and even-tempered “Smile.” Figuring out mimosa-sipping girls over zealous saxophones and drums on “Favorite Drink.” “H.Y.B.L. (How You Been Lately),” the only featureless song, finds footing in the aftermath of a relationship over pensive keyboard chords. “Every producer likes to make a sound that sounds like what's there, and for some reason I can't do that,” Ludlow says with a laugh. “I've been trying my whole life to make music that sounded like everybody else's and it's not working.”

This idea speaks the loudest on the album’s gem, “Dancing In The Rain,” a moody and melodic number that calls for being carefree, letting worries go and breaking personal guards down. Here, Taylor flexes his own singing voice alongside Shay Lewis, Brandon Fox and the jazzy horns of the Social Experiment's Donnie Trumpet. A majority of the sample-free tracks skew on the positive side, feel-good vibes accurately and effectively conveying the attitudes Tay plans to spread beyond the borderlines of his city. “I prided will.i.am from The Black Eyed Peas because he makes feel-good music," he says, "and that sells in times when people just wanna turn the TV on and not look outside. That's the world that me and Ludlow have been growing in."

To help him bring his vision full circle, a slew of guests from across the board lend their voices on the Freshman Year: 1st Semester EP follow-up. That means everyone from up-and-comers Jordan Bratton, MAX, Talia Stewart and Shay Lewis to hometown homies King Louie, Brill, Simone Bisous, Joey Purp, Donnie Trumpet and, of course, his big bro Chance The Rapper, who blesses the project's kicker and title track. “[Ludlow] made a lot of these artists sound clean," Taylor says. "People tell me, 'I heard that "Broad Shoulders" track, and I've never heard Chance rap like that.’ And I'm like, no, you've heard him rap like that, but you've never heard it mixed like that.”

In essence, Taylor's main goal was to pull the artists out of the comfort zones while curating a soundtrack for something bigger than themselves. “Isn't so much about me, but it's just about growth, the world, life, change and development,” he says. “That's something anyone can relate to, whether it's a five-year-old kid turning six on his birthday or a 70-year-old man on his death bed.”

More often than not, Taylor slips up and calls Ludlow by his government name, Ian, a testament of how much their musical relationship favors a brotherhood rather than a business partnership. However, this bromance is nothing like the real deal. To no one's surprise, the similarities between Taylor Bennett and Chance The Rapper are there because, brotherhood. The affinity for rich instrumentals and hyper melodic backdrops to splatter with stanzas leaning on the poetic side. The slightly deeper, but still cartoony, borderline nasally voice. Overarching positive themes and messages. The face. There's a chance they will always be there. But what can you expect from someone who was Chancelor Bennett's literal shadow for 19 years?

Back when Taylor first started doing press runs, “Chance The Rapper” would pop up in conversation like clockwork. And it’s to be expected, because not only is Chance blazing the trail with his indie hustle, but he and Taylor have “the same face and a little bit of the same voice.” Admittedly, the short-lived annoyance was there on Taylor's part, but it was eclipsed by a brotherly love that shines as brightly as the Bennett smiles combined. When I ask the question today, about the prospect of never shaking the name drop, Taylor barely flinches.

“I realized eventually after seeing all the great things and all the doors that Chance is opening, that the comparison, the fact that my music can be compared to Chance The Rapper's music, is an honor," he says softly. "I believe that Chance is one of the greatest artists out here.”

An idle scroll session down Taylor’s Instagram will reveal that his feed is densely littered with side-by-side pics with himself and his globally buzzing big bro. He's unbothered by the common reference, but more importantly, he won't be held back by it. It's all good when you know your worth.

"It's a double-edged sword, but at the end of the day, you find out that people like Janet Jackson because she led the way for artists who have older siblings or siblings who have been in the music industry before," he says. "If you've got the talent, it's there.”

VIBE/ Christine Imarenezor