The Melodic New Sound of Chicago Street Rap

In the wake of drill’s worldwide explosion, rappers like Calboy, El Hitta, and Polo G are mixing melody and emotion to create music fans everywhere can relate to.
147Calboy Polo G and El Hitta
147Calboy (photo by Toine), Polo G (photo by LVTRKevin), and El Hitta

On a late summer day in September 2018, dozens of young Chicagoans gathered in the woods of South Holland, Illinois to get a glimpse of the future. The event was Camp Smokey Bear, an outdoor, summer camp-themed festival where the city’s best and brightest new talent was performing. Some of the most influential figures in the city’s hip-hop scene were also there, including 26-year-old Finesse Fest, a locally-known DJ and event producer. Already scheduled to play as part of the event’s line-up of DJs, Finesse Fest found out he would be doing double duty that day when he got a call from Calumet City, Ill. rapper 147Calboy’s management team. They needed Finesse Fest to DJ for the 19-year-old rising star during his set. While hastily preparing for the performance, Finesse Fest perused the set list and listened to the corresponding tracks Calboy’s management team had sent. One song grabbed his attention immediately—Calboy’s soon-to-be viral hit “Envy Me.” Finesse was already familiar with Calboy’s sing-rap flow but this song was special. Not only had Calboy improved his melodic delivery and descriptive storytelling, but the track’s somber piano-driven beat felt like the perfect accompaniment for his emotive vocals. “As soon as I played ‘Envy Me’ I was grabbed by how relatable it was,” Finesse Fest says. In short time he saw the song become a phenomenon in Chicago and then across the country. “Three months later [and] it’s on the radio, playing out of cars, and even Meek Mill is talking about it, it was everywhere.”

Earlier that summer in August, 147Calboy, dropped the music video for “Envy Me” on director and photographer Toinne’s YouTube page—a hyperlocal hub for much of Chicago’s budding rap talent. The low budget video would propel the melody-driven Chicago scene on a path to gaining national attention. Calboy’s breakout hit embodied all of the essential elements of Chi Town’s next wave: brooding sing-rap vocals, melodramatic piano-based beats, and lyrics inspired by pain—altogether a sound steeped in struggle. “It’s a story of Chicago’s youth,” Finesse Fest says of “Envy Me.” “It’s about overcoming the poverty, the drugs, the gang violence, and somehow being able to feed your family and friends.”

Despite the song’s heavy subject matter and its specific connection to the experience of Chicago’s black youth, its catchiness made it a new favorite of performative dance and lip-syncing social media platforms like TikTok, Dubsmash, and Triller. In the fall, its YouTube view count exploded and has been steadily gaining exposure since (it’s at 35 million views at the time of this writing). The song could no longer be considered a local or online sensation, it was a bona fide hit charting at 41 on the Billboard Hot 100. The popularity of “Envy Me” opened the door for similar artists like Polo G, El Hitta, and Lil Zay Osama making this wave the city’s most impactful mainstream rap movement since Chief Keef and drill became the talk of social media in 2012. But this new wave is poised to build on foundations its drill predecessors laid.

Chicago drill peaked on the charts with songs like Chief Keef’s “Love Sosa” and “I Don’t Like” nearly seven years ago, but its stars, like 26-year-old Lil Durk, still have a heavy presence in the city. During drill’s early years, the scene wasn’t necessarily absent of melody but Durk, through an airy and bright Auto-Tuned singing voice, pushed the subgenre’s vocal styles into new territory. “Back then everyone was like ‘Man, why you doing that singing shit?’” Durk recalls. “But I wasn’t really focused on drill, I listen back now and can’t believe I made that.” Signed to Def Jam at the time, Durk’s refusal to conform to using the standard drill delivery confused label execs, but it resonated with Chicago’s younger generation. “People sometimes overlook Durk because he’s still so young,” says Finesse Fest. “[But] not only is he from the streets and made it, but he can connect with them in a way nobody else can.” Like Young Chop to Polo G and Lil Bibby to Juice WRLD, Durk became a big brother figure in the city and subsequently, his melody became a source of inspiration.

Vocally, Lil Durk is the current scene’s melodic forebear but the trend of piano-driven beats can, at least in part, be attributed to producer D. Brooks Exclusive. The prolific veteran Chicago producer, known for producing Youngboy Never Broke Again’s “Untouchable,” has worked with artists in the up-and-coming scene like Calboy. The specific piano instrumentation that drill music popularized in Chicago was more akin to a horror movie soundtrack than the sad, atmospheric gloom heard in the current crop of artists' music.

Twenty-year-old North Side rapper Polo G is one such artist. The melodramatic keys on his breakout “Finer Things” are soft enough for a Hayao Miyazaki soundtrack and his naturally smoky melody effectively conveys his pain. His stylistic choice was calculated, as Polo G says, “The melody makes it way easier to connect and show emotion.”

After garnering his first 100,000 plays on a song with no accompanying video with “Finer Things”—a feat in the video-driven world of viral rap—Polo G abandoned the drill-influenced flow he used on his earlier single “Gang With Me” and followed up “Finer Things,” his breakout hit, with the similarly emotional “Hollywood.” On “Finer Things,” he sings about the death he’s had to face in The Chi (“Yeah my friends died too, I know the feeling”) and the nights he has spent in a jail cell (“Almost went insane, went insane, went insane, from all this pain, all this pain, all this pain”). According to Lil Durk that type of emoting has helped this new generation of artist reach audiences beyond the city. “When we was making shoot-’em-up bang music it was for us, but the pain in his [Polo G] music is universal.”

The West Side’s El Hitta has similarly channeled his pain into against-the-odds inspiration. When the 23-year-old sings it sounds like the start of an uplifting hymn made for singing along to; those soul-stirring vocals are often paired with rousing piano instrumentals to create the triumphant effect we hear on his signature song, “Aww Yea.” His animated persona and unique dance moves have set him apart from his peers, with a style he attributes to his native West Side neighborhood where, he says, “We known for footwork.”

Like a 2.0 version of the drill scene, Chicago’s new generation is as digital as it is from the streets, expanding its reach through YouTube and social media. In 2012, Keef and G Herbo used local channels like DGaines1234 and Homespun Media Group to become the talk of hip-hop and more channels like Laka Films, Diamond Visuals, and J Visuals have sprung up to give platforms to the burgeoning scene. And as social media has grown to include dance-oriented video services like TikTok and Triller, artists are using these tools to spread awareness about their music. Artists like Calboy, Polo G, and El Hitta are benefitting from a music industry that is now better equipped to quantify and reward viral success. When Keef first emerged the industry had yet to adjust to the new methods of music consumption, and wouldn’t include YouTube hits in the Billboard discussion until February 2013.

Now, this new Chicago wave has a near-perfect recipe for a sustainable scene: breakout stars, relatable content, a music industry capable of measuring its reach, and the mentorship and inspiration of the previous generation. Polo G puts it all in perspective, “It’s a tale of two eras,” he says. “Chicago reached a peak, and everyone was waiting for what’s next to emerge and then, out of the blue, we showed up.” But, of course, like all new scenes, the music will continue to evolve. And even if these artists evolve past the sound that has become associated with their generation, that struggle and pain of Chicago will continue to be integral to their music. “A lot of these guys coming up these days ain’t been through that struggle,” says El Hitta. “Listen to their raps, their voice, how they speak, they ain’t been through that struggle. But in Chicago, we been through that struggle and we just telling our stories, that’s all.”