After earning their way onto our 2019 Chicago Artists to Watch feature in January, Blake Saint David’s musical output this year was nothing short of impressive. Complemented by a series of very solid singles, the centerpiece of their 2019 works was undoubtedly the album released in April, entitled Cairo, Illinois. From the opening seconds, Blake begins to pour out their heart. In the process, letting listeners in on the tough realities of issues with their parents, their significant other and friends. However, what unfolds is far from a sob story. Blake bears a tremendous confidence - at times it’s emotional, like a teary-eyed fighter throwing dazzling combinations - other times it shows itself in aspirational & explorative ways. Sonically the album is simply out of this world, I can’t recall a young artist from the city who has been able to move so fluidly through sound that it becomes beyond categorization. Cairo, Illinois is deeply dark moments, beautifully bright pop sensibilities and incredible uses of autotune & synths. If I had to peg an album on this list that deserves more conversation around it, this would be it. Put your money on Blake Saint David, they’ll pay you back when he’s famous. - Eric Montanez

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When Chance released Coloring Book, his jump to superstardom came with best-selling hats, headlining gigs at music festivals and three Grammys. But the nature of celebrity also brings extreme trade-offs. Suddenly, Chance’s life became public domain and gave way for harsher criticism. Conversations and their surrounding narratives began to take on lives of their own, from his status as an independent artist, the presence of God in his music as well as how he should address troubling allegations surrounding past collaborators. And yet, through it all, Chance kept himself relatively quiet on these matters. It wasn’t until last summer, with “I Might Need Security” and “65th & Ingleside,” that Chance began to attempt to regain some control of his narrative. The Big Day, inspired by his wedding, continues that reclamation. The album does feel bloated and a bit uneven. But at the expense of clout and some really funny memes, people seem to bypass the fact that Chance is still one of the most lyrically gifted emcees with an incredible ensemble of producers at his disposal. Above it all, The Big Day is a very good album. Songs like “Big Fish,” “Sun Comes Down” and “Zanies & Fools” are the realization of what the best version of this album could sound like: focused with vivid imagery and poignant bars. “Ballin Flossin,” “Let’s Go On The Run” and “Get A Bag” are dance hits hard to shake off once you hit play. Marriage can be a flex, it just needs to be approached with care and allow for intimacy to flourish. If that’s the big theme here, it needed a little bit more of both. - Pedro Gonzalez

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With a punky surf rock sound, Chicago trio Dehd brought a casual attitude into recording their latest album Water (their first since 2016 with an EP and badass singles in between). Comprised of three musicians battled-tested from the independent scene, Jason Bella (NE-Hi, Earring), Emily Kempf (Vail, Lala Lala) and drummer Eric McCrady deliver seemingly effortless sound that proves just fucking doing it is the right thing to do. It feels nostalgic but also extremely optimistic for what rock and roll can be. My favorite part is that as I listen to this album I can be trudging through the snow or basking in the sun —soaring aerial vocals, fearless drumming and delightfully simple guitar is the genuine magic I didn't know I was looking for. - Patrick Welby

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Chicago is fortunate enough to be the home of the psychedelic-rock band, Divino Niño. In June, Divino Niño released their debut album, Foam. The romantic piece takes us on a tropical and soothing journey through the use of their bilingual lyrics and celestial melodies. Singing in English and Spanish is becoming a highly praised characteristic and the band nails it. The group successfully distinguish their soulful sound with the help of their deeply rooted Pan-American cultures. Foam is a vibe that blends '60s-inspired psychedelia and futuristic sounds that can be heard through all Latinx generations. Beginning with "Foam," "Quiero," and "Coca Cola," the band switches from both languages to illustrate an endearing love story along with implementing jubilant melodies and woozy instrumentals. While the image of an everlasting bond is still present throughout the album, the lyrics turn cloudy with "Plastic Love," "Flamingo," and "Maria." As the project proceeds with "Melty Caramelo," "B@d Luck," "Koda," and "Cosmic Flower," the lyrics become more vulnerable and unapologetic regarding the adoration that two people hold. Like in all relationships, there are moments of tenderness and bitterness. Foam is an album that sums up the infinite peculiarities of an amorous relationship. Divino Niño's debut made us experience an "everlasting lucid dream" with their artful execution. - Melissa Ortiz

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Coming from a person who drove a ‘92 Camry most of their young adult life, Femdot’s ‘94 Camry Music slaps differently. While the skits pay special attention to using all the weird noises those older Camry models made, ‘94 Camry Music depicts exactly what an old car gives someone: memories and unpredictable adventures. Femdot’s storytelling and songwriting are on top display here. These skits are eloquently placed between tracks and make for a great ride down memory lane and into Femdot’s past life. This is depicted perfectly on “Snuck to Matty’s” en eerie retelling of a party that ended in a fatal fight. This type of experience with Femdot’s music has been there from the beginning, but this project takes a giant leap forward in technique and placement. - Luis Hernandez

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From opening 2019 with Tomorrow Never Knows, a sold-out record release show in March, a litany of shows that spanned both the Chicagoland area and the Midwest college circuit, and crescendoing with a pair of sold-out shows at Lincoln Hall (ironically with Charly Bliss, who the band played with back in January as part of TNK), to call the year great for the indie-pop darlings is a vast understatement. This is mostly a testament to how incredible their debut album, For Now, is. The local Chicago indie-pop/rock scene has been bubbling and growing in recent years, and I truly think For Now is emblematic of the scene’s best parts. While the album is a collection of uplifting songs teeming with energy and youth, album standouts “Ride,” “Wish You Were Right,” “Just Kids,” and the titular “For Now” illustrate exactly why For Now is one of our albums of the year. Leading up to For Now’s release, Patino summarized the album by telling us, “For Now [...] is about everything being temporary, but just because things are temporary doesn’t mean they lose their value in terms of what we learn from it.” Girl K has proven over the year that there is nothing temporary about their meteoric rise, and the best is yet to come in 2020 and beyond. - Geoff Henao

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Legacy! Legacy!, Jamila Woods’ second album, is a complex, empowering listen weaved from the lives and works from a dozen authors and artists of color as well as her own. The legacies of those figures provide each track both its inspiration and its title. Woods, a poet, educator, and empath, conducted extensive research for her album. As a result, the tracks are organic revivals and interpretations of the titular characters rather than a stale retelling of their legacies. In “Zora,” Woods builds on the wisdom of novelist and genius Zora Neale Hurston by celebrating the freedom of having a layered, dynamic identity. Later, in “Frida,” Woods considers how Frida Kahlo’s understanding of distance in romantic relationships could function in her own life. On standout “Basquiat,” Woods plays with the anger projected on and felt by black artists, Jean-Michel Basquiat in particular, and how it has affected her. Importantly, Woods uses the legacies not just of people with the broadest impact on society, but also those with the most intense, personal impact on her: her family. In each of her sonically diverse tracks, she draws deeper into her family and her personal life through the lens of these 12 figures to create an album that is incisive and broadly felt. - Mitchell Beadows

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Jean Deaux has proven to be one of the most versatile talents in Chicago time and time again. On last year's KRASH, listeners cruised through nine tracks showing off Deaux's multifaceted skill-set. This year, we observed Deaux helm a more focused creative direction, doubling down on roles as a director (for fellow Chicago artists and her own videos) and musically through her Empathy EP. In 22 minutes, Deaux gives listeners some of her sharpest work, floating effortlessly across each record. She voices her self-reverence on the project's first two tracks, "It's Whatever" and "Higher Me," while guests such as Kehlani ("Anytime") and DuckWRTH ("Life Lines") help explore Deux's encompassing themes. As listeners become engulfed in Deaux's vocal prowess, the picture she's painting seems to unveil a spiraling relationship and the emotional rollercoaster that comes with such an experience. By the time we reach the final track, "Speakerphone (Trust Issues)," Deaux seems to be on the opposite end of the spectrum from where she first started: vulnerable, reflective, and empathetic. - Carlos Castillo

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Kaina has been racking up trophies all of 2019. Sold out headlining shows of her own, sprawling North American tours supporting major acts (Cuco, Sleater-Kinney, Durand Jones to name a few), and becoming a critic's darling. She’s Chicago's sonic sister. Her biggest feat in 2019, however, is her lush debut album Next to The Sun. The album was celebrated here locally in Chicago with a pop-up featuring her Mom's home cooking. Her parents were frequent regulars at hometown shows —often receiving the loudest round of applause. Her band and collaborators are also Chicago's brightest stars. That's the most comforting thing about Kaina and Next to The Sun. It's a family affair. It's warm, natural, familiar and essential. You leave happy and full but always find room to go back snack some more on this delectable piece of Kaina's heart and soul. - Patrick Welby

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The duality of man is Carl Jung’s concept that the human mind is divided into two parts —who we are, and who we desire to be. In 2019, perhaps no artist represented this concept better than underground legend LUCKI and the two projects he released this year: Freewave 3 and Days B4 III. The former was the first of the two to drop and it was a dark, nihilistic reveal to his inner turmoil. Paired with grimy, stripped down beats, LUCKI’s lyrics told stories of an overall decadent lifestyle: heartbreak, drug abuse, and strained family ties. The latter, released in late October, is LUCKI reclaiming his triumphs. He still touches on the painful aspects of his reality, but the themes on DB4III are centered on celebrating his come up and doing the dash. FW3’s “Glory Boy” is arguably the most representative track on the project (and my personal pick for song of the year). In less than 2 minutes, LUCKI is blunt with his struggles, showcasing the full extent of the toxicity around him. In just a short 8-bar verse sandwiched between two hooks, he explains to the listener his attempts to use multiple women to fill in the gap left by his ex (“I got loyal hoes, but I need more”), the physical effects of substance abuse (“Perc 30 slurrin’ my speech, uh, I’m itchin’, it got me poutin’”), and the state of limbo he feels between wanting to escape the disingenuous nature of L.A. (“Can’t wait to go back home, sick of bein’ ‘round out-of-towners”) while acknowledging that home is where the hate is at the very end of the song saying “I can’t go back home, n----s want me out my glo.” On the flip side, DB4III’s touchstone can be found in its lead single “4 The Betta.” With its dynamic trap beat, it already sounds different than anything on FW3. Right away, he sounds more confident and braggadocious rapping “In sunny weather, I keep my head up/ I'm in a Ghost, these n----s haters, want me to let up.” It’s a far cry from the emptiness found in FW3. Here, LUCKI is relishing in his wealth and the jealousy of his haters, while still unable to completely shake off the pain of his past. By the end of it all, he asks you “Who do it better than me?” And in a year where he dropped not just two of our top five albums of the year, but two of his best bodies of work in a remarkable catalog, it really begs the question if there really is anyone out there doing it better than Flawless LUCKI. - Alejandro Hernandez

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On Saturn Return, Mother Nature take stock of their relationship with addiction, egos and dreams in search of greatness and spiritual freedom. T.R.U.T.H. and Klevah Knox cover the themes presented here with their own unique steez and keen rapping. There’s a tangible synergy between the two emcees that carries over with the fellow Gr8 Thinkaz members who make contributions to this EP. Enlightened and ruminative, there are several lines across Saturn Return (specifically in “Ritualz” and “Super Natural”) that allow the listener to meditate and shift towards their own growth. - Pedro Gonzalez

* * * *

You Can’t Sit With Us

Pivot Gang

Pivot Gang’s You Can’t Sit With Us is one of the most familiar debut albums I’ve ever listened to. Saba, Joseph, Melo, Fresh, Squeak, Dae Dae, DamDam and John have been working together for years, forging a brotherhood in music and life. Their lives and experiences so very intertwined. Each solo release over the years has built on one another; random loosies, EPs, and projects all introduced fans to this group’s lives in a very real and very relatable way and fans bought in. That's why the passing of Pivot co-founder, John Walt, in 2017 took such a striking toll on the West Side collective and Chicago's arts community as a whole. Yet at the release of You Can’t Sit With Us, with John front-and-center in the album’s artwork, Pivot seems more focused than ever to make their mark and do their part to have John’s legacy live on. A rap group isn’t a new concept. Collectives have been collaborating since the beginning of hip-hop. What makes Pivot Gang stand out is the close bond the group has with one another, and their ability to allow fellow members to live in their space. While you can hear plenty of common themes and overlapping influences throughout You Can’t Sit With Us, each member brings something unique to the table and a style that identifies them individually. Everyone comfortable, everyone being themselves. Plenty of raps to be heard from the home team, but Pivot did invite some guests to the party including extended Pivot family, Smino, Mick Jenkins and Jean Deaux. Adding to the project’s overall importance to the local music community and fans alike. We’ve seen the group come-up from recording in basements to selling out back-to-back shows in Chicago. Better yet, we got to hear it. You Can’t Sit With Us, is their latest entry and a statement record. They’re here to stay. - Brent Butcher

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This year Polo G gave us one of the most moving debut albums in recent memory. On a surface level, Die A Legend is placed in the intersection of life-changing success and a life of traumatic experiences. Navigating through a year that moved about as fast as it possibly could for a 20-year-old, we find an incredibly introspective young artist reflecting on the realities that brought him to this point & the whirlwind of emotions that come with it. And while his talent and determination have led him to brighter days, the PTSD remains a challenge. One thing that’s clear throughout the album’s 14 songs is that Polo G is an incredible storyteller. Through descriptive scenes of the day to day, he vividly paints the picture of scenarios unfolding. Often taking things a step further, shedding light onto the mindsets & forces that perpetuate them - from coping mechanisms to cycles of revenge. These skills in their own right would’ve made Die A Legend a worthwhile listen, but he’s also able to do the thing great artists do to elevate their work and made it relatable, not an easy task given extreme realities he’s been faced with. The themes that color so much of these songs —pain, aspirations, sadness, confidence, loyalty, competitiveness, etc.—are ultimately all encompassing human feelings. In an interview with Rob Markham of Genius, Polo further expresses this approach: “I went about it on connecting to everybody on a personal and emotional level, no matter what type of demographic you come up from, you could feel this.” - Eric Montanez

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“Supposedly Cousteau and his cronies invented the idea of putting walkie talkies into the helmet - but we made ours with a special rabbit ear on the top so we can pipe in some music,” explains Steve Zissou (Bill Murray) from The Life Aquatic just as you’re nearing the end of “Billy Blanks” and only beginning to plunge through Qari & greenSLLIME’s Operation Hennessey. Much like the movie its name drew inspiration from, this project is one of a kind. Through seven tracks, the two friends complement each other’s strengths. Qari fluidly maneuvers each song with every bar he drops, captivating listeners just as much as greenSLLIME’s anomalous (and satisfying) production does. “Operation Hennessy,” “Pass the Mic” and the Mick Jenkins-featured “Pony” are standout records that will leave listeners anticipating any potential future records the two might have in the works. As muddy as the mid-February release sounds, Operation Hennessy undoubtedly delivers some of Qari and greenSllime’s most dynamic work. - Carlos Castillo

If you are familiar with Chicago music, you’ve likely heard of Will Miller before. For years, his trumpet and beats have fused themselves into the music of the city’s biggest names, helping to create some of the most lasting projects of the past decade. His dedication to cultivating community and his insistence on the place of fearlessly exploratory jazz in all music is distinct. He is the type of person who makes Chicago music “Chicago.”

Written, produced, and arranged by Miller, Resavoir is the refined release of that powerful, experimental energy which he and so many others have long nurtured. Leading not a band but a community of 18 credited musicians under the same name, Miller put out a project that is shocking in its depth.

In isolation, album standouts like “Taking Flight (feat. Brandee Young)” or “Plantasy” are each impressive. In the former, Brandee Young’s thrilling harp supplements the horn-led melody to create a track that is deeply refreshing and never flat. In “Plantasy,” the keys and trumpet ward off emotionally jarring phrases from the rest of the band to sustain the listener on a soothing, redemptive melody. However, when played in sequence, these tracks become transcendent through a combination of chemistry and freedom, much like any of the musicians composing Resavoir or the Chicago music scene as a whole. - Mitchell Beadows

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Catharsis is known as the release of intense emotion, typically that of fear or pity. It’s a concept that originated from the Ancient Greeks, who believed that by purging these emotions through art, humans could restore happiness in their system. In an era where more and more rappers attempt to evoke emotion through music, we must never forget that few artists can rightfully claim to be pioneers in the same vein as Supa Bwe, and even fewer can claim to have perfected the art of catharsis as he has.

Jaguar is Supa at what could be his most primal, tapping into the deepest depths of human emotion; anger, passion, sadness, and love. These are the themes that he explores on the most intimate levels. By the end, you’ll feel the full spectrum of those feelings, but you’ll also have a sense of tremendous relief. And for those that are willing, listening to this EP while tripping off LSD can turn the listening experience into something otherworldly entirely. - Alejandro Hernandez

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Leading up to 2019, Tobi Lou had blessed his fans with several EPs that showcased his potential and left fans yearning for more. This year we finally got to see him deliver his debut album, Live On Ice. The 21-song project finds Tobi skating all over tracks with some of the best flows and raps of his career. Each bar showcased the true witty creative nature that helped him build his passionate following. For example, in “I was Sad Last Night I’m OK Now” Tobi raps ”I'm on the grind everyday like Pretty Ricky. I want a house by the lake like Ricki, Ricki.” Only Tobi could create a bar that mixes a mid-2000’s R&B group with a 90’s daytime talk show lost in the ether of pop culture. Not only does Live On Ice give you all the intangibles of a fun album, it gives another look into Tobi’s irresistible personality. - Luis Hernandez

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The O'My's Above Ground EP consists of six songs filled with serenity and beachy guitar strums that sway eardrums. Serving as the perfect follow up to last year’s album Tomorrow, the EP starts with "Summer Jam" and "Don't Know Better," which deliver love-filled lyricism, finger-snapping drumming, and trumpets that ascend as the songs continue. "Space Bounce" proved its potential to be a love song and ended with a captivating guitar melody. My personal favorite, "Strawberry," showed the duo's versatility by starting in a sentimental atmosphere and progressing into a blissful beachy vibe. "Mood" - which features Pivot Gang’s FRSH Waters - and "Luke's Song" wrap up the project on a wistful note by including lead singer Maceo Vidal-Haymes’ powerful vocals and the band’s always alluring instrumentation. All in all, Above Ground became one of our favorites of 2019 due to its gratifying sound and succinct delivery. - Melissa Ortiz

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Driven by an insatiable need for constant innovation, 19-year-old Victor Internet found himself at a crossroads in early 2019. As his career started to gain traction he began to feel uncomfortable by the restricting descriptors thrown at him. With the pressure to continue building his fan base while striving to pursue more expansive sounds, Victor set on to create Victor’s Debut. The project is an outline of Victor’s past three years, exhibiting his virtuosity as a singer/songwriter/producer/arranger. The first half eases fans into it with the heartrending, ballad-style records we’ve known him for capped by a delightful secret Spanish refrain attached to “Honest's" backend. Following a quick interlude, Victor breaks through his self-doubt and the box he was being placed into. This is where Victor's Debut gets exciting. “2017” is a braggadocious cut that finds Victor chanting with his chest out “I was talking shit when I had nothing;” “VEINS” turns a disadvantageous situation into a lesson to take risks that feel right; “SOUTHSIDE” gives us a look at what his upbringing was like growing up with jarring detail; and “UNFAIR” closes out the project by posing Victor’s newest challenge: becoming the main provider for his family and filling the void of his absentee father. It's arguably the biggest responsibility he's ever held, but the maturity shown on here makes us feel he'll find his way. - Pedro Gonzalez

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Woah, that was intense! You might not use the word intense to describe Whitney’s vibrant and warm melodies in general, but Forever Turned Around is a lot more personal than the band’s debut Light Upon The Lake. The 7 piece outfit took Chicago and the nation by surprise with its 2016 debut, drenching listeners in nostalgia, summertime vibes and some great horns. The followup however focuses more closely on the relationship of the band’s founders Julien Ehrlich (vocals) and Max Kakacek (guitar).

Whitney dives deep into the struggles that come with personal relationships in their sophomore release. An expression of what are generally private details in a person’s life, Ehrlich draws listeners in with a very relatable theme throughout. Don’t worry though, when the content gets heavy Whitney always counters its effect with the light and airy production we’ve come to know and love; making this summer release safe to listen to on a grey day in December in Chicago.

With the year coming to a close and a new album under their belt, Whitney recently concluded a five night residency at Chicago’s Thalia Hall and announced their 2020 tour plans just last month. Whitney is joined by CHAI beginning in January for the band’s stateside dates, and they hit the UK beginning in May. Whitney sounds great through your speakers, but their presence on the stage is not something to be missed. Listen to one of our favorites of 2019, and catch this ensemble live in the new year. - Brent Butcher

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“Dream Boy”

Beach Bunny

* * * *

“Wait”

Billy Lemos

ft. Still Woozy & Blake Saint David

* * * *

“Chariot”

Calboy

ft. Meek Mill & Lil Durk

* * * *

“Do You Remember”

Chance the Rapper

ft. Death Cab for Cutie

* * * *

“Run”

Deeper

* * * *

“Lucky”

Dehd

* * * *

“Foam”

Divino Niño

* * * *

“Hold On”

DRAMA

* * * *

“TRUDAYYY!”

Elton

* * * *

“Fragile”

Eryn Allen Kane

* * * *

“Happy Break Up Song”

Femdot

* * * *

“Summer is Cancelled”

G Herbo

* * * *

“Häagen Dazs”

Ghetto Sage

* * * *

“No Friends (Remix)”

HappyBirthdayCalin

ft. G Herbo

* * * *

“Popstar”

Intellexual

ft. Liam Kazar & Benny Sings

* * * *

“Pretty Love”

Iris Temple

* * * *

“I Became My Brother”

Jack Larsen

* * * *

“Okay”

Jackie Hayes

* * * *

“BASQUIAT”

Jamila Woods

ft. Saba

* * * *

“Anytime”

Jean Deaux

ft. Kehlani & ROMderful

* * * *

“Hear Me Calling”

Juice WRLD

* * * *

“Green”

KAINA

* * * *

“Voices”

Kembe X

* * * *

“4 The Betta”

LUCKI

* * * *

“These Are The Days”

Neal Francis

* * * *

“High Vibrations”

Melo Makes Music

* * * *

“Flow Seats”

MFnMelo

* * * *

“Gang Member Shit”

Monster Mike

* * * *

“Glowing”

Ness Heads

* * * *

“Song 31”

Noname

ft. Phoelix

* * * *

“Dreams”

Phoelix

* * * *

“Bad Boys”

Pivot Gang

ft. Smino

* * * *

“Diamonds”

Pixel Grip

* * * *

“Pop Out”

Polo G

ft. Lil Tjay

* * * *

“Pony”

Qari & GreenSLLIME

ft. Mick Jenkins

* * * *

“Ratchett”

Queen Key

* * * *

“Plantasy”

Resavoir

* * * *

“Yellowbrick”

Ric Wilson

ft. Jia Lih & Sam Veren

* * * *

“Mi Coche”

Ryen

* * * *

“High”

Slow Pulp

* * * *

“Trina”

Smino

* * * *

“Highly Favored”

SoloSam

* * * *

“Crying in July”

Sports Boyfriend

* * * *

“LOOK”

Supa BWE & Qari

* * * *

“Let Me Go”

Tatiana Hazel

* * * *

“Dipped”

The Cool Kids & Kenny Beats

* * * *

“Ferry Song”

Twin Peaks

* * * *

“Pepsi”

Valee

* * * *

“VEINS”

Victor Internet

* * * *

“Valley (My Love)”

Whitney

* * * *