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From Stiff to Swagger: The Evolution of Jack Harlow’s Music Videos

After three years of steady releases, Jack Harlow finally looks the part of a budding star.
The Evolution of Jack Harlow's Music Videos

Let’s get this clear: I love Jack Harlow. Ever since his “Dark Knight” video was placed before me on ye olde Twitter in 2017, I have been a devoted fan. The young man has flow, charisma, swagger, bars; you name it, he’s got it. His 2018 mixtape, Loose, was my favorite debut of the year, and his feature run following the project always caught my ear. 

Now, with the release of “THRU THE NIGHT,” featuring Bryson Tiller, we are basking in the light of an evolved Jack Harlow. Gone are his glasses, gone are his sweaters, but the New Balances stay. They’re free; he needs you to know.

From stiff performances packed with promise and self-awareness to effortless skating on the rink with a shorty, Jack Harlow’s music videos are the easiest way to track his growth as an artist. He’s a master of visual rhetoric as it applies to get us excited. He’s a master of visual rhetoric as a matter of taking us along for his creative journey. There are apparent chapters to his music videos, and in the spirit of his new drop, we’ll be breaking down those chapters for your viewing pleasure. 


Early Days

“Every Night”

DIY spirit, flat colors, melancholic beat with a nighttime shoot—everything about this video screams “First time,” but it also screams “Passionate.” There’s an attention to detail with “Every Night.” From the shot of the New Balances we love so dearly to the attempts at matching atmosphere with visual representation, we get the sense that Jack Harlow came out the gate trying. Just look at the way the frames cut to the beat of the drums as Jack slips out of the car and onto the street, spitting a little too perfectly on beat, if not simply stiff.

There’s an effort to the persona he’s attempting to pull off, and we can feel it. It’s endearing for the right and wrong reasons. On the one hand, with the video and track, Jack has a clear vision, garnering our respect. His hook game is enthralling; his verses have some admirable wordplay, and the content (generous tips at Applebees) leads us to believe Jack is an honest man; everything feels like a promising work in progress. On the other, there’s an element of force to the visuals—as if someone described what a dark rap video should be to his team and they went for it without a second thought—that keeps us at bay.

We’ve yet to buy into Harlow at the point, but as far as starts go, “Every Night” is a great one. Shout out to the dog he’s walking, too.

“Ice Cream”

We’ve traded in dark aesthetics and acting hard about our outings to chain restaurants for bubbling sample cuts and bright colors. This first point of growth is a welcome transition. Leaning into his physical appearance, Jack Harlow knows who he is—and who he wants to be, at this point—as an artist. Slick talk about women and making it in rap make this an endearing, albeit simple, come-up track, but the borderline silly visuals keep us engaged beyond the standard fare of the writing. “Ice Cream” teaches us that Jack Harlow doesn’t take himself too seriously; he knows how to have fun with it.

The warm color changes, and Jack’s wardrobe sell this video. Roaming through what we assume to be Louisville streets in a makeshift ice cream Sprinter, Jack hangs out the door and raps into the camera with a looser flow. Cut to him dancing on the hood of the van, then cut to him unabashedly dancing at the pool party, and we can’t help but fall in love. He’s having such a good time! From “Every Night” to “Ice Cream,” Harlow found his groove as an artist doing it for the love. There’s nothing self-serious about “Ice Cream,” and as it carries over the clear vision sparked on “Every Night,” we have nothing but respect for the young man who is so evidently secure.

“Ridin’ Round Town”

We’re back to muted colors, a fall, DIY aesthetic, and some creeping keys. The twinkle of the rhythm gives us the impression this is going to be another “Every Night”-esque banger, but already we’re off to a better start. For one, Jack’s done sounding stiff on the beat. He treats us to a handful of sets and scenes, bringing the joy of the “Ice Cream” video and his dancing to each one. There’s a fresh sheen and polish to these visuals. We’re starting to get a budget. We’re starting to spend wisely. “I’m bringing the heat and I’m bringing that passion” he asserts into the camera, and finally, we believe him.

“Ridin’ Round Town” works for many of the same reasons as “Ice Cream.” Jack Harlow knows who he is and what he wants out of his burgeoning career. He wants to be the hometown spitter going pro, and his bubbling ferocity on the mic comes across in the upgrade to his music videos. The cuts are smoother; the shots are tighter; the lighting is flattering; there’s B-roll. Though this song is more serious than “Ice Cream,” featuring Jack experimenting with melody, the color choices, and B-roll shots give “Riding’” the same sense of personality. We’re getting to know Harlow by this point, and it seems like we’re ready for the ride.

“Got Me Thinking”

At this point, it feels as if we are living a tale of two Jack Harlows—and not in a bad way. There’s the gloomy, trappy Jack who wants to go hard and eviscerate the mic with his attractive baritone. Then there’s the poppier, carefree Jack who wants to make music for fun, to catalog his experiences as a kid, and to bolster the art scene in his community. Both Jacks are coming into themselves across these early videos. Much like “Ice Cream,” the ethos of “Got Me Thinking” is Jack Harlow’s self-awareness and aversion to gravity. We being with an open mic, cut to Jack stunting in a field, then cut to the narrative meat of the video.

That’s right, this time around we aren’t just dancing in place. This time around, Jack is experimenting with visual storytelling, using finer details to portray the deeper feelings his pen is slowly working towards. Close-ups of hands held as the narrative anchor, followed by shots capturing a playful intimacy, leave us with the impression this was the most serious treatment Jack had written or received. Of course, there are the break-up song classic shots: frustrated calls dropped, standing outside her door at night, melancholic walking off into the distance. When compared side-by-side with Jack’s previous visual work, nothing about these standard scenes feels trite. We return to the feeling of “Every Night,” of Jack Harlow sincerely trying.

Break Out

“Dark Knight”

This video is the moment Jack Harlow transitioned from hometown rapper to hometown hero. “Dark Knight” marked the moment Jack Harlow would cross over from Louisville to the higher sphere of the internet. It was my formal introduction to the rapper, and what a banging, brooding introduction it was. Gone are the forced days of “Every Night.” Instead, the beginnings of Jack’s potential stardom are on display: His fearsome energy, his comfort in front of the camera, his smooth flows and barking presence. A trappy departure from his otherwise jaunty poetics, “Dark Knight” showcased range, but it also promised us a star.

Closing in on three million views, the aura of “Dark Knight” feels special even over two years on. Each replay of the single reminds us of the spry and boundless energy Harlow brings to the table. The video marks the moment Harlow comes into his brusk voice. Visually, the shadow work and shots racing through the city get our blood pumping. Watching Harlow roll deep with his crew is equal parts cheerful and foreboding. We see he can act hard, and we believe it well enough. “Dark Knight” is the video Jack Harlow hoped would secure him lifelong fans. It worked.

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“Wasted Youth”

Back to brightness and back to timing and cinematic effort, we open on the beat triggering a fountain pulsing to the rhythm of the starting synths. By this point, Jack Harlow’s star has risen—he dropped Gazebo, and a record deal is on the horizon. The colors pop, the budget is obvious, and Jack’s performance is purposeful, smooth, and finally on the eve of effortless. His wardrobe is an extension of the “Ice Cream” video, with more finesse and attention to present fashion. Everything about “Wasted Youth” feels like a culmination of the sunny videos Jack had been releasing up to that point.

“Wasted Youth” works because it feels at times frivolous in the way the summer days of our youth feel silly and inspire us to frolic. The sets are simple; the shots aren’t enrapt in narrative. We’re back to focusing on Jack, but with smoother camera movements and a host of inventive angles. Everything about this video is just better. Where Jack broke out with “Dark Knight,” the sheer production value of “Wasted Youth” lets us know Jack has officially arrived. We get the sense he’s got a real team behind him now, and it’s only up from this point.


The first Loose single and the official note Jack Harlow has broken through, “SUNDOWN” is to “Dark Knight” what Aesop Rock’s “Daylight” is to “Nightlight.” The tale of two Jacks continues but on a pleasant note. The B-roll is intentional; the color palette has evolved from a smattering of vibrancy to thoughtful choices meant to capture the essence of the track and to flatter Harlow. By this point, we’re two years removed from “Every Night,” and we quickly realize a lot of growth can take place over that amount of time. Much like “Dark Knight,” this cut rests on a catching beat and Jack’s superb technical rapping and charisma.

Jamming out of car windows and dancing on roofs, all of Jack’s joy perfectly blends with his desire to appear like a serious rapper. Jack brought his city out to celebrate his success with him, too. We’re no longer looking at him as the goofy kid making rap for fun. Jack’s fun has evolved into fuel to make some of the best music of his career. His happiness and passion are infectious. “Dark Knight” made us fans for life, and “SUNDOWN” is a reminder of why we became fans in the first place.

Loose Era — The Formation of Swagger


We’ve moved on from proving we can rap, proving we belong here, and proving we know how to enjoy ourselves. The Loose era marked the development of Jack Harlow’s voice as an artist: Someone who blends the raps with the melodies in a semi-serious, heartfelt way. The jeer of “Ice Cream,” then, works its way into this video for “PICKYOURPHONEUP,” which is entirely green screen fun. Everything about this video screams voice, from the colors to the breezy dancing. 

The hot purples and neon flourishes sell this video. It’s a new type of fun for Harlow, who usually runs around town, trying to capture the essence of his youthful humanity on camera. The simplicity and variety of the video is appreciated, too, considering how intense his early work appeared by contrast. Also, this video marks the first time Jack Harlow interjects his focused rap persona into his fun-loving rap persona. His long, pouty gazes at the camera tell us everything we need to know: Jack Harlow is here to stay. He’s found himself.


Back to the concept. This time, Jack delivers yet another loose narrative to go with the title and content of the song. Standing in front of a private jet in a full suit and his New Balances on, we get that same fun-meets-focused energy we got on “PICKYOURPHONEUP,” but instead of dancing and staring us down, Jack leans into his monotone delivery and pouty demeanor. For as much budget as the young man has, there are several choices in this video keeping him grounded. The shoes, for one, and also the option of old Pontiac for the car. Indeed, by this point, Jack has the money for a nice rapper’s car, but whipping the Pontiac feels right.

We’ve finally mastered the art of the brooding rap video, too. The colors are nicely icy, with Jack looking and sounding fresh. He’s leaning into the depth of his vocal tone and traded in dancing for minute movements, catching our eye ever-so, but never taking up the whole frame. The video is, to put it, cold. Jack Harlow mastered the art of mean-mugging without coming off as unapproachable. He’s tough, but he’s genuine. He’s got a soft side, but he’s not overly sentimental. As I said, Loose is about finding a voice, and in terms of visual rhetoric, this is what we like to see.


The tour footage video is a classic genre of music video. Instead of featuring a woman and working through the narrative of “SYLVIA,” Jack opted to stitch together footage from the Loose tour and use “SYLVIA” as a backdrop to celebrate his earned success. Packed out rooms and mood lighting make this video a quiet triumph. Watching Jack go from biking alone to rolling with ten friends under an overpass, to commanding a stage is so rewarding. “SYLVIA” doesn’t mark any growth in terms of video conception, but rather, is a showcase of Jack’s career growth. Take “SYLVIA” as advanced behind-the-scenes content. We love to see it.


The last of the Loose era videos, “DRIP DROP” is both an album standout and visual feat for Harlow. The video features a healthy amount of experimentation with effects and lighting, multiple scenes, a cheery disposition, and, goodness, the same amount of blithe fun as we once saw on “Ice Cream.” Jack fancies himself an artist painting a woman, he has scenes just spitting, and he cedes the floor well to CyHi. Really, “DRIP DROP” succeeds because Jack Harlow is finally coming into his rapper swagger while having a good time. Gone is the pout of “CODY BANKS” or the overt brood of “Dark Knight.” Though Jack packs the track with bars, the video is a playful marvel.

“DRIP DROP,” with its assortment of angles and fantastic shadow work, marks the moment Jack Harlow fully forms on the screen. From the patter of the raps to the effortless flow, to the fun-loving visual rhetoric, Jack uses “DRIP DROP” to show us who he is. A creative with the world ahead of him, “DRIP DROP” feels as unique as “Dark Knight,” if only because after a score of videos bouncing back and forth between personas and voices, Jack has finally unified all sides of himself.

Knocking on the Door of Stardom


The glasses are gone. The blurb could end there, but let’s talk about the glasses. The end of Jack’s glasses marks the end of an era where we could look at Jack and feel an additional layer of playfulness. The glasses always kept naysayers from entirely buying into moments like “Dark Knight” and “DRIP DROP.” No longer. Where Loose was about the formation of Jack Harlow’s imminent rapper swagger, the removal of the glasses and the Bryson Tiller feature tell us that we’ve arrived in a new sense. Jack Harlow has unlocked a new level of camera presence and positive energy. It’s a visual syntax move that tells us a new dawn is approaching.

“THRU THE NIGHT” is a fantastic video, no two ways about it. It’s breezy, easy to follow, colorful without being overbearing, and teases us to no end. Jack looks comfortable on-screen; his motions are fluid. The scene is fresh for his canon, and the B-roll makes works to keep us engaged. “THRU THE NIGHT” has Jack Harlow knocking on the door of stardom. It’s a song engineered for radio that neither looks no sounds soulless. His smile is magnetic; his wardrobe is fitting. After three years of steady releases, Jack finally looks the part of a budding star; he raps the part, too. All in due time. 



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