Chicago Top 50 Music Video Countdown: The 2025 Archive

Every year, Chicago artists push the visual bar higher — telling our stories through lenses that reflect grit, creativity, ambition, and truth. Music videos are no longer just visuals to accompany a song; they’re statements, short films, and cultural timestamps.

The Top 50 Music Videos represent the best of that evolution.

These videos stood out not just because of budgets or popularity, but because of vision. Direction. Performance. Cinematography. Storytelling. Impact. Each entry on this list captures a moment in Chicago culture and translates it into something unforgettable on screen.

This countdown isn’t about clout — it’s about craft.

From bold concepts to raw authenticity, these Top 50 videos showcase why Chicago continues to influence music and visual culture worldwide. Whether you’re an artist, filmmaker, or fan of the culture, these selections represent excellence at the highest level.

Welcome to the Top 50.

#50 — Sunday Dinners

Artist: Jay Lyn Gatz ft. Blu

There is no better way to end a Top 50 than with “Sunday Dinners” — a record that feels like home, history, and healing all wrapped into one. The nostalgia hits you immediately, as Jay Lyn sits down on the couch with the TV Dinner and how it cuts to a group of friends, having fun while sitting on the couch. The song is packed with wordplay, smooth delivery by both Artists and it does give the effect of wanting to sit down and listen to it while having a Sunday Dinner.

#49 — Road Runnin

Artist: NewWaveE

“Road Runnin” is built for the moments between destinations. NewWaveE captures that feeling of always being in motion — whether physically, mentally, or emotionally. The beat is captivating and NewWaveE conquers it, and comes on the track with a delivery that you have to listen and tune into. The fast pacedness of traveling in the car, and always being on the move highlights always being on the move and constantly being on the grind. A relatable track with a symbolic visual to match.

#48 — Bloody Valentine

Artist: MIRIAH.

“Bloody Valentine” is a combination of R&B, Pop, and ALT in its nicest fashion. The video starts off with incredible symbolism, showing how it feels to be feeling alone while in a party, typically during a heartbreak. The lighting is moody, a bit dark, but the beat is full of life, creating a mixture of emotions when watching the visual. It’s a soft song packed with a high quality visual and it brings the song to life.

#47 — Fkin It Off

Artist: Mikee

Mikee’s “Fkin It Off” is a high energy track from “The Chi” actor that showcases his versatility from being an actor and being an Artist, and it appears he can drive in both lanes pretty well. The video is simple but fun, and it captures a day full of shopping, a bit of partying, and overall having a good time. The beat is energetic and it's a song that can fit any setting, whether you’re driving your car, in the gym or turning up at a party, this record can get played.

#46 — I Can Do That

Artists: Raymi The Artist x Heavy Crownz x Chai Tulani

“I Can Do That” is a song packed with smooth vocals, witty wordplay, and a smooth beat to match the flirtatious aesthetic. Heavy Crownz came packed with the punchlines, Raymi floated with her pen, and Chai fluidly mixed in his rapping and singing ability, the three curated a perfect summer track that feels timeless. Visually, the effects and lighting produce a soft touch and sets the mood that matches the vibe.

#45 — Middle Man

Artist: Jeff K%NZ

“Middle Man” is a highly creative visual where immediately it captures your attention within the first 5 seconds. Jeff K%NZ is in a pillar, and you can only see him from the neck up, as it appears to be a moving statue. This is the kind of record you play when you’re sorting through your own storm, trying to figure out if you’re the one making moves — or just stuck being the one making it happen for everybody else.

#44 — JAIYÉ

Artist: Koray ft. Kordy Blakka

The word jaiyé (meaning “enjoy life”) isn’t just a hook — it’s a mental soundtrack. Koray and Kordy Blakka make this joint feel like a cross‑continental celebration, bridging Afro‑influenced bounce with modern hip hop cadence. The two travel on a jet, encapsulating how high their happiness is and the levels that people should go to enjoy themselves.

#43 — I’m Sprung

Artist: Young Chop

Young Chop’s take on “I’m Sprung” flips the T-Pain classic into a slow-drip confession. It’s a remix, a rework, and a rebrand all in one as Chop is talking his own talk over the echo of an R&B moment we all will remember. With Chop being one of Chicago’s prominent producers, especially during the rise of Drill, it’s only right to showcase his versatility with a track like this one.

#42 — Outside (Gyal Dem)

Artist: Ifeanyi Elswith

“Outside (Gyal Dem)” is a breath of fresh air — sunny, stylish, and still rooted in city cool. Ifeanyi’s voice floats over a smooth Afro-influenced rhythm, with Chicago undertones — making this one perfect for rooftop day parties or late-night soft linkups. The video is light and colorful, with dancers outside corner stores, girls stepping out in sundresses and sneakers, and overall a good time is being captured. The girls picked up their pen on this one and delivered a hit.

#41 — Trap Spot

Artists: Hardknock x Matt Money

“Trap Spot” has a beat that pulls you in and Hardknock and Matt Money made sure to paint a picture with their lyrics. Another video shot by Clark Airlines, the effects bring the gritty lyrics to life as it symbolizes the chaos and all possible things that can go wrong while being at a Trap Spot. There’s many points of symbolism throughout the video and between the 808’s and lyrics, it’s a short story about the Trap Spot.

#40 — Club Popeyes

Artists: Naim Matthews x KingPinRue x MG Marz

“Club Popeyes” is a chaotic, hilarious, entertaining, shocking, and creative song that will keep your attention from beginning to end. This is one of the most fun records on the countdown, but it’s got teeth. The concept alone makes it an instant classic: turning a fast food spot into a night club, complete with drums - chicken drums as well - that slap and symbolic lyrics that are catchy. The three Artists took full advantage of the Don Julio collab and came up with an anthem that is unforgettable.

#39 — Tina Snow

Artist: Ashlee Bankz

Ashlee Bankz’s “Tina Snow” is a direct shoutout to her alter ego — and a nod to the icy energy. As powerful as the beat is, Ashlee hops on it with full control and commands attention with her delivery as well as her penmanship. Visually, shot by Clark Airlines, the video takes advantage of its white background and pours out constant effects with creativity highlighting the originality of the single.

#38 — Emergency

Artist: Tink

Tink’s “Emergency” is what happens when real feelings meet boss-level delivery. It’s soft in sound but serious in tone — a warning shot wrapped in velvet. This song is packed with her powerful voice and as she sings to her lover, she does it with that signature Chicago edge that makes her music undeniable and unshakable. From the opening scene, the video is drenched in moody red lighting in an ambulance, visually adding to the word play of it being an Emergency. As always, Tink’s creativity shines bright in her pen as well as her visual.

#37 — GOOD MORNING AMERICA

Artist: Ausar

Ausar’s “GOOD MORNING AMERICA” doesn’t feel like a song — it feels like a broadcast of how a lot of us are feeling on a daily basis right now. Visually, it captures Ausar rapping in a suit in a mirror and lyrically, the song encapsulates emotionally how a lot of people feel with the current state of the world. It’s one of those songs that can probably make your morning a bit better with a relatable track.

#36 — Go!

Artist: Enama

Enama’s “Go!” is exactly what it sounds like — a command, not a suggestion. The record explodes from the first second like someone just kicked the door off the hinges. It’s raw, chaotic, and fast, but every move is intentional. A twerk/footwork track laced with bounce, energy, and pure foot-on-the-gas momentum, this song needed a visual to match and with the color schemes, roller skating scenes and high energy, the visual delivered just that.

#35 — Oh Brother

Artist: Munna Ikee

Munna Ikee’s “Oh Brother” hits different from the first bar. This ain’t just a song — it’s a message, a memory, and a moment of mourning, all laced into a slow-burning drill beat. Visually, it contains a lot of symbolism throughout the video, especially when Munna is standing over a hole with a shovel. But the overall sound of this track, it’s packed with emotion and vulnerability, to a point where no matter what you’ve been through, it will trigger self-reflection or grievances from your past.

#34 — UGK

Artist: Panamera P ft. Ju Jilla & Richie Wes

Panamera P’s “UGK” has a beat that automatically lets you know that real bars and strong delivery is on the way, and it’s evident that that recipe was being cooked when you have Ju Jilla and Richie Wes as the features. The visual is simple but captivating as it focuses heavily on the lyrics and the execution of the song. Each Artist laid out their verse and did what they do best, deliver real rap.

#33 — Party in the Burbs

Artists: DollaGreedy Chalo ft. O Skudda

“Party in the Burbs” is what happens when the block pulls up in a gated community and throws a function that flips the whole zip code upside down. From the second the record starts, you’re already hooked as you hear an insane sample from “Party in the US” by Miley Cyrus and Chalo and O SKudda definitely lived up to the hype of this classic. The visual matches the intensity as it’s a Project X type of party vibe but without the danger.

#32 — In Front of the Building

Artist: Ju Jilla

There’s songs you just listen to, and then there’s joints like “In Front of the Building” — records that place you in the moment. This isn’t a track built for the club, or a playlist favorite. It’s a scene, a feeling, a corner of the city frozen in time. And Ju Jilla doesn't just rap it — he lives it. The video for “In Front of the Building” is exactly what the title promises: it’s Ju Jilla posted, front and center, right where the story begins as he’s a true storyteller.

#31 — Stick Up

Artist: Raq Baby

Sampling the “Year 3005” by Childish Gambino, this record commands your attention and Raq Baby did not disappoint on the nostalgic record. On a melodic and high spirited beat, Raq Baby delivers vocals to match while the visual is the complete opposite. As nice as the song sounds, Raq Baby is pulling off a heist and has a security guard tied up during the robbery.

#30 — 95 South

Artists: The Cool Kids, A-Trak, Sango

When “95 South” dropped, it wasn’t just another link in The Cool Kids’ catalog — it felt like a homecoming, but in motion. This record isn’t trying to recreate the past — it’s building from it. It’s smooth, confident, and stamped with the kind of weight that only comes from longevity. Visually, it has a retro type of aesthetic with the quick cuts and flashing colors, and the throwback jerseys and attire.

#29 — My World

Artist: Chuckyy

The video for “My World” doesn’t feel like a rap video — it feels like a documentary chapter broadcasting how to have fun. The visual is filled with city textures, a carnival, rollercoasters, and high energy of a group having fun and the song matches the vibe. The decision to run around in suits as they’re having a blast was a nice creative touch as well as the overall execution of this song.

#28 — WISCANSIN

Artists: Jay Wood ft. Henry Verus

“WISCANSIN” is the kind of record that pulls up slow but sits heavy. The beat is smooth and captivating and both artists came on exactly how one should and the video definitely matches the vibe. It has serene shots of nature, and a shot with dancers spinning on poles in a barn that appeared to be angelic. The entire demeanor of this video is calming like Jay Wood’s delivery.

#27 — 2 C’s

Artists: Murf Dilly & Jeremih

There’s something magnetic about the “2 C’s” video — the way it’s shot, lit, and paced makes it feel like you just pulled up to a quiet flex in motion. Scenes cut smoothly between Murf Dilly delivering bar-for-bar energy and Jeremih gliding through the hook like silk. There’s women in ski masks dancing in colorful lighting, and while dancing, some are playing the violin, which is not something you typically see in a music video.

#26 — CUTWATER

Artist: Glizzy Glow

“CUTWATER” is a fun, high energy track with an entertaining visual to match. The quick effects and color palettes throughout the video encapsulates the hype around the drink that made headlines over the summer. Glizzy Glow’s presence commands the screen as well as the juke/footwork beat that can influence anyone to get up and dance. This is easily a single that can be played in the gym or in the club.

#25 — Chvmpion

Artist: Seedz ft. Joel Q & Heavy Crownz

Chvmpion is a track packed with lyrical skill and flawless delivery from Joel Q and Heavy Crownz. Shot by Clark Airlines, the video feels like a documentary turned cinematic. The artists rap from symbolic areas that match their upbringing. Every effect in this video showed up just like every punchline did in this song. The quick flashes of Chadwick Boseman and Nipsey Hussle in the beginning sets the tone of Champion energy.

#24 — JUKE BACK (Astronautflee Remix)

Artist: Del Marie

JUKE BACK is a highly creative track with an extremely creative video to match. The song has a modern take on juke and footwork culture that flips the sound into something psychedelic and futuristic. The video leans into that energy fully. Directed and produced by Del Marie with co-production by Jaasyn, the visual is dreamy and distorted, with a futuristic inclusion of spaceships and aliens.

#23 — How To Bip

Artists: Rockout Danny, G Herbo, VonOff1700

How To Bip has an incredible beat that Rockout Danny, Vonof1700 and the seasoned vet G Herbo all hopped on and gave justice. Visually, the video (directed by Sergio Esparza) is dynamic and bold. The camera moves with urgency, often handheld, bringing viewers into tight corners and street corners, and the quick flashes of all the nice vehicles brought this song to life.

#22 — NEXT TO YOU

Artists: Panamera P ft. Philmore Green, Kid Breeze, Rufus Sims, Ju Jilla

Next To You is smooth street soul at its finest — a grown man’s anthem for loyalty, love, and standing tall through hard times. Panamera P leads a stacked lineup of Chicago spitters, each bringing their own individuality to compliment the beat. The video, shot by QNCY, captures the essence of the track with grace which allows Philmore Green, Kid Breeze, Rufus Sims, and Ju Jilla each take turns passing the mic.

#21 — Move Pt. 2

Artists: Mello Buckzz & Monaleo

Move Pt. 2 kicks down the door with full-force energy and doesn’t let up for a second. Mello Buckzz teams up with Monaleo to deliver a heavy-hitting anthem made for dancing, twerking, footworking and making people move — literally. Together, they create the kind of chemistry that feels natural, not forced. The video, directed by Sergio Esparza and presented by No More Heroes, is a masterclass in movement with a creative touch.

#20 — Still Boppin

Artist: Lil Kemo

When it comes to dance culture in Chicago, Lil Kemo’s name rings bells — and Still Boppin is another full celebration of that legacy. The track is infectious, built for footwork and movement, and his cadence rides the beat like a pro. The video, shot by QNCY, is a nonstop motion reel. Dancers from across the city come out in force — on sidewalks, in alleys, in living rooms.

#19 — Counterfiet

Artists: Shawnna & Lstreetz

Shawnna and Lstreetz came through swinging on Counterfiet — a razor-sharp anthem calling out everything fake in the game. The beat is cold, almost sinister, but both emcees float like it’s nothing. Directed by Clark Airlines and Churchboy Scotty, the video matches the energy. Flashy visuals meet hard looks. It’s black leather, high-speed cuts, and fierce energy from start to finish and the quick cameo with Twista is entertaining.

#18 — Woes of the World

Artists: Saba & No ID

When Saba links up with No ID, you expect greatness — and Woes of the World delivered. This track feels like a journal entry turned into scripture. Saba lays out anxiety, pressure, and hope all in one breath. The video, directed and edited by Andrpw, is artful and abstract. Blurry silhouettes, glitch effects, slow pans across city landscapes — it all feels like memories playing in reverse.

#17 — Coco Gauff

Artists: Mick Jenkins & EMIL

Coco Gauff isn’t just a clever title — it’s a full-on metaphor for focus, discipline, and unapologetic Black excellence. Mick Jenkins teams up with EMIL for one of the most elevated, poetic records on the list, paying tribute not just to the tennis prodigy Coco Gauff, but to what she represents: grace under pressure, calculated aggression, and winning on your own terms.

#16 — Power Ranger

Artist: Star Bandz

Star Bandz came through like a force on Power Ranger — loud, colorful, and unapologetically raw. From the jump, the beat kicks in with bounce and authority, and she matches it bar for bar with confident, clever rhymes. The video, directed Christian Loggins, takes her energy and amplifies it with bold color grading, creative transitions, and a whole lot of personality.

#15 — Mista West$ide

Artist: Mike DFG

Mista West$ide is a full-out, action packed, entertaining, attention grabbing, “John Wick” flex. Mike DFG dropped this track like a brick through a window — hard-hitting, unapologetic, and full of attitude. The song is a personal anthem where he reps where he’s from with pride, but also shows you why his name holds weight. This visual is rich with stunts and choreography - all performed by Mike DFG himself.

#14 — Quality Over Quantity

Artist: Polo G

Quality Over Quantity is Polo G back in his reflective bag. The beat is slow, heavy, and melodic — the kind of instrumental he’s known for skating on. The video, directed by Polo himself along with Diamond Visuals, leans into a grayscale palette with flashes of gold — representing growth through struggle. It’s a visually metaphoric video to match the track’s tone.

#13 — Get Loose

Artists: Taylor Bennett x Tha Pope

Taylor Bennett and Tha Pope dropped a feel-good anthem with Get Loose — and the title says it all. It’s a celebration of freedom, movement, and letting go of the weight. It was only right that Taylor included the legendary Pope to collaborate on this track and visual. The video (shot by Milky) is vibrant and stylish, featuring daylight colors, rooftop energy, and organic city vibes.

#12 — Reason

Artist: G Herbo

Reason is one of the most introspective records G Herbo dropped in 2025. It's not just about what he's been through — it's about why he's still here. Over a moody, minor-key beat, he raps like someone who’s walked through every kind of fire and came out clearer. The video, directed by LVTR KEVIN, walks the same emotional line with black-and-white imagery and elegant shots.

#11 — No Adlibs

Artist: King Louie

No Adlibs is proof that King Louie doesn’t need much to say a lot. The song strips it all the way back — no hooks, no gimmicks, no sing-along moment. Just Louie, a cold beat, and a presence that commands attention. He raps with that signature blend of menace and confidence. The video captures all of Chicago’s beauty as well as a day in the life of the legend.

#10 — In This Club

Artists: DCG Shun x DCG Bsavv feat. YFG Fatso

If there was one song on this list that captured the exact feeling of walking into a party that’s already turnt — it’s In This Club. The DCG Brothers and YFG Fatso teamed up on this track and walked on the beat. The song is delivered with high quality visuals, encapsulating each Artist’s skill and influence.

#9 — Went West

Artist: BabyChiefDoit

Went West will instantly grab your attention with its powerful beat that feels like you’re in a stadium when it comes on. Filled with high energy, BabyChiefDoit comes on the track with strong vocals and the video matches the vibe. The video highlights Chief’s rise as he celebrates his success with fans while on stage performing during Lyrical Lemonade’s Summer Smash.

#8 — Top Of Cars

Artist: Lil M.U.

Lil M.U. sparked a whole movement with Top Of Cars. What started as a catchy bop turned into a full-on dance sensation across Chicago and beyond. From school gyms to block parties to club nights, this track lit the city up — and the video doubled down on the vibe. Lil MU is rapping from the roof of a car like it’s her personal stage, and it is clearly a great time.

#7 — FLAVAZ

Artist: Recoechi

Recoechi came through swinging on FLAVAZ — a bar-heavy, high-concept video with clean fits, bold lighting, and camera angles that move like they’re part of the rhythm. Even though the video has style, it still doesn't outshine the wordplay and how the song is packed with slick transitions and cultural references.

#6 — WHATEVER U WANT

Artists: G Herbo ft. Jeremih

This is G Herbo at his smoothest — and most reflective. WHATEVER U WANT brings street stories into luxury settings, bridging Herbo’s grit with Jeremih’s effortless R&B flair. The video is plush: candle-lit scenes, crisp fashion, and intimate vibes. It’s a break from the usual drill aesthetic and shows Herbo in full control of his evolution.

#5 — the word

Artists: Vic Mensa ft. Mick Jenkins

A politically-charged, lyrically dense drop with a moody visual concept by Moja Robinson and Brandon Hoeg. Vic and Mick step into a shadowy, poetic space with this video and a song with powerful delivery. Mick’s pen cuts through with clarity, flipping layered metaphors, biblical nods, and cultural critique.

#4 — Do U

Artists: Do Or Die ft. Twista & Johnny P

A long overdue, but still highly anticipated, smooth return from the Chicago Legends, updating their classic single “Do U” with lush visuals and elevated production. It's polished and soulful, shot with love for the era that birthed it, while showing the legends aging gracefully in the booth and on screen.

#3 — Tree

Artists: Chance The Rapper ft. Lil Wayne & Smino

A soulful, poetic cut featuring Lil Wayne and Smino with Chance stepping in as director. The surrealist visuals bring the metaphor of growth and roots to life. This video has many layers of creativity which makes this a video that has a high rewatch value. Chance as the Director, the Legendary Lil Wayne on the track, and a fire verse from Smino is the perfect recipe.

#2 — Went Legit

Artist: G Herbo

With raw intensity and confident storytelling, this track finds Herbo reflecting on growth. The video captures him in elevated spaces while still grounded in familiar environments. Not only is this a record loved in Chicago, but its reach has made it a national anthem for hip hop in 2025. Many different artists have tried to rap over this beat, but it belongs to G Herbo.

#1 — Ride Remix

Artists: Chance The Rapper ft. Do or Die & Twista

Three generations of Chicago legends linked up for this one, and the result was nothing short of iconic. Ride Remix brings Chance, Twista, and Do or Die into the same room — both literally and creatively — with a visual that plays like a love letter to the city. This video is a true celebration of the city’s history and future.