Image credit: YouTube

To celebrate YouTube’s 20th anniversary, their music head”obesessively sorted through thousands of options” to find the top 20 Hip Hop videos.

What are the greatest hip hop music videos ever made? The question could spark endless debate, so to put the question to rest is a definitive list made in celebration of YouTube‘s 20th Anniversary and Black Music Month (tell us in the comments why it is not the definitive best list!)

YouTube’s Head of Music Culture, Tuma Basa, has highlighted the most iconic hip hop music videos of all time. Drawing on decades of experience and, according to YouTube, “armed with unprecedented access, staring down a monstrous scroll of data”, Basa nailed down the 20 defining videos in hip hop.

YouTube wrote: “It wasn’t just about view counts; it was about the pulse of the culture. He weighed the raw power of the visuals, the seismic impact each video had on the streets, in the clubs, on the global stage. And then, he infused it with his own deeply personal taste, a gut feeling honed over years of shaping the sound of a generation.”

The reach of the video still mattered, with Basa telling Complex: “If view count wasn’t part of the filter, Busta Rhymes, with his legendary video catalog, would have easily had five spots on the list.” Basa said that the finalists were picked on a combination of “impact of the song, memorability of the visuals, and snapshot of the time”.

The Definitive Top 20 List

After weeks of obsessive sorting and deep cultural consideration, Basa’s list has emerged. From modern masterpieces to 90s classics, this is a journey through hip hop’s visual evolution.

20. OutKast – Hey Ya!

19. Snoop Dogg – Sensual Seduction

18. Future – Life Is Good (feat. Drake)

17. 50 Cent – Many Men

16. Warren G – Regulate (feat. Nate Dogg)

15. Nicki Minaj – Beez In The Trap (feat. 2 Chainz)

14. Lil Baby – The Bigger Picture

13. Eminem – Stan

12. Lil Wayne – Lollipop

11. Fugees – Killing Me Softly With His Song

10. The Throne – Otis

9. Soulja Boy – Crank That (Soulja Boy)

8. Lauryn Hill – Doo Wop

7. Drake – God’s Plan

6. Lil Uzi Vert – XO Tour Llif3

5. Kendrick Lamar – Humble

4. Missy Elliott – Work It

3. 2Pac – California Love (feat. Dr. Dre)

2. Travis Scott – Sicko Mode (feat. Drake)

1. Ice Cube – It Was A Good Day

Handkerchiefs, Kleenex, and Beautiful Chaos

Basa’s analysis offers a fascinating perspective on how music videos have changed. He identifies two distinct eras: the “Handkerchief Era” and the “Kleenex Era.”

The Handkerchief Era of the 90s and 2000s was defined by big-budget, cinematic videos “shot on film, built to last, just super evergreen.” These were mini-movies designed to stick around. In contrast, the Kleenex Era emerged with affordable DSLR cameras, leading to more “disposable” videos with quicker turnarounds and shorter cultural shelf lives.

So how did a more recent “Kleenex Era” video like Travis Scott’s “SICKO MODE” land at #2? Basa calls it “beautiful chaos.” He explains, “It’s like three videos in one. The hyper-edits are bananas… If you watch a lot of music videos, that density matters.” Directed by the legendary Dave Meyers (who also directed #4, “Work It”), the video is a visually packed tribute to Houston that rewards repeat viewings.

And for the #1 spot? Ice Cube’s “It Was A Good Day” is a masterclass in storytelling. “This song was a mini-motion picture, and it’s kind of a precursor to the classic movie Friday,” Basa notes. “It’s a perfect snapshot of the 90s.” The video’s narrative, iconic scenes, and cliffhanger ending (which leads into the “Check Yo Self” video) cement its status as a timeless piece of art. “Our grandkids are gonna be rocking it. That’s durability!”

The list is sure to ignite conversation, but more importantly, it serves as a powerful tribute to the artists and directors who shaped the visual language of hip hop. Feel free to tell us your thoughts in the comments below and discuss what the list should look like from your perspective.