[Hip-Hop Classics] Timeless HIPHOP / Golden Oldies
Hip-hop hadn’t been very popular in Japan for a long time, but it’s recently started getting attention, thanks in part to the spread of MC battles.
That said, even if people know recent tracks, many might not be familiar with the older ones.
So this time, we’ve picked out some classic hip-hop tracks recommended for those listeners.
We’ve mainly chosen songs from the 1980s to the 2000s, so you can also get a sense of hip-hop’s history.
Please take your time and enjoy.
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- [Japanese Hip-Hop] Classic Tracks of Japanese Rap
- A Guide to Western Rap: Introducing Legendary Classics
- [2026] A Compilation of Classic and Popular Tracks for Hip-Hop Beginners
- Stylish hip-hop! A roundup of classic albums in Western jazzy hip-hop
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- Japanese Hip-Hop Popularity Rankings [2026]
- From Pop to Hip-Hop: Nostalgic Rap Recommendations for People in Their 30s
- Western Hip-Hop Popularity Rankings [2026]
- [Western music] Classic upbeat hip-hop tracks
[Hip-Hop Classics] Standard HIPHOP / Timeless Masterpieces (131–140)
Me And My Crazy WorldLost Boyz

Lost Boyz, a hip-hop group from New York, USA.
Their 1997 release “Me and My Crazy World” is a supreme number whose groovy rap instantly cranks up the excitement for summer.
At the same time, the track has an interesting twist, featuring strings and synth tones that sparkle like glass beads.
The quirky, story-driven music video—so characteristic of the ’90s—is also worth checking out, so why not watch it together with the song?
Can’t Tell Me NothingKanye West

Kanye West is one of the defining figures of the hip-hop scene since the 2000s, achieving extraordinary success both as a rapper and as a producer.
The song “Can’t Tell Me Nothing,” included on his third album, Graduation, released in 2007 to massive success, features lyrics that clearly convey what was going through Kanye’s mind at the time—a figure whose bold actions and statements often sparked controversy and attracted intense scrutiny.
They can be read as characteristically confident, yet they also carry a certain melancholy.
You can even glimpse an intellectual side in his quoting of a Bible verse.
All in all, it’s fair to call it a masterpiece that encapsulates Kanye’s multifaceted appeal.
Losin ControlRuss

A song by American hip-hop artist Russ about his first girlfriend, whom he dated when he was 17–18 years old.
It was released as a single in 2016, and the music video was directed by Essgar Estevez.
Best I Ever HadDrake

This track was released as a single in 2009 by Drake, the charismatic Toronto-based rapper who has also gained attention as an actor.
It samples Hamilton, Joe Frank & Reynolds’ 1975 track “Fallin’ in Love.” The music video was, remarkably, overseen by none other than Kanye West.
Among Drake’s many songs, this one remains a fan favorite and continues to enjoy strong popularity.
Hustlin’Rick Ross

His stage name was taken from a real, famous dealer, and his debut track addresses that.
The rapper Rick Ross drew attention when most of the albums he announced for release debuted at No.
1 on the charts.
As is often the case with unruly rappers, he was arrested in 2015 on kidnapping and assault charges.
It’s something we can now look back on as a thing of the past, but because his skill and taste were so strong, his fans were very worried about him at the time.
In conclusion
Hip-hop began gaining popularity in the 1980s and now reigns as one of the scene’s top genres.
Although its history is relatively short compared to other genres, it has changed dramatically—today’s hip-hop looks very different in style from what it was 20 to 30 years ago.
Let this article be your gateway to diving deep into the world of hip-hop!


