Nostalgic Playlist: Favorite Hip-Hop Hits from the ‘90s

The 1990s was perhaps the golden age of hip hop. It was the decade that bred innovative rappers who crafted meaningful lyrics and ingeniously invented complex wordplay. Not only did they exemplify the genre’s fresh, energetic sound, but they each owned an individual sound that paved way for rap music to assume a dominant position in pop culture. So, hearing some of the greatest hip-hop voices of the ‘90s today will definitely get you in a nostalgic mood.

SoJones compiled a list of unforgettable rap songs that evoke childhood memories in various ways. Here’s a collection of hits from the ‘90s era that will take you back to the good ol’ days. Enjoy!

“California Love”

By: 2Pac feat. Dr. Dre and Roger Troutman

“California Love” was deemed as one of 2Pac’s most popular and successful songs. It was dropped as 2Pac’s comeback single upon his release from prison in 1995. 

 “U Can’t Touch This”

By: MC Hammer

A multi-platinum hit, “U Can’t Touch This” became MC Hammer’s signature song. It won Grammy Award for categories Best R&B Song and Best Solo Performance in 1991.


By: Jazzy Jeff and Fresh Prince (Will Smith)

With its warm, laid-back party tune, “Summertime” was a huge success commercially and chart-wise. It secured a Grammy Award for Best Rap Performance by a Duo or Group in 1992.

“Dear Mama”

By: 2Pac

One of 2Pac’s most respected songs, “Dear Mama” earned accolades for its emotional and introspective lyrics. In fact, it was included 0n the list of the 1001 Songs You Must Hear Before You Die: And 10,001 You Must Download.

“Tha Crossroads”

By: Bone Thugs-n-Harmony

“Tha Crossroad” was a smash hit worldwide, boasting fast rhymes, soft delivery, and heartfelt lyrics. The song was dedicated to Eazy-E, the group’s mentor who died of AIDS.

“Gangsta’s Paradise”

By: Coolio feat. L.V.

One of the best-selling singles of all time, “Gangsta’s Paradise” was a Grammy Award-winning rap song that was a reworking of Stevie Wonder’s 1976 song “Pastime Paradise.”


By: Salt-N-Pepa

A chart-topper, “Shoop” was one of the group’s most successful singles. The success of the song, as well as of the follow-up single, “Whatta Man,” helped the album Very Necessary sell five million copies in the United States alone.



Arguably the group’s signature song, “Waterfalls” was a Grammy Award-nominated track that tackled the issues of drugs dealing and HIV.

“Set Adrift on Memory Bliss”

By: P.M. Dawn

“Set Adrift on Memory Bliss” elicited peaceful, psychedelic vibes that stood out from the aggressive gangsta rap that was popular back then. It was covered by the Backstreet Boys on their second album in 1997.

“Jump Around”

By: House of Pain

“Jump Around” was a classic smash hit that boasted horn-heavy opening transition, getting you all pumped up. The song still gets played at sports events today.

“Feel Me Flow”

By: Naughty by Nature

Named “coolest rap song of the 1990s” by Rolling Stone, “Feel Me Flow” peaked at #17 on the Billboard Hot 100 and at #3 on Hot Rap Singles.

“Mr. Wendal”

By: Arrested Development

Contrary to first impression, the song was not based on a real person. It seemed like a tribute to a man named Mr. Wendal, but “Mr. Wendal” was a socially conscious song that dealt with homeless people.


By: Warren G.

A Grammy Award- nominated single, “Regulate” was noted for its long bass hits, phenomenal beats, and cool synths.

“Killing Me Softly”

By: Fugees

Fugees’ smooth and soulful rendition of Roberta Flack’s “Killing Me Softly” made an indelible mark on the hip-hop game. With Lauryn Hill singing the lead vocals, the message of the song was captured with more upbeat, hip-hop flare.

Let us know if you’re still listening to these songs in the 21st century!

Image Courtesy of InSapphoWeTrust via Flickr

Bea Canuel

Bea Canuel

Bea Canuel holds a Bachelor's degree in Mass Communication and finds her stride in content writing and editing. Aside from being a certified logophile, Bea is also a bookworm and filmaholic in the making, who goes crazy over fashion, sweets, and anything vintage.