10 Sad Hip Hop Songs Of The 90’s

The 10 sad hip hop songs of the 90's are filled with stories of broken hearts, lost loves, death, depression and reminiscing of all good that once came before the dark times. Aside from happiness and partying, music is also extremely useful when it is used to zero in on a struggle which one protagonist (the performer) is facing in his life. That struggle can range from the death of a close friend to a relationship that has sustained damage. Grab a tissue box or two and press play.

  1. "Tha Crossroads" by Bone Thugs-N-Harmony. Known as their most popular and highest charting single to date, Bone Thugs-N-Harmony's "Tha Crossroads" is a mass dedication to a number of close friends and colleagues of the group who had passed away, most prominently Eazy-E.
  2. "I'll Be Missing You" by Puff Daddy featuring 112 and Faith Evans. One of Puff Daddy's (or Diddy's, we should say) highest charting singles ever, "I'll Be Missing You," was created from a sample of The Police song "Every Breath You Take" in order to make a tribute to his slain friend, the legendary rapper The Notorious B.I.G.
  3. "Miss You" by Aaliyah. Released after her unfortunate demise, Aaliyah's "Miss You" was penned by herself beforehand and revolved around a relationship facing the obstacle of one lover going away to college. However, the song was then aimed as a tribute to Aaliyah, thus the lyrics and the tone now present with a double meaning of sorts to them.
  4. "Before You Walk Out of My Life" by Monica. One of Monica's very first singles from her debut album, "Miss Thang," the Hip Hop/R&B song "Before You Walk Out of My Life" tells of a broken relationship and a woman who begins to reminisce about what has happened and what she will miss about her lover.
  5. "Keep Ya Head Up" by 2Pac. With a beat sample borrowed from "Be Alright" by Zapp and Roger as well as a chorus sampled from "O-o-h Child" by the FIve Stairsteps, 2Pac's "Keep Ya Head Up" is an epic sad hip hop song from the 90's that depicts a series of tragic events which one woman undergoes.
  6. "Changes" by 2Pac. Featuring a sample from "The Way It Is" by Bruce Hornsby and the Range, Tupac Shakur's "Changes" is a sad Hip Hop song (released after his demise) that reflects on various society issues ranging from police brutality, gang violence and drugs to racism.
  7. "All Cried Out" by Allure featuring 112. Originally performed by Lisa Lisa and Cult Jam with Full Force in the mid-1980's, Allure and 112's version of "All Cried Out" had managed to outperform its original counterpart on the pop charts. This sad Hip Hop song revolves around a broken relationship and how both sides are dealing with it.
  8. "Ex-Factor" by Lauryn Hill. This sad Hip Hop song borrowed a sample from "Can It All Be So Simple" by the Rap group, the Wu-Tang Clan. The song is a slow Rap/R&B love ballad that chronicles a tale of lost love and an ex-lover with whom the female protagonist is struggling with emotionally.
  9. "I Ain't Mad At Cha" by 2Pac. Tupac Shakur pieced this song together as a tribute for the people who he had known before he became a rap superstar, how he lost touch with them, and those who abandoned him after his success. The fact that this was released immediately after his death amplifies its themes.
  10. "Always Be My Baby" by Mariah Carey. This mid-1990's sad Hip Hop song was nominated for a Grammy in its year of release and broke charts all across the board. "Always Be My Baby" depicts a concluded relationship and a female protagonist that is optimistic that her lover will return to her once he figures out that he misses her.
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