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This Day in Hip-Hop and R&B History: February 21

Feb. 21 has hosted events that have influenced the evolution of Hip-Hop and R&B, from groundbreaking singles and album releases to unforgettable performances and cultural moments. One industry figure born…

Rapper Tyga arrives at the 54th Annual GRAMMY Awards held at Staples Center
Photo by Jason Merritt/Getty Images

Feb. 21 has hosted events that have influenced the evolution of Hip-Hop and R&B, from groundbreaking singles and album releases to unforgettable performances and cultural moments. One industry figure born on this day is Savannah rapper Duwap Kaine, born in 2002. The up-and-coming star is known for his various projects, including Underdog, Bad Kid from the 4, Faith Like Esther, and After the Storm. Other artists whose birthdays fall on this date include rapper and singer-songwriter Charlieonafriday (2003) and Indiana rapper Kid Quill (1994). 

Breakthrough Hits and Milestones

Many culture-defining hit singles and albums have been released on this date over the years:

  • 1995: DJ Quick's third album, Safe + Sound, was released. It would go on to peak at No. 14 on the Billboard 200 and No. 1 on the Top R&B/Hip-Hop Albums chart.
  • 2006: Los Angeles hip hop trio Dilated Peoples released their fourth album, 20/20. Featuring production by The Alchemist, DJ Babu, and Evidence, it debuted at No. 97 on the Billboard 200 and No. 35 on the Top R&B/Hip-Hop Albums chart. The project also peaked at No. 10 on the UK R&B Albums chart. 
  • 2006: Shaggy 2 Dope dropped his debut album, F.T.F.O (Fuck The Fuck Off), through Psychopathic Records. With a single feature from Twiztid, the album debuted at No. 88 on the Billboard 200 and No. 7 on the US Billboard Independent Albums chart. 
  • 2012: Chiddy Bang released their debut album, Breakfast. Supported by the singles “Ray Charles” and “Mind Your Manners,” the project reached No. 2 on the Top R&B/Hip-Hop Albums chart and No. 8 on the Billboard 200. 
  • 2012: Tyga released his second album, Careless World: Rise of the Last King. It spawned the hit singles “Rack City” and “Faded,” which peaked at No. 7 and No. 33 on the Billboard Hot 100, respectively. The album itself peaked at No. 4 on the Billboard 200 and at No. 1 on the Top R&B/Hip-Hop Albums and Top Rap Albums charts. It has since been certified platinum by the Recording Industry Association of America (RIAA) for selling over a million copies. 
  • 2020: Rapper Royce da 5'9” released his eighth studio album, The Allegory, through Entertainment One Music. The album peaked at No. 32 on the Billboard Top R&B/Hip-Hop Albums and No. 58 on the Billboard 200. 
  • 2020: YoungBoy Never Broke Again dropped his thirteenth mixtape, Still Flexin, Still Steppin, via Atlantic Records and his own Never Broke Again label. Featuring a sole collaboration with Quando Rondo on “Suited Panamera,” the album debuted at No. 2 on the Billboard 200 and topped the Top R&B/Hip-Hop Albums chart. 
  • 2022: Duwap Kaine released his single “GRG (Get Right Gang).”

Cultural Milestones

This day marks the anniversaries of various events that have impacted the landscape of Hip-Hop and R&B:

  • 1983: Michael Jackson's iconic hit “Beat It” was released as the third single from his culture-defining album, Thriller. The song topped the Billboard Hot 100 for three weeks, also reaching No. 1 on the Billboard Hot Black Singles chart (now the Hot R&B/Hip-Hop Albums chart). In 2021, Rolling Stone ranked it No. 185 on its “The 500 Greatest Songs of All Time” list. 
  • 1990: German R&B duo Milli Vanilli won a GRAMMY Award for Best New Artist at the 32nd Annual GRAMMY Awards. However, the Recording Academy revoked the award after the band members admitted they didn't sing on their album. 
  • 2018: Hip-hop phenom Nipsey Hussle discussed the development of his first and only album, Victory Lap, on The Breakfast Club. The rapper sat down with the show's hosts Charlemagne tha God, DJ Envy, and Angela Yee while wearing his clothing brand.

Notable Recordings and Performances

Feb. 21 has witnessed some groundbreaking performances and recordings that have shaped the evolution of the Hip-Hop and R&B industry:

  • 1968: R&B and soul singer Otis Redding debuted on the U.K. Singles Chart with the posthumously released single “(Sittin' On) The Dock of the Bay.” The song peaked at No. 3 on the chart and is certified three times platinum in the U.K.  
  • 1970: The Jackson 5 made their debut appearance on American Bandstand, hosted by Dick Clark. The group performed their breakout hit “I Want You Back” and their newly-released single “ABC.” Their set also included covers of “Zip-A-Dee-Doo-Dah” as well as James Brown's “There Was a Time,” showcasing their versatility as performers.
  • 1990: DJ Jazzy Jeff & the Fresh Prince became the first Hip-Hop act to perform at the GRAMMY Awards. The duo made history a year earlier when their single “Parents Just Don't Understand” won a GRAMMY for Best Rap Performance, the first hip-hop recording to achieve that feat.

Industry Changes and Challenges

The industry has suffered significant losses on this date over the years.

  • 2025: American R&B/soul icon Gwen McCrae died at the age of 81 after a long illness. She is best remembered for her 1975 smash hit “Rockin' Chair,” which peaked at No. 9 on the Billboard Hot 100 and topped the Billboard Hot R&B chart. 
  • 2025: Hong Kong singer-songwriter Khalil Fong, known for incorporating R&B and soul sensibilities in Chinese pop music, died of an unspecified illness at the age of 41. His 2016 album, Journey to the West, won him the award for Best Male Mandarin Singer at the 28th Golden Melody Awards.

On Feb. 21 we saw two albums released along with a single from Duwap Kaine. DJ Jazzy Jeff & the Fresh Prince also performed at the GRAMMY Awards, making history by becoming the first hip-hop act to perform at the awards.