On October 23, Lil Nas X's "Old Town Road" received an RIAA Diamond certification, 2019's first Diamond certification and the fastest song in history to reach this milestone.
On October 15, Tyga signed a multi-million dollar deal to be with Columbia Records.
On October 6, 2 Chainz partnered with Atlantic Records with his independent label The Real University.
On October 2, Gucci Mane partnered with Gucci.
On September 5, Nicki Minaj announces her retirement from making music to "have my family".
On July 1, Lil Nas X's "Old Town Road" becomes the longest-running hip-hop song at number one on the Billboard Hot 100 after thirteen weeks, surpassing " Lose Yourself" by Eminem, " Boom Boom Pow" by the Black Eyed Peas, and " See You Again" by Wiz Khalifa featuring Charlie Puth, which had each achieved twelve weeks at number one.
On June 20, the 2019 XXL Freshman Class was revealed, in which it included Gunna, DaBaby, Roddy Ricch, Cordae, Megan Thee Stallion, Lil Mosey, Blueface, Comethazine, Tierra Whack, YK Osiris, and Rico Nasty.
On June 9, Bushwick Bill of the Geto Boys died at the age of 52, from pancreatic cancer.
On April 21, Kanye West lead an Easter Sunday Service performance at Coachella, the group's first public performance.
On April 18, Cypress Hill receives a star in the walk of fame, making them the first Latino group to receive a star in the walk of fame.
On March 31, Nipsey Hussle was fatally shot outside his clothing store in Los Angeles, CA.
On March 26, Billboard controversially removes Lil Nas X's breakout single " Old Town Road" from the Hot Country Songs chart for "not enough elements of today's country music".
On February 28, BlocBoy JB was arrested for drug and weapons charges.
The same day that 21 Savage was released from ICE custody on bond.
On February 13, YNW Melly turned himself in to authorities and was charged with the double murder of rappers and childhood friends YNW Sakchaser and YNW Juvy.
On February 12, Mystikal was released from prison on $3 million bond.
On February 10, Cardi B won a Grammy Award for Best Rap Album with Invasion of Privacy and Drake won a Grammy Award for Best Rap Song with God's Plan.
On February 9, English rapper Cadet was killed in a car accident.
Immigration and Customs Enforcement (ICE) for having an expired visa and was revealed to be a United Kingdom national.
On February 3, 21 Savage was arrested by the U.S.
On January 27, Florida rapper Jayo Sama was killed in a drive-by shooting in West Palm Beach, Florida.
On January 25, DMX was again released from prison.
On January 23, 6ix9ine admitted to being guilty of all charges related to racketeering and gang violence.
On January 8, Cupcakke was hospitalized following a suicide scare.
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