This article summarizes the events, album releases, and album release dates in hip hop music for the year 1999.
| Artist | Project | Peak position | |
|---|---|---|---|
| "What's It Gonna Be?!" | Busta Rhymes featuring Janet Jackson | 3 | |
| "Jamboree" | Naughty By Nature featuring Zhané | 10 | |
| "Ghetto Cowboy" | Mo Thugs Family featuring Bone Thugs-N-Harmony | 15 | |
| "Hard Knock Life (Ghetto Anthem)" | Jay-Z | Vol. 2... Hard Knock Life | |
| "Can I Get A..." | Jay-Z featuring Amil & Ja Rule | 19 | |
| "Back That Thang Up" | Juvenile featuring Mannie Fresh & Lil Wayne | 400 Degreez | |
| "I Want It All" | Warren G featuring Mack 10 | I Want It All | 23 |
| "Pushin' Weight" | Ice Cube featuring Mr. Short Khop | War & Peace Vol. 1 (The War Disc) | 26 |
| "Vivrant Thing" | Q-Tip | Amplified | |
| "Jigga My Nigga" | Jay-Z | Ryde or Die Vol. 1 | 28 |
| "Changes" | 2Pac featuring Talent | Greatest Hits | 32 |
| "Got Your Money" | Ol' Dirty Bastard featuring Kelis | Nigga Please | 33 |
| "Everything Is Everything" | Lauryn Hill | The Miseducation of Lauryn Hill | 35 |
| "My Name Is" | Eminem | Slim Shady LP | 36 |
| "Bling Bling" | B.G. featuring Big Tymers & Hot Boys | Chopper City in the Ghetto | 39 |
| "You Got Me" | The Roots featuring Erykah Badu | Things Fall Apart |
| Album | Artist | 1st-week sales | 1st-week position | ||
|---|---|---|---|---|---|
| 1 | ...And Then There Was X | DMX | 698,000 | 1 | |
| 2 | 2001 | Dr. Dre | 516,000 | 2 | |
| 3 | Born Again | The Notorious B.I.G. | 485,000 | 1 | |
| 4 | I Am... | Nas | 470,000 | 1 | |
| 5 | Vol. 3... Life and Times of S. Carter | Jay-Z | 462,000 | 1 | |
| 6 | Still I Rise | 2Pac + Outlawz | 408,000 | 7 | |
| 7 | Tha G-Code | Juvenile | 290,000 | 10 | |
| 8 | The Slim Shady LP | Eminem | 283,000 | 2 | |
| 9 | Blackout! | Method Man & Redman | 254,000 | 3 | |
| 10 | Made Man | Silkk the Shocker | 240,244 | 1 |