| Year | Winner | Other nominees | Ref. |
| 1989 | DJ Jazzy Jeff & The Fresh Prince — "Parents Just Don't Understand" | - Ice-T — "Colors"
- Kool Moe Dee — "How Ya Like Me Now"
- MC Hammer — "Turn This Mutha Out"
- Tone Lōc — "Wild Thing"
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| 1990 | MC Hammer — "U Can't Touch This" | - Digital Underground — "The Humpty Dance"
- Biz Markie — "Just a Friend"
- Young MC — "Principal's Office"
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| 1991 | LL Cool J — "Mama Said Knock You Out" | - 3rd Bass — "Pop Goes the Weasel"
- DJ Jazzy Jeff & The Fresh Prince — "Summertime"
- Ice-T — "New Jack Hustler (Nino's Theme)"
- Monie Love — "It's a Shame (My Sister)"
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| 1992 | Arrested Development — "Tennessee" | - Black Sheep — "The Choice Is Yours (Revisited)"
- Kris Kross — "Jump"
- Marky Mark and the Funky Bunch — "Good Vibrations"
- Sir Mix-a-Lot — "Baby Got Back"
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| 1993 | Arrested Development — "People Everyday" | - Digable Planets — "Rebirth of Slick (Cool Like Dat)"
- Dr. Dre — "Nuthin' but a 'G' Thang"
- Naughty by Nature — "Hip Hop Hooray"
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| 1994 | Snoop Doggy Dogg — "Doggy Dogg World" | - Coolio — "Fantastic Voyage"
- Cypress Hill — "Insane in the Brain"
- Dr. Dre — "Let Me Ride"
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| 1995 | Dr. Dre — "Keep Their Heads Ringin'" | - Brandy (featuring MC Lyte, Queen Latifah and Yo-Yo) — "I Wanna Be Down"
- Da Bush Babees — "Remember We"
- Craig Mack — "Flava in Ya Ear"
- Public Enemy — "Give It Up"
- Rappin' 4-Tay (featuring The Spinners) — "I'll Be Around"
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| 1996 | Coolio (featuring L.V.) — "Gangsta's Paradise" | - Bone Thugs-n-Harmony — "Tha Crossroads"
- LL Cool J — "Doin' It"
- 2Pac (featuring Dr. Dre and Roger Troutman) — "California Love"
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| 1997 | The Notorious B.I.G. — "Hypnotize" | - Blackstreet (featuring Dr. Dre) — "No Diggity"
- Dr. Dre — "Been There, Done That"
- Missy Elliott — "The Rain (Supa Dupa Fly)"
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| 1998 | Will Smith — "Gettin' Jiggy wit It" | - Busta Rhymes — "Put Your Hands Where My Eyes Could See"
- Master P (featuring Fiend, Silkk the Shocker, Mia X and Mystikal) — "Make 'Em Say Uhh!"
- The Notorious B.I.G. (featuring Puff Daddy and Mase) — "Mo Money Mo Problems"
- Pras (featuring Ol' Dirty Bastard and Mýa) — "Ghetto Supastar (That Is What You Are)"
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| 1999 | Jay-Z (featuring Ja Rule and Amil) — "Can I Get A..." | - 2Pac — "Changes"
- DMX — "Ruff Ryders' Anthem"
- Nas (featuring Puff Daddy) — "Hate Me Now"
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| 2000 | Dr. Dre (featuring Eminem) — "Forgot About Dre" | - DMX — "Party Up"
- Eminem — "The Real Slim Shady"
- Eve (featuring Faith Evans) — "Love Is Blind"
- Jay-Z (featuring UGK) — "Big Pimpin'"
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| 2001 | Nelly — "Ride wit Me" | - Eminem (featuring Dido) — "Stan"
- Ja Rule (featuring Lil' Mo and Vita) — "Put It on Me"
- Jay-Z — "I Just Wanna Love U (Give It 2 Me)"
- Snoop Dogg (featuring Master P, Nate Dogg, Butch Cassidy and Tha Eastsidaz) — "Lay Low"
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| 2002 | Eminem — "Without Me" | - DMX — "Who We Be"
- Ludacris (featuring Sleepy Brown) — "Saturday (Oooh Oooh!)"
- Nas — "One Mic"
- P. Diddy (featuring Black Rob and Mark Curry) — "Bad Boy for Life"
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| 2003 | 50 Cent — "In da Club" | - 2Pac (featuring Nas) — "Thugz Mansion"
- Eminem — "Lose Yourself"
- Ludacris (featuring Mystikal) — "Move"
- Nas — "I Can"
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| 2004 | Jay-Z — "99 Problems" | - 50 Cent (featuring Snoop Dogg and G-Unit) — "P.I.M.P. (remix)"
- D12 — "My Band"
- Lil Jon and The East Side Boyz (featuring Ying Yang Twins) — "Get Low"
- Ludacris (featuring Shawnna) — "Stand Up"
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| 2005 | Ludacris — "Number One Spot" | - Eminem — "Just Lose It"
- The Game (featuring 50 Cent) — "Hate It or Love It"
- T.I. — "U Don't Know Me"
- Ying Yang Twins — "Wait (The Whisper Song)"
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| 2006 | Chamillionaire (featuring Krayzie Bone) — "Ridin'" | - 50 Cent — "Window Shopper"
- Busta Rhymes (featuring Mary J. Blige, Rah Digga, Missy Elliott, Lloyd Banks, Papoose, and DMX) — "Touch It (Remix)"
- T.I. — "What You Know"
- Yung Joc (featuring Nitti) — "It's Goin' Down"
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