The Grammy Award for Best Rap Solo Performance was handed out from 1991 to 2002. Before the introduction of this category a single award was presented for Best Rap Performance. From 2003 to 2004 the award was split into two, Best Female Rap Solo Performance and Best Male Rap Solo Performance. It was returned to the single award in 2005. Eminem and Missy Elliot are the most awarded in the category with 3 wins each.

Winners: Grammys Best Rap Solo Performance

Year
Winner
Song
1991
MC Hammer
"U Can't Touch This"
1992
LL Cool J
"Mama Said Knock You Out"
1993
Sir Mix*a*Lot
"Baby Got Back"
1994
Dr. Dre
"Let Me Ride"
1995
Queen Latifah
"U.N.I.T.Y."
1996
Coolio
"Gangsta's Paradise"
1997
LL Cool J
"Hey Lover"
1998
Will Smith
"Men in Black"
1999
Will Smith
"Gettin' Jiggy wit It"
2000
Eminem
"My Name Is"
2001
Eminem
"The Real Slim Shady"
2002
Missy "Misdemeanor" Elliott
"Get Ur Freak On"
2003
(Best Female Rap Solo Performance) Missy Elliott
"Scream a.k.a. Itchin'"
2003
(Best Male Rap Solo Performance) Nelly
"Hot In Herre"
2004
(Best Female Rap Solo Performance) Missy Elliott
"Work It"
2004
(Best Male Rap Solo Performance) Eminem
"Lose Yourself"
2005
Jay*Z
"99 Problems"
2006
Kanye West
"Gold Digger"
2007
T.I.
"What You Know"
2008
Kanye West
"Stronger"
2009
Lil Wayne
"A Milli"
2010
Jay*Z
"D.O.A. (Death Of Auto*Tune)"