McFerrin won 2 Grammy Awards for Best Jazz Male Vocal Performance ("Another Night In Tunisia" from Spontaneous Inventions) and Best Vocal Arrangement for Two or More Voices ("Another Night In Tunisia" with The Manhatten Transfer).

McFerrin won a Grammy Award for Best Jazz Male Vocal Performance ("'Round Midnight" from the Round Midnight soundtrack).

McFerrin won 2 Grammy Awards for Best Jazz Male Vocal Performance ("What Is This Thing Called Love") and Best Recording For Children (The Elephant's Child with Jack Nicholson).

McFerrin hit #1 for 2 weeks with "Don't Worry, Be Happy."

McFerrin won 4 Grammy Awards for Record of the Year, Song of the Year (songwriter), Best Pop Male Vocal Performance ("Don't Worry, Be Happy"), and Best Jazz Male Vocal Performance ("Brothers"), and was nominated for Album of the Year (Simple Pleasures).

McFerrin was nominated for a Grammy Award for Best Jazz Vocal Performance - Male ("Scrapple From The Apple").

McFerrin won his 10th Grammy Award for Best Jazz Vocal Performance ("'Round Midnight" from Play, a live LP with Chick Corea).