Black has been nominated for 4 Grammy Awards for best Country Male Vocal Performance (1990 - "Killin' Time", 1997 - "Like the Rain", 1998 - "Something That We Do", 1999 - "Nothin' but the Taillights"), he was also nominated for 6 Grammy Awards with 1 win in the category of Best Country Collaboration with Vocals - "Hold On Partner" in 1991 (w/ Roy Rogers), "A Bad Goodbye" in 1993 (w/ Wynonna), "Still Holding On" in 1997 (w/ Martina McBride), "Same Old Train" in 1998 which got the Grammy Award (with Joe Diffie, Merle Haggard, Emmylou Harris, Alison Krauss, Patty Loveless, Earl Scruggs, Ricky Skaggs, Marty Stuart, Pam Tillis, Randy Travis, Travis Tritt & Dwight Yoakam), "When I Said I Do" in 1999 (w/ wife Lisa Hartman Black), and "Hey Good Lookin'" in 2004 (Jimmy Buffett, Kenny Chesney, Alan Jackson, Toby Keith, and George Strait).