Grammy Awards:
- Best Jazz Vocal Album: Dedicated to You
Grammy Nominations:
- Best Jazz Vocal Album: Nightmoves
- Best Jazz Vocal Album: Man in the Air
- Best Jazz Vocal Album: Flirting With Twilight
- Best Jazz Vocal Album: Live in Chicago
- Best Jazz Vocal Performance: This Time It's Love
- Best Jazz Vocal Performance: The Messenger
- Best Jazz Vocal Performance: Close Your Eyes
- Best Instrumental Arrangement Accompanying a Vocalist
"Dedicated to You" from Dedicated to You
(Arrangement by Laurence Hobgood)
- Best Instrumental Arrangement Accompanying a Vocalist
"Easy Living" from Flirting With Twilight
(Arrangement by Kurt Elling and Laurence Hobgood)
DownBeat :
- Critics Poll Winner: Male Vocalist of the Year -- 2000, 2001, 2002, 2003, 2004, 2005, 2006, 2007, 2008, 2009, 2010
- Critics Poll Winner: Talent Deserving Wider Recognition -- 1997, 1998, 1999, 2000
- Readers Poll Winner: Male Vocalist of the Year -- 2002, 2004, 2006, 2008, 2009
JazzTimes :
- Readers Poll: Male Vocalist of the Year -- 1998, 2000, 2001, 2002, 2008
Jazz Journalists Association :
- Male Singer of the Year -- 2000, 2002, 2006, 2007, 2009, 2010
JazzWeek :
- Vocalist of the Year -- 2006
Académie du Jazz de Paris :
- Prix Billie Holiday: The Messenger
Nightlife Awards:
- Outstanding Jazz Vocalist in a Major Engagement -- 2010
Chicago Music Awards :
- Jazz Record of the Year -- 1997
Rockford Area Music Awards :
- Hall Of Fame Induction -- 2000
Chicago Tribune :
- A Chicagoan of The Year (Arts) -- 1995
Crain's Chicago Business :
- Inductee: 40 under 40 (Who Make a Difference in Chicago Business) -- 1998
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