• 2008 – Entertainer of the Year
• 2007 – Entertainer of the Year
• 2007 – Musical Event of the Year (“Find Out Who Your Friends Are” with Tracy Lawrence and Tim McGraw)
• 2006 – Entertainer of the Year
• 2004 – Entertainer of the Year
• 2004 – Album of the Year as Artist (When The Sun Goes Down)
• 2004 – Album of the Year as Producer (When The Sun Goes Down)

ACM Awards:

• 2008 – Vocal Event of the Year (“Find Out Who Your Friends Are” with Tracy Lawrence and Tim McGraw)
• 2008 – Entertainer of the Year
• 2007 – Entertainer of the Year
• 2006 – Entertainer of the Year
• 2005 – Triple Crown Winner
• 2005 – Entertainer of the Year
• 2004 – Entertainer of the Year
• 2003 – Male Vocalist of the Year
• 2003 – Single Record of the Year as Producer (“The Good Stuff”)
• 2003 – Single Record of the Year as Artist (“The Good Stuff”)
• 1997 – New Male Vocalist of the Year

CMT Music Awards:

• 2007 – Male Video of the Year (“You Save Me”)
• 2006 – Male Video of the Year (“Who You’d Be Today”)
• 2005 – Male Video of the Year (“I Go Back”)
• 2004 – Male Video of the Year (“There Goes My Life”)
• 2004 – Flameworthy Hottest Video of the Year (“No Shoes, No Shirt, No Problems”)
• 2002 – Flameworthy Video of the Year (“Young”)
• 2002 – Flameworthy Male Video of the Year (“Young”)

Other:

• 2009 – Billboard Top Package Award
• 2008 – CMT Online’s Most Digitally Active Male Artist
• 2008 – Country Airplay’s Country Music Artist Of The Year
• 2008 – Billboard Top Package Award
• 2008 – Billboard Eventful Fans’ Choice Award
• 2008 – IEBA Large Venue Artist of The Year
• 2007 – People’s Choice Awards Favorite Male Singer
• 2006 – Billboard Music Awards Best Country Artist
• 2006 – Billboard Music Awards Best Male Country Artist

Nominations:

• 2010 Grammy Best Country Collaboration With Vocals for “Down The Road”
• 2009 Billboard Touring Awards Top Package
• 2009 CMA Entertainer Of The Year
• 2009 CMA Male Vocalist Of The Year
• 2009 CMA Musical Event Of The Year for “Down The Road”
• 2009 CMT Video Of The Year: “Everybody Wants To Go To Heaven” (with the Wailers)
• 2009 CMT Collaborative Video Of The Year: “Everybody Wants To Go To Heaven” (with the Wailers)
• 2009 ACM Entertainer Of The Year
• 2009 ACM Top Male Vocalist
• 2009 ACM Vocal Event Of The Year for “Down The Road” (as an artist)
• 2009 ACM Vocal Event Of The Year for “Down The Road” (as a producer)
• 2008 Grammy Best Country Collaboration With Vocals for “Shiftwork”
• 2008 Billboard Touring Awards Top Package
• 2008 AMA Favorite Male Artist
• 2008 CMA Entertainer of the Year
• 2008 CMA Male Vocalist of the Year
• 2008 CMA Album of the Year “Just Who I Am: Poets and Pirates”
• 2008 CMA Single of the Year “Don’t Blink”
• 2008 CMA Music Video of the Year “Don’t Blink”
• 2008 CMA Musical Event of the Year “Every Other Weekend”
• 2008 CMA Musical Event of the Year “Shiftwork”
• 2008 ACM Top Male Vocalist
• 2008 ACM Album of the Year: Just Who I Am: Poets and Pirates
• 2008 ACM Song of the Year: Don’t Blink
• 2008 ACM Single Record of the Year: Don’t Blink
• 2008 ACM Vocal Event of the Year: Shiftwork
• 2008 ACM Video of the Year: Don’t Blink
• 2008 CMT Video of the Year: Don’t Blink
• 2008 CMT Male Video of the Year: Don’t Blink
• 2008 CMT Tearjerker Video of the Year: Don’t Blink
• 2008 PCA Favorite Country Song: Never Wanted Nothing More
• 2007 CMT Video of the Year: You Save Me
• 2007 ACM Top Male Vocalist
• 2007 CMA Music Video of the Year: You Save Me
• 2007 CMA Male Vocalist of the Year
• 2006 BMA Best Country Album: The Road and the Radio
• 2006 BMA Best Country Song: Summertime
• 2006 AMA Best Male Country Artist
• 2006 CMA Single of the Year: Summertime
• 2006 CMA Album of the Year: The Road and the Radio
• 2006 CMA Male Vocalist of the Year
• 2006 ACM Top Male Vocalist
• 2006 CMT Video of the Year: Who You Be Today
• 2005 CMT Video of the Year: I Go Back
• 2005 CMT Hottest Video of the Year: Old Blue Chair
• 2005 CMT Collabortive Video of the Year: Hey Good Lookin
• 2005 ACM Vocal Event of the Year: When the Sun Goes Down
• 2005 ACM Album of the Year: When the Sun Goes Down
• 2005 ACM Top Male Vocalist
• 2005 CMA Male Vocalist of the Year
• 2005 CMA Entertainer of the Year
• 2005 AMA Best Male Country Artist
• 2004 CMT Video of the Year: There Goes My Life
• 2004 ACM Song of the Year: There Goes My Life
• 2004 ACM Top Male Vocalist
• 2004 ACM Entertainer of the Year
• 2004 CMA Musical Event of the Year: Hey Good Lookin
• 2004 CMA Musical Event of the Year: When the Sun Goes Down
• 2004 CMA Male Vocalist of the Year
• 2004 AMA Best Male Country Artist
• 2003 CMT Hottest Video of the Year: The Good Stuff
• 2003 CMT Male Video of the Year: The Good Stuff
• 2003 CMT Video of the Year: The Good Stuff
• 2003 ACM Song of the Year: A lot of Things Different
• 2003 ACM Album of the Year: No Shoes, No Shirt, No Problems
• 2003 ACM Entertainer of the Year
• 2003 CMA Male Vocalist of the Year
• 2003 CMA Entertainer of the Year
• 2002 ACM Top Male Vocalist
• 2002 CMA Album of the Year: No Shows, No Shirt, No Problems
• 2002 CMA Male Vocalist of the Year
• 2001 ACM Top Male Vocalist
• 2000 ACM Top Male Vocalist
• 1999 CMA Music Video of the Year: How Forever Feels
• 1999 CMA Horizon Award