2003 Country Music Association Awards
Jimmy and Alan Jackson won the 2003 CMA for "Vocal Event Of The Year" for "It's Five O'Clock Somewhere."
2003 Academy of Country Music Awards
Then the song won again, for "Single Of The Year" and "Video Of The Year" at the 2003 Academy of Country Music Awards.
2004 Grammy Nomination
In 2004, Jimmy received his first Grammy nomination for "Best Country Collaboration With Vocals" along with Alan Jackson for their #1 hit, "It's Five O'Clock Somewhere."
2004 People's Choice Award
Also, in 2004, Jimmy was nominated for a People’s Choice Award for Favorite Country Male Singer, as well as two Country Music Association Awards (CMAs): Music Video Of The Year for "It's Five O'Clock Somewhere," and Musical Event Of The Year for "Hey Good Lookin'" from his License To Chill CD.
2005 Grammy Nomination
In 2005, Jimmy received his second Grammy nomination: Best Country Collaboration With Vocals for "Hey Good Lookin'" from the License To Chill CD. And there were two other 2005 nominations for "Hey Good Lookin'": Vocal Event Of The Year/Academy of Country Music, and Collaborative Video Of The Year/CMT Music Awards. Also in 2005, there was another CMA nomination - for Musical Event Of The Year for his duet with Martina McBride, “Trip Around The Sun” from the License To Chill CD.