For me, it seems to start in 2005. Very gradually at first. With "Beer in Mexico" from his "The Road and The Radio" album you are starting to see the melancholy side of Kenny. It still has a very upbeat, almost island tempo but if you listen to the words, they are a little bit deeper than his norm.
It wasn't until 2008 that I heard something from him that completely surprised me. It was "Better as a Memory" from his "Poets and Pirates" album. Not a lot of people liked this song, perhaps because it was such a shift from what he usually does. Around this time I heard a radio interview with Kenny regarding this song at which time he said he wanted to roll the dice on this song. People were either going to love it or hate it but he liked the song so much he wanted to take a chance on it. I for one think the gamble paid off (the song did hit #1 in 2008).
Cut to now (or 2010). There have been a couple of his new songs out recently that I think are brilliant. Both are from his latest album "Hemingway's Whiskey". The first one is "Somewhere with You". It's a beautiful, moody, dark song. There was a time in my life I felt the exact same way and I think that is why this song speaks to me so loudly. Those times are long gone but I still find this song haunting. The first time I heard it I thought, "How does he do that?". The second song is "You and Tequila" which has been playing on the radio since Memorial Day. Again, wow Kenny! You are growing up! This song is a duet with Grace Potter and their harmonizing on this song is sublime. I do recommend downloading the radio version however as I saw them perform this song live on the "Today" show and it did not do the song justice.
Kudos Kenny! This is one fan that continues to grow more satisfied over time!
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