Your Top 10 Kenny Chesney Songs

Can you pick your top 10 Kenny Chesney songs? Tough job to be sure.

I got a great email last week from a Castaway named Ryan E., right off the bat I knew I already liked this guy. We Ryan’s have to stick together! He told me that he lives in the land locked city of Nashville and is pondering a move to live by the sea in sunny Florida. Stop me if you’ve heard this story before. At the end of his email he hit me with a rather tough question,

And oh yes, what would your top 10 Kenny Chesney songs be?

I sat back in my chair and thought about that for a minute. I’m not sure if I’ve ever tried to figure out my top 10 Chesney songs. Would it even be possible? How can one choose one great song over another? Depending on mood, some songs ring higher at certain times. This was going to be a challenge, but challenge accepted.

I clicked over to iTunes and started going through the albums and all the songs. It took awhile narrow it down and made me sick to leave some off the list, but this is what I came up with.

RSR’s Top Ten Kenny Chesney Songs

  • Be As You Are
  • Anything But Mine
  • Out Last Night
  • You And Tequila
  • Boats
  • Beer In Mexico
  • Somewhere In The Sun
  • Soul Of A Sailor
  • Old Blue Chair
  • Island Boy

Honorable Mention to Magic.

These are the songs I selected when I wrote Ryan back. Now these may change depending on mood, but all-in-all these these are the top 10 I will stand by. As you can see just about all of them are part of Kenny’s island collection. Anything But Mine and You And Tequila are more love songs than having to do with the island lifestyle, but they really connect and have history, so I tossed them on the list. I’m starting to sound a little sappy and sensitive, so I’m going to turn it over to you guys.

In the comment section below, list your top 10 Kenny Chesney songs. It’s going to be tough but give it a try! Looking forward to seeing what you guys like.


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By |2016-12-31T11:58:40-04:00March 25th, 2012|Kenny Chesney, Salt Life Sound (Music)|20 Comments

About the Author:

Just a salty pirate looking to explore and document the wonders of the Caribbean. Professional blogger, rum judge, consultant, marketer, and consumer of blue water beauty.


  1. dj March 26, 2012 at 9:56 am

    When The Sun Goes Down has to be on the list!

  2. Heather March 26, 2012 at 10:10 am

    I was looking for a way to NOT stop work. You have given me an excuse to peruse my iTunes and listen to my favorite music. This is almost ridiculously hard. It may change before lunch.

    Somewhere in the Sun — I call my best friend “Ivan” because of this song. When she moves to the islands in a couple of years it will be even more appropriate.
    Spirit of a Storm — it’s a dark song, but there is such a beauty about it, and something recognizable.
    Old Blue Chair — Comfort food for the ears and soul.
    Reality — it’s like an excuse to fantasize about what you really want to do with your life, and maybe take the chance…
    You and Tequila — I just like it. That’s it.
    I’m Alive — the ideal song to listen to to remind me of how good life really is. Even in Kansas City in winter.
    Out last Night — jumped to the top after a particular Carnival night in New Orleans…..
    Flip Flop Summer — defines to me the start of the best time of year. It’s like my version of a Christmas carol.
    Boys of Fall– I’m a football mom, so i can’t help it. This song makes me unbelievably sappy.

  3. Heather March 26, 2012 at 10:12 am

    Not START work. Lord. Mondays.

    And Magic… I love that song 🙂 For some reason when I listen to it it makes me think about dancing on the beach… that certain big band style reminiscent of the bands that used to play in dance halls and ampitheatres, music spilling out into the summer night air.

  4. mm
    RumShopRyan March 26, 2012 at 10:24 am

    Great list Heather! I’m might have to add another honorable mention: Can’t believe I left Flip Flop Summer off! Nearly impossible to pick just ten!

  5. Chris March 26, 2012 at 11:18 am

    Good thing you didn’t ask for an Elite Eight. It was certainly tough to pick just 10! Here they are in purely random order… The list may change when Kenny’s new CD is released on June 19th!

    Something Sexy About The Rain
    Anything But Mine
    You and Tequila
    She Thinks My Tractor’s Sexy
    No Shoes, No Shirt, No Problems
    Beer In Mexio
    Outta Here

  6. The Shell Princess March 26, 2012 at 2:21 pm

    I’m sending the Sisters of the Sun over to here to leave their lists. I put mine on your facebook page Come join our group Ryan!

  7. KeyWestDan March 26, 2012 at 6:55 pm

    OK I’ll give you my top ten but I agree how can you just have ten?

    1 Island Boy
    2 Be as you are
    3 Boats
    4 Boston
    5 Summertime
    6 Brandy
    7 In this boat alone
    8 Out Last Night
    9 Blue rocking chair
    10 There goes my life

    and 30 more….

  8. Phyllis March 26, 2012 at 8:18 pm

    1. Anything But Mine
    2. You and Tequila
    3. Something Sexy About the Rain
    4. Boys of Fall
    5. No Shoes, No Shirt, No Problems
    6. You Save Me
    7. One Step Up
    8. Reality
    9. Out Last Night
    10. She Thinks My Tractors Sexy

  9. Big Kahuna March 27, 2012 at 12:38 am

    Easy #1- you and tequila,
    Then in no pert ocular order:
    Beer in Mexico
    Island boy
    Where I come from
    Out last night
    Live those songs
    No shoes,ns,np
    Ten with a two

    Then the rest of the good ones, followed by three or 4 I just don’t like.

    Good post Ryan! Way to illicit a response from us castaways!


  10. mm
    RumShopRyan March 27, 2012 at 9:52 am

    Thanks Big Kahuna. Good list by the way. Cheers!

  11. Christine Morse March 27, 2012 at 11:31 am

    1. Keg in the Closet
    2. Old Blue Chair
    3. Coastal (This is slowly climbing to the top of my list)
    4. Nowhere to Go, Nowhere to be
    5. Boats
    6. Guitars and Tiki Bars
    7. Key’s in the Conch Shell
    8. Soul of a Sailor
    9.French Kissing Life
    10. Something Sexy about the Rain

    His Be As You Are CD though is one of only 2 CD’s that I can listen to from beginning to end without skipping songs…It makes me so happy, while I was deployed it was pretty much the only thing I listened to and even after 5 months of non-stop I can’t get enough…

  12. James Losinger March 27, 2012 at 1:54 pm

    Can’t believe no one mentioned the song “The Life”. The words almost make me quit work every time I hear it.

  13. Christine Morse March 27, 2012 at 1:58 pm

    James, you are so right about that song. It has been one of those years where I wish I had the option of quitting and just moving down to Florida whether my husband wants to or not. 🙂

  14. Joshua Hoffman March 27, 2012 at 6:10 pm

    1.) Guitars and Tiki Bars
    2.) Key Lime Pie
    3.) Key’s In The Conch Shell
    4.) Coastal
    5.) You and Tequila
    6.) No Shirt, No Shoes, No Problem
    7.) Beer in Mexico

    : )

  15. Matt March 27, 2012 at 10:01 pm

    1.) Summertime…
    2.) Flip Flop Summer…
    3.) Island Boy…
    4.) Be As You Are…
    5.) In This Boat Alone…
    6.) Way Down Here…
    7.) On The Coast of Somewhere Beautiful
    8.) Beer In Mexico
    9.) Something Sexy About The Rain
    10.) Nowhere To Go, Nowhere To Be

  16. RP in Philly March 27, 2012 at 11:13 pm


    Every so often I take a peek at your blog. Helps me through long hours at work. Great job and keep it up ;).

    Naming the top ten from the island cowboy is almost impossible. You are right, its where your at right now. If you asked me tomorrow, I would have a different ten.

    Here goes:
    1 Out Last Night
    2 Island Boy
    3 Boston
    4 You and Tequila
    5 Be as You Are
    6 Summertime
    7 The Life
    8 No Shoes, No Shirt….
    9 Flip Flop Summer
    10 One Step Up (One of the Best Cover Ever)

    I could go on and on….

  17. Sarah April 9, 2012 at 9:44 pm

    This is really tough, but these are my top ten at the moment. Could easily change tommorrow though because I like so many of Kenny’s songs!

    In no particular order:

    1. Ain’t Back Yet
    2. How Forever Feels
    3. Don’t Happen Twice
    4. Out Last Night
    5. Old Blue Chair
    6. Be As You Are
    7. Coastal
    8. The Woman With You
    9. On the Coast of Somewhere Beautiful
    10.Keg in the Closet

  18. mm
    RumShopRyan April 10, 2012 at 6:11 am

    Good list Sarah! I do live Ain’t Back Yet. Cheers!

  19. Austin October 19, 2012 at 3:46 pm

    A little late, I know, but I just HAD to share this list.
    I have loved KC since I first heard him back in the early 90’s. But ever since “When the Sun” I have put Kenny at the top of my list of artists, here he will stay until… Well, until he retires, and then, probably long after.
    My favorte KC songs are:

    1 – Old Bird Dog (From the limited edition of Road and the Radio)
    2 – Anything But Mine (Reminds me of summers at the Jersey Shore… The REAL one.)
    3 – Better As A Memory (Lovin’ KC sigin’ Carusoe!)
    4 – Old Blue Chair (Ocean Mix)
    5 – Freedom
    6 – The Road and the Radio
    7 – Just Not Today
    8 – Makes Me Wonder (Kudos for the new track making it into my top 10)
    9 – Seven Days – (Reminds me so much of Anything But Mine)
    10- Sherry’s Living in Paradise

    Honerable mention to “Boston.” Would have made the top 10, if she wasn’t wearing a Red Sox cap. I’m a Yankees fan.

  20. ass March 9, 2013 at 11:03 am

    i love kenny

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