The Andie Summers Show

NASHVILLE, TN - JUNE 10: Kenny Chesney performs onstage during the 2015 CMT Music awards at the Bridgestone Arena on June 10, 2015 in Nashville, Tennessee. (Photo by Erika Goldring/Getty Images for CMT)

Kenny Chesney is a country music legend who’s been entertaining fans for over 25 years. His “No Shoes, No Shirt, No Problem” lifestyle is something every American strives to live, which makes a Kenny Chesney playlist necessary on everyone’s phone.

His fans range from all ages because he sings about everyday life, love, and loss. One of the defining qualities of Chesney’s music is its ability to transport listeners to idyllic, sun-kissed landscapes and beachside serenity. If your friend is a Kenny Chesney fan, keep them close, they’re a good person.

Kenny Chesney Tailgates 

Kenny Chesney PLaylist - Singer/Songwriter Kenny Chesney performs during Kenny Chesney's No Shoes Nation

Kenny Chesney fans are some of the most loyal and passionate fans in the world. They are a testament to Chesney’s talent and his ability to connect with people through his music. 

Every other year or so, Chesney hits the states on a nationwide tour around the U.S. When he’s not performing on beaches or at festivals, he’s selling out football stadiums across the country.

The tailgates are like none other. Members of “No Shoes Nation” will wake up early and prepare for the fun, “Chesney-filled” day ahead of them.

They’ll pack a cooler of beer and prepare sandwiches, dips, and snacks for a long day of tailgating. Even in a parking lot party, you can always find the beach or a makeshift version of it.

There’s always one tailgater who fills up their truck with sand to spill on the asphalt and a blow-up pool to cool everyone down. If you’ve never been to see Kenny Chesney live in concert, the tailgate before the show is an experience in itself.

Let’s pretend that we’re on a beach without a worry in the world and an Island Girl drink in our hand. Take a look at the top Kenny Chesney songs, it might warm you up while we begin to enter the winter season!

The Ultimate Kenny Chesney Playlist: His Most Iconic Songs

Kenny Chesney Playlist- Singer-songwriter Kenny Chesney performs onstage during the 4th ACM Party For A Cause Festival

  • "Don't Blink"

    “Don’t blink, just like that you’re six years oldAnd you take a napAnd you wake up and you’re twenty-fiveAnd your high school sweetheart becomes your wife”

  • "No Shoes, No Shirt, No Problems"

    “Want a towel or a chair, in the sand by the seaWanna look through my shades, and see you there with meWanna soak up life for a while, and lay back lowNo boss no clock no stress, no dress code”

  • "The Boys of Fall"

    “Well, it’s turn and face the Stars and StripesIt’s fighting back them butterfliesIt’s call it in the air, alright, yes sir, we want the ballAnd it’s knocking heads and talking trash”

  • "I Go Back"

    “An’ I go back to a two toned short bed ChevyDrivin’ my first love out to the levyLivin’ life with no sense of timeAn’ I go back to the feel of a 50-yard line”

  • "Knowing You"

    “But God, we were so aliveI was a kid on a carnival rideHoldin’ my breath ’til the momentWhen you were gonna leave me too soon”

  • "All The Pretty Girls"

    “I’m coming over, call all your friends“Somebody hold me”, all the pretty girls saidAll of the whiskey went to my head“Shut up and kiss me”, all the pretty girls said”

  • "How Forever Feels"

    “Big orange ball, sinking in the waterToes in the sand, couldn’t get much hotterLittle umbrella shaped margaritasCoconut oil, tanning señoritas”

  • "Living In Fast-Forward"

    “‘Cause I’ve been livin’ in fast forwardHillbilly rock star out of controlI’ve been livin’ in fast-forwardNow I need to rewind real slow”

  • "Beer In Mexico"

    “So I’ll just sit right here and have another beer in MexicoDo my best to waste another daySit right here and have another beer in MexicoLet the warm air melt these blues away”

  • "She Thinks My Tractor's Sexy"

    She thinks my tractor’s sexyIt really turns her onShe’s always starin’ at meWhile I’m chuggin’ along”

  • "We Do"

    “We come down from the mountains, come up from the coastWe’re all comin’ out of some kinda comatoseFill up our cups with a little bit of freedomCome on, hold ’em up, everybody, let me see ’em”

  • "You Had Me From Hello"

    “Well, you had me from “Hello”And I felt love start to growThe moment that I looked into your eyes, you won meIt was over from the start”

  • "Here and Now"

    “Here and nowEverybody’s waitin’, but they’re waiting on whatBetter get to livin’, ’cause all we’ve got isHere and now”

  • "Anything But Mine"

    “And in the morning I’m leaving, making my way back to ClevelandSo tonight I hope that I will do just fineAnd I don’t see how you could ever beAnything but mine”

  • "The Good Stuff"

    “Not a soul around but the old bar keepDown at the end an’ looking half asleepBut he walked up, an’ said, “What’ll it be?”I said, “The good stuff”

  • "Get Along"

    “Get along, on down the roadWe’ve got a long, long way to goScared to live, scared to dieWe ain’t perfect but we try”

  • "Summertime"

    “Perfect song on the radioSing along ’cause it’s one we knowIt’s a smile, it’s a kissIt’s a sip of wine, it’s summertimeSweet summertime”

  • "There Goes My Life"

    “And he said, “There goes my lifeThere goes my future, my everythingMight as well kiss it all goodbyeThere goes my life”

  • "She's Got It All"

    “All my life I spent-a-hopin’I could give someone such devotionEvery sweet memory I can recallShe got it all”

  • "When The Sun Goes Down"

    “Cause when the sun goes down we’ll be groovin’When the sun goes down we’ll feel alrightWhen the sun sinks down over the waterEverything gets hotter when the sun goes down, yeah”

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