Songfacts®:

• The lead single from Kenny Chesney's sixteenth studio album was written by David Lee Murphy and Ross Copperman. According to Chesney, it is an anthem that rebels against the mundane "9-to-5." "No matter how you live, there is that part of you that yearns to be free, to say, 'What the hell...' and just do what you want to do! That's what this song is all about," he explained. "You can just say, "Enough,' even if it's only in your mind, while you're watching your boss' mouth move and are dreaming of whatever gets you off ... You can fly your pirate flag in your head, tack it up behind your computer at work, tattoo it under your skin - and no one has to know."
• A previous Chesney single with a similar theme of getting off your boat and enjoying life was his 2011 country chart-topper "Live a Little." David Lee Murphy also co-penned that tune.
• Directed by Shaun Silva, the song's music video is an ode to a carefree day. Chesney told The Boot that the beautiful women seen in the clip aren't models from a casting agency: "What people might not realize about a lot of the 'babes' in this video is those are my friends, girls I know from the island who did the very thing this song is about," he explained, "and that freedom from what's expected just makes them shine. I think there's a little bit of 'Ferris Bueller' in all of us, and this song is all about who we'd be on a perfect day where we just said, 'Forget about it!' So, that's what we tried to capture."
• David Lee Murphy told Roughstock about the writing of the song. "I was over at Ross' house, and we were just sitting there playing ... goofing around," he recalled. "He had a little groove for a song. He started playing it ... like a mandolin thing. I thought, man, that's cool! It was just different. It sounded like pirate music to me. I was just thinking about it, and I had this title, 'Pirate Flag.' I knew Kenny was on the verge of getting ready to cut. It just made sense to put my idea with his music because it sounded like pirate music. When that title popped into my head, I said what about this, and Ross started messing around with it. We just kind of put it together. Soon enough, we had a 'pirate flag and an island girl.'"
  
  "They sent it to Kenny, and Kenny liked it," added Murphy. "It just sounded like Kenny to me … just like him. But there are a lot of times - like when Ben Hayslip and I wrote 'The Only Way I Know' (Jason Aldean) - there are just certain artists you hear songs for... you go, this would be perfect for this guy. This one sounded just right for Kenny."
• Chesney explained the song's meaning to Billboard magazine: "I think there's a side to all of us that gets caught up in our day-to-day life, drive down the same road to work, hit the same bumps, no matter how old they are or whatever, and you can have this anxiety or mundane existence or boredom," he said." I have those emotions, too. 'Pirate Flag' is about it's OK to check out from all of that. People have different ways of raising the pirate flag and checking out. Some people come to our shows, some people use music, some people go to the lake, some people do whatever, exercise, but it's that idea of rebelling against whatever it is that's weighing you down."