“We Went Just a Little Bit Crazy”: How a Christmas Party Led Kenny Chesney and Brett James to Write ‘Out Last Night'

Some songs are forged through discipline and routine. Others emerge from the foggy aftermath of a holiday hangover.

“Out Last Night” belongs firmly in the latter camp.

Kenny Chesney and Brett James spent nearly two decades as close friends and collaborators, writing more than forty songs together and delivering a string of iconic, fan-favourite country hits, including "When the Sun Goes Down" with Uncle Kracker, "Keg in the Closet", "You Save Me", "Just to Say We Did", and many more.

Yet one songwriting session between the pair stood apart — more unexpected, more memorable, and more special than all the rest.

"I was standing in my kitchen, like at 4:30 in the afternoon on Christmas Eve" James reflected in an in-depth interview with Bruce Wawrzyniak for Now This Entertainment.

"my cell phone rang - it was a flip phone back then. I flipped open the phone and it said 'blocked'."

"The only reason I picked it up was because it said blocked, because in our business if it says unknown you don't pick it up, I'm not going to pick up for anybody on Christmas Eve, but it said blocked, and in our business, at the time, if it said blocked, usually it meant it was somebody famous".

"So I did pick up, and the voice on the other end of the line said, 'Hey Man', and I said, 'Hey man', and he literally said, 'Hey Man', I said 'Hey Man', we did that for a little while, and he finally said, 'what are you doing the day after tomorrow?'"

"Now, it's 4:30 in the afternoon on Christmas Eve, and I have four children under the age of twelve at the time. So of course I said, 'Well, nothing man! What you got in mind?'".

"What he had in mind was more fun than what I had planned. He said 'why don't we go down to the islands and write some songs?'.

Once again, fortunately my four children know where Christmas presents come from in our house, and so 48 hours later I found myself getting on his big fancy jet which takes you to one island, and you land and they put your bags on the big fancy helicopter that takes you right up to the house, which is not the way I ever travel or have ever travelled again by the way.

So we get down there, and it's December 26, it's the day after Christmas, and Nashville is cold and rainy and gets dark at 4:30 that time of year. We set foot on the island, smelt that warm breeze and felt that salt air and he and I, we have a little bit of a reputation for this, we got a little crazy that night.

He got in a little later than I did, anyway long story short, I woke up at his house, got some coffee, grabbed my guitar and went out on his back deck and looked at the prettiest view i'd ever seen for a couple hours. Finally, the sliding glass door to his room opened and Kenny Chesney stuck his head out and said 'Brett, we went out last night'"

"I said, 'Yeah, we did! Maybe that's the song we oughta write today".

"So we started talking and laughing, and a couple hours later we'd written a song called 'Out Last Night', and then we had some lunch, and we wrote a song that afternoon called 'Reality', and both those songs ended up being No. 1"

"All we did was have fun that day, there was no pressure to write a song, there was no pressure to write a hit, there was no pressure to do anything except just enjoy each other's company, make some stuff up and have some laughs".

"That's right up there with my favourite days of my whole life, so I always have to thank Kenny Chesney for that because he made that happen, and he's such a special human being".

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