David Lee told The Boot
the story of this song, which he penned with Tony Lane and Johnny Park around 2000. "Johnny needed songs for his record that were commercially viable, so we were actually going to write for his record. At the time he had a record deal with Sony. I went in with the title. And being a Texas boy, I'm always looking for things George Strait would say. 'Roll With It' sounded like something George would say. This just popped in my head one day, driving around. I figured if Johnny didn't cut it, I wanted to try and make it something George Strait would hear -- a middle of the road country song with a good message and good feel.
The groove and melody of the song came to us first. It was one of those songs that was really quick to write. Usually it'll take a few sessions. I had the title coming in, but it was very give-and-take when we started coming up with lyrics, where as a writer you'll say something and the next guy will say something, and before you know it, you're just rolling, and it just starts coming out. I remember saying something about a guitar and fishing pole, and then Tony came in and said something about, 'Baby, fill that cooler full of something cold …' It wasn't like someone had an epiphany moment where they went, 'Oh! This is it!' I just remember we were all sitting there talking about what Johnny wanted to do for his record, and try and keep it in the middle. We were all on the same page.
Johnny didn't end up cutting it, but Kevin Denney recorded it for his record ... but then he lost his record deal. Thank God for the Cross Weavers and Carson Chamberlains of the world, though. Cross was the song plugger at Warner/Chappell, and he kept 'Roll With It' in his pocket all those years ... because he believed in it.
It's amazing that this song was recorded after all those years. And there's a bunch of these kind of songs, just laying around in these catalogs in Nashville. There's guys in this town that write everyday, and there's a bunch of great songs that get buried in these catalogs. But these publishers, a lot of times they'll want the new song that you just wrote that week. Most songs aren't pitched but a handful of times after you write them. They're played for other people. If they land in the hands of a plugger or an A&R guy who absolutely loved it, and he keeps it in his repertoire stuff to play for other artists ... then they just get lost.
But 'Roll With It' found a way to just keep rollin'! (laughs) I always thought this song was a hit from the beginning. I always believed it was a radio sounding thing. It just had a feel about it. Most songs I write, I write for George Strait. I figure if George doesn't cut it, somebody else is gonna want to do it.
That's what you think about, being a writer -- because George being the King of Country Music, tends to know the marketplace ... and knows the people he's singing to. And if George will sing it, a lot of other people will, too.
So this song always stayed in my head, and it was always a song that I believed, one day would get cut. And it did! Kevin Denney cut it, and Carson Chamberlain tried to cut it on Billy Currington. And Carson just kept it. And then Easton came along ... and thank God he did, because he did a wonderful job on it.
Easton and George are two different people. Easton is a great guy and great singer, and I thank God that Carson kept that song around, and that Cross -- the song plugger over at Warner/Chappell -- he loved the song so much, he pitched it to another company ... even though he had nothing to gain from it."