George Strait and Jim Lauderdale have plenty of history between them. Since 1992, Strait has cut 14 song penned or co-penned by Lauderdale, including "We Really Shouldn't Be Doing This," his third single from his One Step at a Time album. After the song debuted at No. 72 on Billboard's Hot Country Singles & Tracks chart in May of 1998 thanks to unsolicited airplay, Strait released "We Really Shouldn't Be Doing This" as an official single in September of 1998, and the track peaked in the Top 5 (No. 4).

In 2016, Lauderdale cut "We Really Shouldn't Be Doing This" for his album This Changes Everything, an 11-track project recorded in Austin, Texas, on a short, one-day break in his summer tour schedule. Below, the singer-songwriter recalls for The Boot his memories of writing the hit.

I remember, I was working on -- I had finished my record called Whisper, which came out on RCA [in 1998], and I was renting a room, an apartment, on top of Buddy Miller's house. And Buddy was getting his home studio going, and he sometimes at night -- you know, at two or three in the morning -- I would hear stuff. So I thought, "Look, I want to keep this place, but I'm gonna find some place else that's quiet." So I worked out this great deal with this old hotel here in town called the Union Station -- it used to be an old train station -- and my place was right by the railroad tracks, I could hear the trains going by, I could see the sun set, and it was really just a great place.

And that song idea -- sometimes I really have to labor over [a song], and it's just like tearing out my hair for the songs I write alone -- but that one ... When I get a phrase, sometimes, you know, just that thought, I was just thinking about a conversation with somebody, and so that started coming out. And so I went into the studio I've made a lot of records in and a lot of demos, a place called Moondog here in town, and Tim Coates was the engineer I worked with, and Garry Tallent of the E Street Band, that was his studio.

So I did a demo of the song, and my publisher had been -- they said, "George Strait is comin' up, he's going in" -- they'd been pitching him these songs ... so I took a CD and dropped it by the studio. I thought, I'd just done this, I don't think there's any chance he'll record it, but I have nothing to lose, and I'm discouraged because I'd given him everything I thought he would take, and the next day I found out he liked it.

A lot of times, with the songs, I would intentionally write for him, and I'd feel like "I'm channeling George" ... and those would never get recorded.

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