Sometimes all you have to do is ask, or rather, keep asking—and asking, and asking. This month’s issue is a special one for all of us at Texas Monthly. Gazing out from the cover of the magazine is a striking new portrait (by the photographer Joe Pugliese) of the greatest country singer ever to come out of Texas, the man with more number one hits than any other recording artist in music history, a beloved icon to millions and millions of Texans, and one of the hardest “gets” in our business: the incomparable George Strait. 

It’s been 21 years since we last put Strait on the cover, a drought that was not for lack of trying. As any longtime fan of his knows, Strait is famously press-shy. He rarely participates in magazine profiles or sits for photo shoots. This is not because he’s rude or ungenerous; it’s just that he’s naturally disinclined to overexposure. He keeps his private life as private as he can. Over the years, so many of our requests have been politely but firmly declined that he’s almost attained mythical status—our own version of Moby Dick or the Loch Ness Monster.

In 2012, when it was announced that Strait would be retiring from touring, we began to consider how we might break this losing streak. Strait’s last tour would be a very big deal, and we couldn’t bear the thought that the moment might pass without a Texas Monthly cover to mark it. We figured that the usual approach would probably have the usual outcome, so rather than send off a formal request, we enlisted the two biggest Strait fans on staff—senior editor John Spong and creative director T. J. Tucker—to cook up some specific cover ideas. We knew that whatever they came up with would be more or less what Strait’s fans would want to see, an image that felt true to the relationship between the man and his adoring audience. 

Throughout 2013, as the Cowboy Rides Away Tour rode along, with its June 2014 finale on the horizon, we batted around various concepts, none quite good enough to pitch to the Strait camp. Finally, John and T.J. went to one of the shows. The next morning, T.J. was in my office. “You know how Strait does that thing at the end of the concert where he puts his hand over his heart?” he said. “That’s the cover.” He laid it out in a long and impassioned email to Strait’s management, and, for the first time since 1993, they agreed to let us take his picture (though not to interview him). It helped that T.J., who grew up on a ranch outside Abilene, understands the world of Strait’s music a whole lot better than your average magazine creative director. In time, Strait’s management came to trust him.

The shoot took place about a month ago, before a show in Tulsa; Strait was as humble and charming as anyone we’ve ever photographed. The result is one of the most memorable cover portraits in the history of Texas Monthly. And one that was absolutely worth the wait. Sometimes, all you have to do is keep asking.