Most modern listeners wouldn’t think anything of drum machines in country music, but when Love, Pain & The Whole Crazy Thing came out in 2006, it was, in its own highly polished way, a daring prospect. Urban understands the form’s bread and butter, and he isn’t afraid to lean into it, whether it’s the folksy pride of “Raise the Barn” or the sentiment of “God Made Woman.” But he also borrows seamlessly from contemporary rock and pop, not just in sound (“Once in a Lifetime”) but in his willingness to lay out big, complicated feelings without getting hung up on what men are allowed to say and how they’re supposed to say it (“Used to the Pain”). Even in its drama, Love... keeps a degree of emotional maturity that makes Urban slightly unusual, or at least triangulates a point between avuncular guys like George Strait and the bro country that came to dominate in the years following. “She never even knew she had a choice/And that’s what happens when the only voice she hears is telling her she can’t,” he sings on “Stupid Boy.” It’s a level of sensitivity that helped Urban stand out in a meaningful way—you’d like him if you were already a Brad Paisley or Carrie Underwood fan, but you could come to him from Coldplay and connect with it just as well. On Love, Pain & The Whole Crazy Thing, he stretches out what we mean when we talk about country music.