“Remember When” is a rumination on decades of marriage, and it requires a singer with a depth of life experience. As he grew older, Jackson also added new kinds of songs to his repertoire. Even though Jackson had been singing dance songs about infidelity since the beginning of his career, 1997’s “Who Cheatin’ Who” (itself a cover of a 1980 hit by Charly McClain) showed that the form had lost none of its possibility. “Little Bitty” and “It’s Five O’Clock Somewhere” are definitive Jackson: charming and catchy, but heartfelt and never cloying. Even as he grew older, Jackson’s personality and music remained essentially the same. 2 covers Alan Jackson’s singles output between 19, a period that saw him grow from a reliable Nashville hit maker into one of modern country’s elder statesmen.
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