In 1998, Alan Jackson and his wife of twenty years separated for several months. It’s no surprise, then, that the feeling of regret on High Mileage runs deep. The album’s standout tracks are sung from the point of view of someone who is on the verge of losing everything he loves. In “Hurtin’ Comes Easy” Jackson sings, “I've spent a lifetime lookin' for love / Just when I find it, it comes undone.” “Gone Crazy” shows a man tortured by his loneliness. Most revealing of all is the album’s centerpiece, “What A Day Yesterday Was,” which watches a couple flipping through old scrapbooks, as Jackson sings the refrain: “If forever should end today / And there's no tomorrow for us / What a day yesterday was.” The heartbreak inherent in High Mileage doesn’t keep it from being an excellent listen. Jackson’s pain is couched in the rich and easygoing playing of his backing band. Still, the album gets its depth from the personal subtext, and the steadfast avowals of “I’ll Go On Loving You” and “Amarillo” leave lasting impressions on the listener.