Introduction
When Dean Martin recorded his version of “Crying Time,” he brought something unique to the classic tearjerker: effortless charm and velvet sincerity. Originally written and recorded by Buck Owens in 1964—and famously turned into a Grammy-winning hit by Ray Charles—“Crying Time” is a song about that quiet heartbreak just before goodbye. And in Dean’s hands, it becomes something smooth, wistful, and gently aching.
Known for his laid-back delivery and crooner’s touch, Dean Martin doesn’t overplay the sorrow in this track. Instead, he eases into it—letting the sadness settle softly, like a late-night drink poured slow. His voice glides over the melody with warmth and ease, but there’s a hint of resignation beneath the surface. A kind of sadness he doesn’t shout about—but you can feel it all the same.
What makes Dean’s version so compelling is that balance. He doesn’t wallow. He doesn’t plead. He simply accepts the heartache with grace, giving the song a mature, bittersweet tone that resonates even more as time passes. The arrangement is classic Dean—gentle rhythm, soft strings, and that unmistakable voice floating above it all like a sigh you didn’t know you were holding.
For fans of traditional pop and country crossovers, “Crying Time” stands as a reminder of how Dean Martin could take even the saddest lyric and make it feel like a companion—not something to grieve, but something to understand.
It’s the kind of song you play when the lights are low, the memories are close, and all you want is a voice that makes even heartache sound beautiful.