Daryle Singletary: His 10 Essential Songs

Singletary’s first single, and first hit, made the right impression by setting the bar low — thematically speaking, at any rate. Written by Bob McDill and Tommy Rocco, “I’m Living Up to Her Low Expectations” dropped a month before his self-titled debut LP, cracking the country Top 40 as it reached Number 39 in the spring of 1995. From the fluttering opening guitar lick to Singletary’s stone-cold twang, it was built on rock-solid honky-tonking fundamentals. But its real charm came from the lyrics’ carefree self-sabotage, a self-fulfilling prophecy of disappointments assuaged by the boozing and buddies that got him in trouble in the first place. J.G.

If “I’m Living Up to Her Low Expectations” had showcased Singletary’s carousing streak, then its follow-up single, “I Let Her Lie,” showed just how much depth there was to be mined from his smoky Georgia croon. A tear-in-your-beer acoustic ballad penned by Tim Johnson, the track finds Singletary on the flip side of the relationship coin, struggling to forgive an unfaithful lover against his better judgment. The emotional core of “I Let Her Lie” was Singletary himself, as his quivering delivery conveyed shades of hurt and anguish beyond the plainspoken lyrics. It resonated, too, as the song became one of his biggest hits, topping at Number Two. J.G.

After scoring a breakout hit with the heavy emotions of “I Let Her Lie,” Singletary changed course for his follow-up, “Too Much Fun,” showing fans a fully developed good-timing side. Released as the third single from his self-titled debut in 1995, the up-tempo party jam was another winner, reaching the Top Five of Billboard‘s Hot Country Songs chart. Written by Curtis Wright and Jeff Knight, the song showcases Singletary’s crisp, carefree vocal, which outlined a wild night of bar-hopping and howling at the moon – including a memorable opening scene where the song’s protagonist gets busted with 14 buddies in the back of his pickup. C.P.

With the lead single from his sophomore album, All Because of You, Singletary looked back to his gospel roots. Released in 1996, “Amen Kind of Love” featured matter-of-fact lead vocals and a backing choir as Singletary described a romance so fulfilling it could only be heaven sent. But in writing the song, Trey Bruce and Wayne Tester contrasted its soulful, reverent nature with a quick-step tempo, and that combination proved to be a potent one. “Amen Kind of Love” reached Number Two on Billboard’s Hot Country Songs chart, repeating the best showing of Singletary’s career and marking his last appearance in the Top 10. C.P.

The fact that Singletary’s early 1998 single “The Note” barely dented the Top 30 is practically a criminal offense. While Conway Twitty, Tammy Wynette, Doug Supernaw and Gene Watson are among those who cut the song, Singletary’s extraordinary version was touted as a “career record” upon release, perhaps because, in spite of his more youthful voice, he still managed to wring every drop of pathos from the song’s heartbreaking lyrics without ever veering into mawkish territory. Interestingly, “The Note” also earned the singer his first and only Billboard Hot 100 single. S.B. 

Singletary is rightly remembered as a staunch country traditionalist, but one of his most intriguing tracks was actually a cover of a massive, international pop hit. In 2000 he released a version of Australian pop duo Savage Garden’ “I Knew I Loved You,” a silky-smooth ballad that shot to Number One on the Billboard Hot 100 only a year earlier. Singletary’s reading of the song stayed mostly true to the original, but it was little less polished and a lot more organic. And although it was largely overlooked by country fans, it once again illustrated Singletary’s skill with a heartfelt lyric. C.P.

With his naturally resonant vocal timbre and fluid runs, Singletary was an obvious descendent of country’s most distinctive stylists, from George Jones and Merle Haggard to the ultra-smooth croon of Conway Twitty. In 2002, Singletary made those connections even more explicit when he cut Twitty’s 1980 chart-topper “I’d Love to Lay You Down” for his mostly-covers LP That’s Why I Sing This Way, which also featured versions of songs made famous by Buck Owens and Lefty Frizzell, among others. Singletary didn’t do any radical overhauls of Twitty’s hit with his recording, which would peak at Number 43. Then again, he didn’t really need to do anything differently – Singletary’s warm delivery, like a gentle caress atop the song’s unhurried rhythmic stride, sold those romantic promises just as convincingly as consummate loverman Twitty ever did. J.F. 

Singletary’s hit-making days were a thing of the past by the time he released Straight From the Heart in 2007. In fact, it was his second album in a row consisting almost exclusively of covers, but that suited him just fine. “Jesus & Bartenders,” a mournful take on a Larry Cordle and Leslie Satcher deep cut, was a prime example of just how much of a master interpreter Singletary could be when left to his own devices. Now in his mid-thirties, his voice here has grown deeper and duskier, but its end-of-the-line desperation thrives on his direct, uncomplicated expression. J.G.

The stoic, old-school masculinity of Singletary’s persona – however soft its emotional core may have been – meant he was never one to cry over spilled milk. “Spilled Whiskey,” on the other hand, is another matter. Another late-period cut for the Georgian, it appeared on the elegiacally titled There’s Still a Little Country Left, his first new album in six years. Released 20 years on from Daryle Singletary, “Spilled Whiskey” — written by Monty Criswell and Lee Miller — saw him wrestling with the same romantic demons that had sparked “I Let Her Lie.” He may have gotten better at recognizing the warning signs, but that didn’t mean he was any better at avoiding them. J.G.

In his later years, Singletary made the most of a voice that was tailor-made for duets by collaborating with other singers on most of his post-major label albums. The last record to be released during his lifetime, American Grandstand was a collection of duets with bluegrass star Rhonda Vincent, which once again saw him reinterpreting classics and standards. “Louisiana Woman, Mississippi Man” had Singletary tackling Conway Twitty’s role from his 1973 hit with Loretta Lynn, and it was one of Singletary’s most rollicking performances in years. He and Vincent enjoy a playful chemistry, which elicits a joyful howl from the crooner in the song’s final bars, a fitting farewell for one of his final recordings. J.G.