Daryle Singletary was born March 10, 1971, in Cairo, Georgia. His father, Roger Singletary, was a postal worker, while his mother, Anita, was a hairdresser. At an early age, he sang Gospel Music with his cousins and brother. Later on, in high school, he began taking vocal classes as well. In 1990, he moved to Nashville, Tennessee, in pursuit of a record deal.
In Nashville, he found work singing during open-mic nights at various venues, before finding work as a demo singer. One of the demos that Singletary sang was “An Old Pair of Shoes”, which Randy Travis eventually recorded. Travis recommended Singletary to his management team, who helped him sign to a recording contract with Giant Records.
Singletary’s self-titled debut album was released in 1995. The lead-off single, “I’m Living Up to Her Low Expectations”, spent one week in the Top 40 on the Billboard Country charts, peaking at No. 39. It was followed by his biggest hit, the No. 2 “I Let Her Lie”. This album also produced the No. 4 “Too Much Fun” and finally “Working It Out” at No. 50. Despite the two Top Five hits it produced, the album sold poorly and reached No. 44 on Top Country Albums. The album was produced by David Malloy, James Stroud and Randy Travis.
In 2000, Singletary signed to Audium/Koch Entertainment to release his fourth album, 2000’s Now and Again. This album’s lead-off single was a cover of Savage Garden’s 1999 pop single “I Knew I Loved You”. After Audium/Koch closed its Country division, Singletary signed to Shanachie Records. His first project for the label was a second album, 2007’s Straight from the Heart, which was also largely composed of cover songs. Its singles, “I Still Sing This Way” and “Jesus & Bartenders.”
In 2009, Singletary returned to Koch under the label’s new name of E1 Music. He released his next single, “Love You With the Lights On” in February. The single was the lead-off single to a new album, Rockin’ in the Country, released in June 2009.
Singletary died unexpectedly at his home in Lebanon, Tennessee, on the morning of February 12, 2018. The cause of death was not revealed.
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