In 2000, Singletary switched to Audium Entertainment (a division of Koch Entertainment), where he released the albums Now and Again (2000) and That's Why I Sing This Way (2002), both of which were largely composed of cover songs. A third album of covers, 2007's Straight from the Heart, was issued on the independent Shanachie Records label. He returned to Koch (now renamed E1 Music) in 2010, to release Rockin' in the Country.
Daryle Singletary was born March 10, 1971 in Cairo, Georgia. His father was a postal worker and his mother was a hair dresser. 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. By the early 1990s, he had 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.
A second album for Giant, All Because of You, was released in 1996. Although its lead-off single "Amen Kind of Love" became his second No. 2 hit that year, the album's other two tracks — "The Used to Be's" and "Even the Wind" — both fell short of Top 40, peaking at number 48 and 68 respectively.
Ain't It the Truth, his third and final album for Giant, produced a minor hit in "The Note", which peaked at No. 28 on the country charts and No. 90 on the Billboard Hot 100. Despite this song's minor crossover success, however, this album also saw its second and third singles miss the Top 40, and Singletary was dropped from Giant's roster.
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". Following it were "I've Thought of Everything" at No. 70, and the album's title track, which failed to chart.
His second album for Audium/Koch, That's Why I Sing This Way, was mostly a cover album save for the title track. Both "That's Why I Sing This Way" and a cover of Conway Twitty's "I'd Love to Lay You Down" were released from this album, respectively reaching No. 47 and No. 43.
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", both failed to chart.
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.