Daryle Singletary was born March 10, 1971 in Cairo, Georgia. His father, Roger Singletary, was a postal worker, while his mother, Anita, 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. In 1990, he moved to Nashville, Tennessee in pursuit of a record deal.
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.
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.
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.
In 2018, Platinum Records Nashville released a posthumous single titled "She's Been Cheatin' on Us". Although the label announced that the song's proceeds were to benefit his family, a representative of the singer stated that no such fund existed, and that the recording was a demo that was never meant to be released.
