Born March 10, 1971, Daryle Singletary kicked off his country music career after moving to Nashville in the early 1990s. He got his big break after Randy Travis listened to a demo tape recorded by Singletary. Travis decided to record the song himself years later, but was so impressed with Singletary's talents at the time that he recommended him to his own management team. That relationship eventually led to a record deal with Giant Records, who released Singletary's self-titled debut album in 1995. That record, which was co-produced by Travis, spawned two Top 5 hits on the country charts.
Singletary released two more albums before the year 2000, snagging another No. 2 hit along with a handful of other Top 40 singles. After signing a new label deal, the Georgia native found success with two cover songs - one modern pop hit and one beloved classic country tune. Although he never found the same success in country radio as he did during the 1990s, Singletary stayed active in the country music scene. He regularly collaborated with established country legends and fellow new artists from the time, including a full album with Rhonda Vincent in 2017. He performed at CMA Fest 2017's Forever Country stage, alongside fellow 90s country hitmakers Doug Supernaw, Lari White, Mark Wills and Darryl Worley.
On Feb. 12, 2018, Singletary died unexpectedly at his home in Lebanon, Tenn. from a blood clot. He was 46 years old.
Singletary was known for his deep, soulful voice that often echoed greats from country's past, from Keith Whitley to Conway Twitty. His bright, warm personality shined both on stage and off, earning him a long and dedicated fan base who supported him through a career spanning eight studio albums and twenty-three years.
Although Singletary's life and career were cut far too short, his legacy lives on through his impressive catalog of music. Here are 15 Daryle Singletary songs that showcase his incredible talents as a country singer-songwriter.
"I Let Her Lie"From: 'Daryle Singletary' (1995)
Written by Tim Johnson, "I Let Her Lie" became the biggest hit of Singletary's career. The song peaked at No. 2 on Billboard's Hot Country chart and positioned him as one of the most intriguing new country voices of the decade.
"Too Much Fun"From: 'Daryle Singletary' (1995)
Singletary released "Too Much Fun" to follow up the success of "I Let Her Lie" earlier in the year. The upbeat song, which made it to No. 4 on the country charts, encapuslated the rollicking, carefree feel that took hold of the genre during the early to mid 1990s.
"I'm Living Up to Her Low Expectations"From: 'Daryle Singletary' (1995)
Before "I Let Her Lie" catapulted him to the top of the charts, Singletary released his debut single "I'm Living Up to Her Low Expectations" in early 1995. Penned by Bob McDill and Tommy Rocco, the honky tonk tune is one of the more underrated tracks from his first album.
"Amen Kind of Love"From: 'All Because of You' (1996)
This sweet love song was the first single from Singletary's second album All Because of You. It peaked at No. 2 on the country charts, and became a fan favorite for its mesh of heartfelt lyrics and traditional country accompaniment.
"The Note"From: 'Ain't It the Truth' (1998)
Penned by Buck Moore and Michele Ray, "The Note" was Singletary's first single from his 1998 record Ain't It the Truth. The song was previously recorded by other country heavyweights, including Conway Twitty, Gene Watson and Tammy Wynette. Singletary's version was the most successful, peaking at No. 9 on the Billboard country charts.
"I Knew I Loved You"From: 'Now and Again' (2000)
One of the most surprising moments of Singletary's career came with the release of "I Knew I Loved You," a ballad that had just became a hit for pop duo Savage Garden months earlier. His version put an unexpected country spin on the song, managing a feat that few artists could successfully pull off.
"That's Why I Sing This Way"From: 'That's Why I Sing This Way' (2002)
The title track of Singletary's 2002 record is one of the best representations of his sound and artistic viewpoint. A story song with a sense of humor, the track worked well alongside the record's track listing, which included collaborations with Merle Haggard, George Jones and Dwight Yoakam.
"I'd Love to Lay You Down"From: 'That's Why I Sing This Way' (2002)
Singletary released his cover of Conway Twitty's iconic hit "I'd Love to Lay You Down" as a single from That's Why I Sing This Way. His rendition, which stayed true to the familiar original, showcased Singletary's ability to make a song his own while still keeping the sound rooted in traditional country.
"Take Me Home Country Roads"From: 'Rockin' in the Country' (2009)
It's never an easy task to try and bring a brand new sound to an already beloved classic. Singletary's version of John Denver's "Take Me Home Country Roads" adds a slow groove and steel guitar accompaniment that transforms it into a hit worthy of any honky tonk bar's jukebox.
"One" (with Rhonda Vincent)From: 'American Grandstand' (2017)
In 2017, Singletary teamed up with his longtime friend Rhonda Vincent to record American Grandstand, a duet album that featured a mix of new material and covers of country classics. Their take on this George Jones and Tammy Wynette collaboration showed off their individual talents while supplying an engaging blend of traditionalism and modernity.
"A Thing Called Love"From: 'Ain't It the Truth' (1998)
Over the years, Singletary recorded an array of cover songs from classic country's biggest names. His take on this Jerry Reed tune focuses on the humanity and grace weaved into the song's lyrics. Although it wasn't released as a single, it's still one of the most popular and highly streamed tracks from Ain't It the Truth.
"The Used to Be's"From: 'All Because of You' (1996)
This track, written by Michael Huffman, Donny Kees and Bob Morrison, was released as a single from his second studio album. Through his emotive vocals, Singletary tapped into the pain of regret after losing the one you love.
"Spilled Whiskey"From: 'There's Still a Little Country Left' (2015)
"Spilled Whiskey" is featured on Singletary's 2015 record There's Still a Little Country Left, which would become the final album of his career. He serves up another cleverly-writen story song, this time about a love akin to a fast-burning flame. Sonically, the track stays centered around his trademark traditional sound, creating a timeless sound with ease.
"Even the Wind"From: 'All Because of You' (1996)
Written by accomplished songwriter Hank Cochran and Tim Johnson, "Even the Wind" is a honky tonk tearjerker that finds Singletary trying to sort out his emotions after being left behind.
"Old Violin"From: 'That's Why I Sing This Way' (2002)
Singletary recorded his own version of Johnny Paycheck's "Old Violin" for his 2002 album That's Why I Sing This Way. His rendition was a fan favorite and was often included in his live sets. Two days before his death, Singletary closed what would be his final show in Lafayette, La. with a powerful performance of the song.