Raised in eastern Kentucky, Patty Loveless was born with the high lonesome sound that only folks from the Bluegrass State seem to have. A distant cousin of Loretta Lynn (and the daughter of a coal miner herself), Loveless knew country music was in her soul from a young age.
After a brief run in Nashville, where she was mentored by Porter Wagoner and Dolly Parton, the newly married young singer left town and headed for North Carolina, where she spent her days waitressing and her nights singing bluesy rock covers in Charlotte, N.C. bars.
All those nights singing to the lost and heartbroken would serve her well when she finally did move back to Nashville. In 1985, Loveless released her first single “Lonely Days, Lonely Nights” and released her debut, self-titled album two years later. The next year, she joined the Grand Ole Opry and released her second album If My Heart Had Windows, featuring the George Jones cover of the same name.
It was her third album, Honky Tonk Angel, that earned Loveless the commercial success she deserved. The record spawned No. 1 singles “Chains” and “Timber, I’m Falling in Love,” along with the top 10 hit “The Lonely Side of Love.”
The ’90s saw her career skyrocket with the release of Only What I Feel, which spawned the No. 1 hit “Blame it on Your Heart,” along with fan favorites “Mr. Man on the Moon” and “You Burned the Bridges.” The masterful follow-up When Fallen Angels Fly was named Album of the Year by the CMA — only the second album by a female artist to win the title. In 1996, she released The Trouble With the Truth (“Tear-Stained Letter, “She Drew a Broken Heart”) and took home the CMA and ACM awards for Female Vocalist of the Year.
Her Kentucky holler-born voice lent itself to duets with peers and idols, such as Vince Gill (“My Kind of Woman, My Kind of Man”), George Strait (“House of Cash”) and George Jones (“You Don’t Seem to Miss Me”).
Though her late ’90s album Long Stretch of Lonesome and 2000 release Strong Heart (“The Last Thing On My Mind”) did well on the albums charts, country radio was headed in a more pop-friendly direction. Loveless returned to her Kentucky roots to record the bluegrass album Mountain Soul (“Daniel Prayed,” “The Richest Fool Alive).” A mix of originals (“Sorrowful Angels”) and bluegrass standards (“Soul of Constant Sorrow,” “Pretty Little Miss”), the album stands as one of Loveless’ best works. (Eight years later, the follow-up, Mountain Soul II, would win a Grammy for Best Bluegrass Album.) In 2002, she released Bluegrass & White Snow: A Mountain Christmas, featuring stunning renditions of “Little Drummer Boy,” “Silent Night” and “Silver Bells.”
She returned to country radio with her acclaimed 2003 album On Your Way Home, which merged her country and bluegrass roots with songs like “Cheap Whiskey” and “Last in a Long Lonesome Line.” Five years later, she released Sleepless Nights, which honored country classics she grew up on like “Crazy Arms” and “Please Help Me I’m Falling.”
From dive bar rockers (“Jealous Bone,” “Wicked Ways”) to stone-cold country weepers (“I’ve Got to Stop Loving You and Start Living Again), Patty Loveless was a leader in the traditionalist revival of the late ’80s an early ’90s. Her songs told stories about women starting over, falling in love and not backing down. Through it all, she crafted a career that inspired countless artists who followed in her footsteps, such as Miranda Lambert, Angaleena Presley and Sunny Sweeney.
From a country rocker to a honky tonk kiss-off, read our list of the 15 best Patty Loveless songs, ranked.
“Old Weakness (Comin’ On Strong)”
Written by Bob DiPiero and Gary Nicholson, this hard-driving, bluesy tune about a love that won’t let go proved that Loveless could rock as hard as she could deliver country gold.
“Nothin’ But the Wheel”
The second single from Loveless’ 1993 album Only What I Feel, “Nothin’ But the Wheel” is the ultimate leavin’ song. You can practically hear the trucks rushing by as Patty sings of a lonely night on the road to a new life, with only the headlights and little white lines to keep her company.
“Lonely Too Long”
This tune about navigating a new relationship after heartache is Loveless at her best. “Lonely Too Long” hit No. 1 on the Billboard country chart in 1996.
“I Try to Think About Elvis”
Written by Gary Burr, the infectious “I Try to Think About Elvis” may be the best country song to namedrop both Elvis and Oprah. The track was the first single from When Fallen Angels Fly and was a top 5 hit for Loveless.
“The Night’s Too Long”
Originally written and recorded by Lucinda Williams, “The Night’s Too Long” follows a small town girl desperate to make a new start. Even 30 years later, the song stands out for its frank depiction of female desire.
“A Thousand Times a Day”
If anyone can tackle a song originally recorded by George Jones, it’s Patty Loveless. The singer released the heartbreaker as the second single from her 1996 album The Trouble With the Truth.
Read More: 20 Best Country Albums by Female Artists
“You’ll Never Leave Harlan Alive”
Written by singer-songwriter Darrell Scott, “You’ll Never Leave Harlan Alive” captures the pain and struggle of coal miners and their families. It was something the Kentucky-born Loveless knew all too well. The singer included a spellbinding rendition of the song for her 2001 bluegrass album, Mountain Soul.
“I’m That Kind of Girl”
The third single from Loveless’ album On Down the Line, the sassy “I’m That Kind of Girl” is still an anthem for anyone navigating the murky waters of the dating scene.
“On Your Way Home”
Written by Matraca Berg and Ronnie Samoset, “On Your Way Home” is an interrogation of a cheating partner that’s equally heartbreaking and satisfying. “If you keep on lying’ to me, I might stay right here just to spite you” should go down as some of the best lyrics to ever appear in a done-me-wrong song. It’s a tear-in-your-beer track that’s yet another reminder that Loveless was born to sing country music.
“You Can Feel Bad”
Another track co-written by Matraca Berg (along with Tim Krekel), “You Can Feel Bad” finds Loveless dressing down a former flame who thinks she’s falling apart over the demise of their relationship.
“How Can I Help You Say Goodbye”
One of the most hard-hitting songs of loss of the ’90s, “How Can I Help You Say Goodbye” was a top 5 hit for Loveless in 1994. Much like Vince Gill’s “Go Rest High on That Mountain,” which Loveless lent vocals to, the song remains one of the most striking country songs about death and grieving.
“Hurt Me Bad (In a Real Good Way)”
This 1991 country shuffle about a heartbreak that opened a door to a new love was a top 5 hit for Loveless.
“Here I Am”
One of the most stunning songs from When Fallen Angels Fly, the Tony Arata-penned “Here I Am” positioned Loveless as a torchbearer for traditional country in the modern age. There may be no better country lyric than “Honey, I’m right there waitin’ on you at the bottom of your glass”
“You Don’t Even Know Who I Am”
Country artists haven’t shied away from singing about divorce. George and Tammy’s “Golden Ring” and (obviously) Tammy’s “D-I-V-O-R-C-E,” country explored the reality of what happens when a marriage falls apart. But the Gretchen Peters-penned “You Don’t Even Know Who I Am” goes one step further, spinning an elegy for a broken relationship that gives both husband and wife an equal chance to reflect on what made it all unravel.
“Blame it on Your Heart”
Written by Music City hitmakers Kostas and Harlan Howard, “Blame It On Your Heart” is the ultimate kiss-off to an unfaithful partner. It may seem like an obvious choice, but there’s a reason it’s her biggest hit to date. Loveless eviscerating her “lying, cheating, cold dead-beating, double-dealing, mean-mistreating” ex is as gratifying today as it was 25 years ago.