The 15 Best Songs by Patty Loveless

Emerging as part of the neo-traditionalist era of country music, Patty Loveless’ voice defined an entire generation of fans.

From her self-titled debut to 2009’s Mountain Soul II , the singer could carry you into her world of heart-torn balladry or the struggles of coal miners and their families. Her performances could always puncture the heart in ways her peers could not.

Born in eastern Kentucky, Loveless vaulted to commercial success with Honky Tonk Angel , which spawned such hits as “Chains” and “Timber I’m Falling in Love.” Throughout the 1990s, she became a household name for her perfect blend of tradition and a progressive-style country.

More hits followed throughout the next decade, including “Blame It on Your Heart,” as well as such accolades as Female Vocalist of the Year at the CMA Awards. Albums came fast and furious— The Trouble with the Truth and the CMA-winning When Fallen Angels Fly among her best.

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Eventually, country radio phased her out of the airwaves, so she eventually returned to her Kentucky roots for the bluegrass-centric Mountain Soul . Over the coming years, she released more acclaimed records, including 2003’s On Your Way Home and Sleepless Nights , the latter a covers collection honoring many of the greats.

Decades later, Patty Loveless stands as one of the greats herself. She might not have released an album in over a decade, but her work stands on its own. Her catalog testifies to how country music can still be modern and pay tribute to the past. There’s nothing else like her extensive work.

Below, we’ve compiled the singer’s 15 songs spanning her entire career. Have a seat and settle in; it’s a fun little ride.

“Blame It on Your Heart”

“You made a bad mistake, oh yeah,” sings Loveless. Rattling drums accompany a cheeky lead vocal, one that has had about enough of a lover’s “mean, mistreating, loving heart.” The singer slyly skates over the melody, cascading into an emotional explosion by the finale. If you’re target of her fevered emotions, you better run.

“How Can I Help You Say Goodbye”

Get ready for one of the all-time tearjerks. It’s an emotional gut punch that takes no prisoners. With a three-verse structure, “How Can I Help You Say Goodbye” finds Loveless pulling in the reins to allow the story to guide her hand. It’s not about an acrobatic vocal, but rather on that steeps in the sharp, brutal reality of life. It’s enough to push you on the floor.

“If My Heart Had Windows”

Give Loveless a ballad, and she’ll make you weep in seconds. “If My Heart Had Windows,” the titular cut to her third studio album, drips with teardrops over simple piano. Little else follows her vocal tracks, so you can feel every ounce of emotion in a way that you just don’t get in most other songs. “You’d see a heart full of love just for you,” she sings.

“Tear Stained Letter”

Drums pummel the eardrums from the very first frame, setting the raucous stage for a song with plenty of giddy-up. Loveless has just undergone a tremendous heartbreak, and just when she “thought things would get better, right through the door came a tear-stained letter,” she sings with pep. She attempts to shrug it off, but even she can’t escape the pain.

“You Don’t Even Know Who I Am”

With guitar in tow, Loveless carves out the listener’s heart as she tries to make sense of a marriage falling apart. “She left a note in the kitchen, next to the grocery list,” sings, before launching with a wail into the chorus. “You don’t even know who I am!” she cries into a flurry of production. “So why do you care if I go.” The pain hangs like acid on her tongue, and her performance is nearly as damaging.

“Don’t Toss Us Away”

“The love’s grown cold,” sings Loveless over a trembling guitar. Her voice mourns the burning out of a relationship. “I still love you,” she admits. “I want you to stay.” But her words fall without a sound. No one is listening, but she pushes her please through anyway. From the tenderness in her vocals to the lyrics’ merciless begging, “Don’t Toss Us Away” stands as quite a showpiece.

“A Thousand Times a Day”

Loveless can’t seem to get an ex off her mind, at least for a time. “One more bad habit gone,” she sings, letting go of various vices to alleviate the pain. “I’m alright, yeah, I’m okay,” she adds. “Forgetting you is not that hard to do…” “A Thousand Times a Day” finds the singer learning to forgive and forget the past, leaving her far stronger than before.

“I Try to Think About Elvis”

Who hasn’t thought about Elvis? One of her more playful on this list, “I Try to Think About Elvis” lists various things she uses as distractions to keep her from thinking about a new crush. “I just can’t concentrate,” she sings. “You’re all I think about these days.” With a bit of a giddy-up, Loveless’ essential entry is just plain fun.

“Dear Miss Loretta” with Carly Pearce

A collaboration with one of the genre’s best bright spots, Carly Pearce, “Dear Miss Loretta” sees both singers pay tribute to none other than coal miner’s daughter herself, Loretta Lynn. “I’m a long way from Kentucky but the hurting’s the same,” sings Pearce, with Loveless packing on the harmony. “I started out broken / What ended up lost, I started out hoping / A lifetime of pain was three minutes long,” Loveless unravels in her verse. The pain in both verses knocks you down. It’s that potent.

“Chains”

A 1980s gem, “Chains” is melodically lighthearted, masking some deep emotional wounds. “No matter what it takes, someday I’m gonna break these chains,” she sings. The push and pull of a tumultuous relationship inform her ebbing and flowing vocal, as pained as it is playful. “Love was never meant to be a one-way street,” she advises. But still, she comes back time and again. Maybe one day she’ll break those chains for good.

“You’ll Never Leave Harlan Alive”

Off her excellent Mountain Soul, Loveless sings about the struggle of coal miners and their families. Considering the singer is from Kentucky, it hits home in a very real, raw way. Loveless infusions her vocals with the stark, brutal reality of the lower working class. By the final line, you might be cleaning up a puddle of tears.

“Lonely Too Long”

Still stricken with heartache, Loveless turns to a new lover for comfort. “No, we ain’t done nothing wrong,” she sings. Even though the prospect of love is enticing, she knows that it’s far too soon for such a commitment. Instead, she embraces the moments of fleeting passion.

“Here I Am”

Loveless makes quite the declaration: “Honey, I’m right there waitin’ on you at the bottom of your glass.” She sings that she’s everywhere now, in the aftermath of heartache. Her memory stings and lingers wherever her ex goes. It’s a soul-ripping piece of music that grabs you and doesn’t let go.

“Nothin’ But the Wheel”

Patty Loveless packs up her car and heads out on the lonely highway, “trying to explain the way I feel,” she sings. The horizon stretches out ahead of her, and even though her heart is in tatters, she knows that ultimately leavin’ the past behind is the best and only option. The pain is too much to bear, and certainly time will heal her wounds.

“On Your Way Home”

“Did you have to make a deal or wrestle for control of the wheel from your conscience?” Loveless asks, tears welling up behind her eyes. “On Your Way Home” revs its engines with emotional propulsion. There’s no ignoring the way she carves out the heart, as she leaves it on the floor. There is such force in her performance that will haunt you.