Patty Loveless, with a lilting voice and a well of emotion, has released 16 solo studio albums (and several compilations) since her career began with her 1986 self-titled debut. In the late ’80s, she was, in many regards, part of the neb-traditionalist era in country music, a time which witnessed a return to more roots and traditional music in mainstream culture. It wasn’t until her sophomore LP, 1988’s If My Heart Had Windows, that she had her commercial breakthrough with a cover of the George Jones’ standard “If My Heart Had Windows.” The follow-up Honky Tonk Angel came later that year (a few months after she became an Opry member); the album spawned several massive hits, including “Timber, I’m Falling in Love” and “Chains.” Those classics were the catalysts that jumpstarted her prolific career, leading to On Down the Line in 1990, 1993’s Only What I Feel, 1994’s When Fallen Angels Fly and 1996’s near-perfect The Trouble with the Truth.
Of course, she’s released numerous other records since then, even after she moved away from mainstream and terrestrial airplay in favor of more bluegrass-leaning work.
In the middle of all this, I was born in 1986. As a kid, I can recall CMT being a centerpiece of my house. In fact, Patty’s Charlie Chaplin-esque “Chains” video was one of my earliest memories. It was when I was about 5-years-old that I was formally introduced to the songbird (who truly has changed the landscape for women) with her first greatest hits collection. From then, I began to dig into her catalog, through old records and cassette bins at Walmart. Because I had a family who loved and cherished country music, I was then able to really appreciate the finest musical genre on the planet. Needless to say, Patty’s catalog has been a rather influential vehicle on my life. If it wasn’t for her ethereal voice pouring out her heart on record, I (most likely) wouldn’t even be listening to or writing about country music today.
Here are the 10 definitive songs that changed my understanding of a genre deeply rooted in the American Heartland:
“If My Heart Had Windows” (from 1988’s If My Heart Had Windows)
Yes, this is a cover of George Jones, but Patty’s voice is powerful and full of pain. It was her first Top 10 hit on Billboard, and rightfully so. It was one of the first country songs I had ever heard; at the time, I had no idea it was a cover. Patty could rip your heart right out of your chest, no matter if the song was her own or not.
“Don’t Toss Us Away” (from 1988’s Honky Tonk Angel)
Again, another cover: this time she takes on Lone Justice’s 1985 original. There is just something innately delicate and commanding about she approaches a lyric. She meticulously choses interesting vocal choices to make a song wholly her own and drive home an earth-shattering message.
“Timber, I’m Falling in Love” (from 1988’s Honky Tonk Angel)
Early on, she proved she could singer about more than just pain. With this uptempo number, she examined her own romantic entanglements and how she become overwhelmingly enamored with a new romantic link.
“How Can I Help You Say Goodbye” (from 1993’s Only What I Feel)
Talk about a sucker punch to the gut. I was only 7, but even then, I knew the sheer devastation of “goodbye” and what it meant on my own home life. Timeless is an apt descriptor here.
“I Try to Think About Elvis” (from 1994’s When Fallen Angels Fly)
Following a breakup, she finds it incredibly difficult to focus on the tasks at hand, like her daily routine and shooting a music video. It’s cutting wit is precise, running down a long list of the things she’d much rather be thinking about. Sure, she’s a jilted lover, but it’s not watered down, only heightened by her confidence and strong will.
“Chains” (from 1988’s Honky Tonk Angel)
As I mentioned, this is one of the very first music videos I ever remember. I was absolutely mesmerized by the interplay of black and white footage, vaudeville humor and Patty’s cheeky wink-wink to the camera.
“Blame It on Your Heart” (from 1993’s Only What I Feel)
Patty’s rock-soaked entry into female empowerment anthems came at the beginning of the female resurgence in Nashville. She stamped radio with this charming, compelling and downright satisfying track
“You Don’t Even Know Who I Am” (from 1994’s When Fallen Angels Fly)
As far as her moving ballads go, this is one of her finest. It’s nearly acoustic arrangement is also an exceedingly impressive landscape melding distinct bluegrass and folk influence. It’s a story song at its core about separation and finding the strength to leave in order to achieve freedom.
“I’m That Kind of Girl” (from 1990’s On Down the Line)
Patty was always one to use a bit of humor to get her point across. As she attempts to woo her Romeo, she lets him know point-blank that she’s looking for more than a one-night stand. She’s not the “woman in red” or “the girl next door,” but if you’re looking for somewhere in the middle, she’s “that kind of girl.”
“Hurt Me Bad (In a Real Good Way)” (from 1991’s Up Against My Heart)
Simply put: this is one of the finest recordings in country music history.
Bonus Favorites: “Tear-Stained Letter” (1996’s The Trouble with the Truth), “You Can Feel Bad” (1996’s The Trouble with the Truth), “Lonely Too Long” (1996’s The Trouble with the Truth), “Jealous Bone” (1991’s Up Against My Heart)