Whether it’s classic ‘80s and ‘90s country or rootsy Bluegrass music, Patty Loveless’s discography has it all.
With several awards to her name, including Grammy, CMA and ACM honors, Loveless’ country icon status is undeniable. Frequently drawing from her Kentucky roots and passion for authentic storytelling, Loveless’ catalog offers something for everyone.
To celebrate her recent 2023 Country Music Hall of Fame induction, Holler’s looking back at the Top 15 songs in Loveless’ career.
Forlorn lyrics run like a through line on some of Loveless’ most notable songs, as evidenced in this mid-tempo tune.
Released in 1989 as finds Loveless drowning in misery, as she ruminates on her dissolved relationship and adjusting to a new life of singlehood.
One thing’s clear in this song: Loveless is done feeling crushed by her old flame.
Boasting a more commercial sound, the singer simply tells the ex with unrestrained feist, “You can feel bad if it makes you feel better.”
Since she’s not drowning in post-breakup misery, it has listeners wondering: Was Loveless staying in the relationship longer than she should have?
While Loveless didn’t write this imager-rich Bluegrass tune, the Kentucky native does an impeccable job at pulling from her roots to paint a musical remembrance of the sometimes insufferable state of Kentucky coal miners.
The most poignant line of the song?
“You spend your life diggin' coal from the bottom of your grave.”
Heartache cascades like an endless river in this mid-tempo ballad.
Preceding 'Timber I’m Falling In Love' as a single, 'Don’t Toss Us Away' finds Loveless pleading with her lover to think twice before calling it quits on their relationship.
“I still love you, I want you to stay / Darling please, don't toss us away,” she implores.
“I don't fall in love as a rule / Cause it always made me look like a fool,” Loveless declares right from the start of the song.
But what happens next doesn’t quite match that statement as she makes up all kinds of excuses for “letting my guard down” and falling in love, once again.
Well, haven’t we all been there before?
This is undeniably one of the standout tracks on Loveless’ 2001 album, Mountain Soul.
Penned by the elder statesman of Bluegrass music Ralph Stanley, the rootsy and bible-referencing 'Daniel Prayed' features Loveless’ spirited vocal delivery alongside assistance from fellow Kentucky native and Grand Ole Opry member, Ricky Skaggs.
Talk about an organic pairing that fits perfectly.
Heartache has nothing on Loveless in this uptempo number.
Serving as the lead single from 1988’s Honky Tonk Angel, Loveless embraces her post-breakup in true country fashion in the 'Blue Side of Town.'
“Well, there's a honky tonk where the lights are low and they play the saddest songs / Dark shadows fall like broken dreams on the lost and lonely ones,” she sings with pride and joy for her new safe haven.
“I'm gettin' tired of these one-night stands / But if you wanna make a real romance / I'm that kind of girl,” Loveless declares.
As we grow older, our outlook on fleeting romance changes and the yearning for a long-lasting one starts taking root.
This song spotlights that sentiment and Loveless’ desire to settle down with someone who’ll love her for who she really is.
The story in this song has the ability to both ache and heal a broken heart.
Here, Loveless grapples with the different degrees of loss in her life, which includes leaving her hometown, going through a divorce and spending her mom’s final living moments with her.
Some of the best country songs are about real-life pain and hurt, and 'How Can I Help You Say Goodbye' captures that to a T.
Whether you relate to this heartbreak narrative or not, Loveless will have you singing, “chains, chains, shackles and chains,” with her in no time.
On this No. 1 single, Loveless equates an old romance to the unbreakable bond between metal chains.
The ship’s sailed and the relationship has sunsetted, but still, emotions linger as Loveless vows to “break these chains.”
If Loveless had a 'Boot Scootin’ Boogie'-equivalent track, this just might be the top contender.
The exuberant 'I Try To Think About Elvis' finds Loveless incredibly frustrated that her old flame is “all [she] thinks about these days,” despite thinking about Elvis, The Beatles, The Rolling Stones, sushi, tattoos and more.
He’s occupying every corner of her mind and she evidently needs more than the King of Rock ‘n’ Roll to forget him.
Penned by hit songwriter Jim Lauderdale, this searing ballad features melancholy lyrics and Loveless’ tear-soaked delivery as she questions why her relationship isn’t working out.
“I'm going back / I wonder why I'm runnin' fast to get home / I just can't wait to see your face but you don't seem to miss me,” sings Loveless as the incomparable George Jones harmonizes and provides backing vocals.
This duet earned the pair a CMA Musical Event of the Year award in 1998.
Unfortunately, not every married couple gets to enjoy a happily ever after — a sentiment Loveless captures flawlessly in her 1996 chart-topper.
Composed by Gretchen Peters, the vulnerable, slow-burning ballad chronicles a marriage that’s torn asunder as both husband and wife fail to reconcile differences and begin to grow apart.
Artists never forget their first No. 1 single, and neither do fans. This beloved Loveless favorite is one of those quintessential ‘80s country classics.
The jubilant singalong captures the vibrance of summer love and young, head-over-heels romance.
“It started slow, it's coming fast / I got a feelin’ it's gonna last / Timber I'm falling in love,” Loveless sings with unrestrained passion in the chorus.
Another generation-transcending country classic, 'Blame It On Your Heart' is, alongside 'Timber I’m Falling In Love,' Loveless’ most recognized hits.
The catchy upbeat offering melds sass, angst and revenge into a memorably wicked bonafide country track.
“Blame it on your lying, cheating, cold, dead-beatin’, two-timing, double-dealing, mean, mistreatin’, lovin' heart,” Loveless sings in the kiss-off chorus after gloating over her ex’s well-deserved misfortunes.
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