Favorite Songs by Favorite Artists: Patty Loveless

This post was written by Blake Boldt. 

Patty Loveless has built a Hall of Fame-worthy career, one that has perfectly blended country music’s past and present into a trademark musical style that she can truly call her own, all the while selling gold and platinum and succeeding at country radio. Her mix of commercial and critical success is almost unsurpassed in modern-day country music.

Along with Tony Brown, and later with her producer husband Emory Gordy Jr., Loveless made a true effort to sing songs that were significant to her, wringing every last drop of emotion into each lyric. The listener felt every hopeful or hurtful moment, and I have selected my 25 favorites in a career filled with classics.

The emphasis is on her Epic recordings, although she had plenty of fine moments during her MCA days.



“Hurt Me Bad (in a Real Good Way)”

Up Against My Heart


One of Patty’s earlier successes, she sees the positive in a bad breakup. The light at the end of the tunnel was a new love, one she would have never found without going through the hard times.




Honky Tonk Angel


Loveless gives as good as she takes on this gem, her second #1 record. Is it rocket science? No. But Patty’s rarin’ to go from the first note. It is pure and simple fun as she portrays a woman  ready for romance but trying like mad to resist her man’s advances. She almost revels in the back-and-forth that comes with so many love affairs. This same spirit is captured in her future single “I’m That Kind of Girl.”



“To Have You Back Again”

Long Stretch of Lonesome


Loveless is among the walking wounded on this song, asking for forgiveness from the one she has done wrong. She strikes a beautiful balance between desperation and determination, sounding wise and yet aware of her weaknesses. She absolutely wails in the chorus, lending an immediacy to every little line.



“You Can Feel Bad”

The Trouble with the Truth


A bittersweet kiss-off to an old companion, this Matraca Berg tune was one of Patty”s five #1 singles, and it features a contemporary twist on the ol’ heartache song. Once she reaches the chorus, Loveless’ voice is a mix of resignation and indignation. She’s committed to overcoming the pain with a tough-to-the-core attitude that is not always apparent, but is always underneath the surface of much of her material.



“On Down the Line”

On Down the Line


The working woman’s anthem. As she says, she will keep on “Laughin’ and cryin’, livin’ and dyin’, on down the line”. The title cut of her 1990 collection, it is a message of a woman’s day-to-day drive to succeed (or even just survive).



“Soul of Constant Sorrow”

Mountain Soul


Although the O Brother version is much more renowned, Loveless instills a lonesome tone into this admission of the heart’s trials and troubles Her version is exquisite in its simple, sad beauty.



“Lonely Too Long”

The Trouble with the Truth


A one-night stand never sounded so good. Patty implores her lover not to regret, not to forget, but to appreciate the comfort and the company of one night together. Her voice throughout is matter-of-fact and just plain terrific. Performed live at the 1996 CMAs when she won her long-deserved Female Vocalist of the Year award, this was the last of Patty’s #1 singles, and possibly her best.



“A Little Bit in Love”

If My Heart Had Windows


So many of Loveless’ best moments are ballads, but she so clearly enjoys the feeling of new love that it is inescapable here. Tony Brown’s production tempts Loveless into one of the most audacious, engaging performances of her early career. This Steve Earle single was Patty’s breakout record, reaching #2 in 1988 and helping her to a first CMA Horizon Award nomination.



“Someday I Will Lead the Parade”

The Trouble with the Truth


Oftentimes, Loveless closes albums on a spiritual note. She delivers a command performance, daring to look back to the past and hope for the future. Imagining a time when “old friends gather near” and the mistakes of the past are forgiven, she awaits her journey to Heaven’s gate.



“Nothin’ but the Wheel”

Only What I Feel


An underrated, yet beautiful ballad about a woman, the road and the weight of dreams shattered. Her loneliness, just like Highway 41, is a long and winding path. Her lover has lost his affection for her, and she has lost all direction as she holds on to nothing but the steering wheel and her own steely resolve.



“Don’t Toss Us Away”

Honky Tonk Angel


Rodney Crowell lends his harmony vocals to this old-fashioned plea of love and devotion, and Patty puts her tough, yet tender voice into each word, praying her lover will once again commit to the love that is too good to lose.



“Sounds of Loneliness”

Mountain Soul


This plaintive ballad, a favorite of her father‘s, was Patty’s first true introduction to country music, the song that she sang for Porter Wagoner that convinced him to add her as the “girl singer” in his show. Made all by the more remarkable by the fact that Patty wrote it herself, “Sounds” is a deeply, dark exploration of a lonely soul. Found on her strongest artistic triumph, Mountain Soul, and also heard on her self-titled debut album, this song connects Patty with her past with considerable emotion.



“Lovin’ All Night”

On Your Way Home


Patty infuses this feisty rocker with just the right amount of sass and spunk. This rollicking number, her return to mainstream country after Mountain Soul and a cover of the 1992 Rodney Crowell single, exhibits no restraint. No doubt about it, “Lovin’” burns with great passion and pleasure.



“When the Fallen Angels Fly”

When Fallen Angels Fly


The title track to her 1995 CMA Album of the Year winner, Loveless acknowledges the sins and struggles that have marked her past, and pushes forward, rejoicing in the new love she has found and praising God’s guidance in this particular moment in time.



“You Don’t Even Know Who I Am”

When Fallen Angels Fly


The sad story of neglected love, this Gretchen Peters-penned tune shows the battle of the sexes is a two-sided fight. From both the male and female perspective, the song is a clear-cut portrayal of how two hearts can become so distanced. Loveless gives a wonderfully delicate reading.



“The Trouble with the Truth”

The Trouble with the Truth


Harlan Howard had to be proud of this masterfully written work – thank you, Gary Nicholson – that spells out the power of the truth in all its glory. Loveless’ voice is full and her heart is fragile as every note rings out in a testimony to honesty.



“Keep Your Distance”

Dreamin’ My Dreams


“With us it must be all or nothing at all”. As Loveless would say herself, this sentiment is deeply felt in many relationships. She tackles this tune, written by Richard Thompson and first popularized by Buddy & Julie Miller, with fierce determination. The sliding steel guitar intro and Loveless’ mountain wail made this the perfect introduction to 2005’s terrific Dreamin’ My Dreams.



“The Grandpa That I Know”

On Your Way Home


Easily one of country music’s best-ever ballads about death, Loveless takes on the character of a young girl experiencing her first funeral. As in most great country songs, this one is more about how you actually feel rather than how you should. And with every detail, she delivers a poignant piece that shows death as a possible beginning rather than an ending.



“You’ll Never Leave Harlan Alive”

Mountain Soul


Hauntingly similar to the life Loveless led in Pikeville, Kentucky, this story of the coal-mining town of Harlan is rich with honest-to-goodness resignation. There’s no hope to be found in the “deep, dark hills of Kentucky” as she examines the lives of those who have no choice to return to the mines merely to survive. Loveless gives a bone-chilling account with every note. As she says, “I always hope my music will be an open history book to anyone who listens.” With this song, she succeeds.



“Blame it on Your Heart”

Only What I Feel


This track is a personal testament to Patty’s perseverance, her first single release after potentially career-ending throat surgery in 1992. All the more sweet that this became the biggest radio success of her career. Admonishing a former flame for all his transgressions while seemingly enjoying the man‘s attention, Loveless rides the rhythms of this tongue-twister to great effect. Countless listeners of this 1993 #1 smash surely tried to sing along with a song about a man and his “lyin’, cheatin’, cold, dead-beatin’, two-timin’, double-dealin’, lovin’ heart”. Although, by the end, Loveless sounds a little more interested in the lovin’ than anything else.



“A Thousand Times a Day”

The Trouble With the Truth


Originally recorded by George Jones, the portrait painted in this song is not too far removed from the one of Loveless’ own life during an all too unforgiving past. She can swear off every bad habit, from the cigarettes to the alcohol, but not the despair of losing that special someone. But she’ll be damned if she does not keep trying to fight the memory, singing “Forgetting you, is not that hard to do. I’ve done it a thousand times a day”.



“You Don’t Seem to Miss Me” (with George Jones)

Long Stretch of Lonesome


Buoyed by the guest appearance of George Jones, this mid-tempo revelation is full of undeniable energy. The lyric describes a love that seems to be dying, and Loveless begs and pleads for her dear life with both strength and vulnerability. Patty proclaimed that George’s distinctive touch was the key element and refused to allow country radio to strip George‘s voice from the song to boost airplay. Loveless stuck to her guns, and the Country Music Association rewarded the pairing with the Vocal Event of the Year prize in 1998.



“On Your Way Home”

On Your Way Home


One of country radio’s worst crimes was ignoring this beautiful ballad. Matraca Berg and Ronnie Samoset show the conflicting emotions that come with being on the wrong side of cheating. The suspicious wife in this story wonders “Where do you go, on your way home?”, all the while faced with some difficult decisions. Will she stay just to spite him? Will she leave “like a bat outta Nashville”? Or will she just drown her husband in guilt one hard question at a time? A truly evocative piece of great country heartache. Killer steel guitar and honest-to-goodness country instruments, too.



“Here I Am”

When Fallen Angels Fly


Between the bourbon and the bitter heartache, Loveless plays a damaged woman who still carries around the curse of unrequited love. With every drink he drinks, with every woman he sees, with every memory he finds, she says “here I am”, until she’s gone from mocking him to admitting her love for him has never died.



“How Can I Help You Say Goodbye”

Only What I Feel


Her masterpiece. If not for a letter written by co-writer Burton Baker Collins, Loveless may have never recorded this song at all. His encouragement finally convinced her to record this gorgeous ballad about the winds of change. All the great losses of life, the death of a parent, the death of a marriage and the sadness of goodbye all in just five emotional minutes. As Loveless says, it was “the first song I can truly say I’ve experienced all the way. I’ve had to say goodbye so much. I know those feelings.” That connection with the lyric clearly resounded with fans and industry insiders.

It was released as the last single of her first album with Epic Records, and peaked at #3, a truly remarkable achievement for a long ballad. The Academy of Country Music, the Country Music Association and the Grammy committee rightly recognized the song, nominating it for Song of the Year, and Patty’s career reached new heights, resulting in future Female Vocalist of the Year wins from the ACMs and CMAs and the coveted Album of the Year trophy from the CMAs for her follow-up album When Fallen Angels Fly in 1995.


  1. An amazing list for an amazing artist. I know the song is silly but I’m surprised that I Try To Think About Elvis didn’t make the list.

  2. Great list, Blake. Welcome to the site. Patty is my favorite singer and I’m so excited about all the new music she has out this year. It’s hard to argue with any of your selections as I love all those songs. Here I Am is #1 for me. Some of my other favorites are songs that were never singles like Grandpa which you included.

  3. What an awesome list! The song choices are much like mine would be. The only two that I might have included were “Timber I’m Falling In Love” and “Mr. Man On The Moon.”

    Patty has one of the most achingly beautiful voices in country music. It’s certainly not genaric in any way.

  4. I like all the songs on your list although I would have found a way to work her recordings of “If My Heart Had Windows” and “Timber, I’m Falling In Love” onto the list

  5. Bless your heart for this one! I don’t know how I would begin to whittle down my Patty Loveless list.

    I LOVE “Here I Am”. To me, that song is so incredibly country and so “Nashville” (in a good way, not the Music Row way).
    Personally, I always thought “You Don’t Seem to Miss Me” would have been better sans George Jones. She is doing just fine on her own with the song and I always found his lazy vocals rather distracting and out of synch … as if a real after thought. Just my opinion, tho.

    She blows me away how she can switch from the upbeat tunes to the true ballads and make each song so unique… so “real” and believable.
    Patty Loveless has just never come across to me as an artist with an agenda. I find that in too many artists these days… ones I have been a fan of but then they introduce an agenda, being it going too commercial or introducing politics.
    Patty being Patty… THAT is why she still garners so much respect and is no doubt Hall of Fame-worthy.

  6. Thank you for the positive responses so far!

    Roger, your approval means a lot as I know how much of a fan you are from all the great comments you have left when Patty is mentioned.

    Leeann and Paul, I was torn with all four songs you mentioned, especially “Timber”. I felt “Timber” was right on the edge, and on another day, I may have included it. I love “Windows” as well.

    I would love for everyone to give their input, and even show your own Top 5 lists!

  7. Like Roger, my #1 would’ve been “Here I Am”, but I’ll settle for #2!
    I dig all of the songs on the list, though I’m in the minority among Loveless fans, as Mountain Soul isn’t one of my favorites by her.

    Some songs that you didn’t include that I love:

    “The Last Thing On My Mind”, “My Heart Will Never Break This Way Again”, and “Thirsty” from Strong Heart, one of my favorite albums of hers.

    “Timber I’m Falling in Love” – I never tire of it, especially with Vince’s awesome harmony part!

    “When Being Who You Are is Not Enough”, “On the Verge of Tears” and “Nobody Here By That Name” from Dreamin’ My Dreams.

    “A Handful of Dust” and “Ships” from When Fallen Angels Fly, my favorite Patty album.

    “Too Many Memories” from Long Stretch of Lonesome, which has my favorite line from a Loveless song: “What makes you grow old is replacing hope with regret.”

  8. Kevin, that quote from Too Many Memories is what I use as my “favorite quote” on various sites!

    I also am a huge fan of “On the Verge of Tears” and “My Heart Will Never Break This Way Again.” I’m totally biased though because there have only been a few cuts out of hundreds that I didn’t absolutely love.

    Blake, my top 5 is constantly changing. At the moment it is:
    1) Here I Am
    2) The Grandpa That I Know
    3) When the Fallen Angels Fly
    4) On Your Way Home
    5) On the Verge of Tears

    I love a great pop song I can sing in my car, but for some reason my true favorites are always the songs about breakups or death or some bad real-life situation.

    I am very happy to read so many comments from posters who I enjoy so much agree that Patty is Hall of Fame worthy. She has not had commercial success in a while and commercially never reached the heights of many of her contemporaries, but her music is so powerful that it is timeless.

  9. The first song I ever heard by Patty Loveless was “After All,” and although her career was just beginning, the performance told me she was going to continue to grow. So that song has always been a favorite of mine. Sure, Patty Loveless is Hall-of-Fame worthy, but really, the chances are slim for any woman to be inducted. The Country Music Hall of Fame is as bogus as the Rock and Roll Hall of Fame.

  10. I honestly could not find one song of Loveless’ that I dislike.

    Patty was able to sell her share of gold and platinum, and for a time in the mid-1990s, she was THE female singer as evidenced by her numerous awards during that time. She owns 20 Top Ten singles (compared 22 for Faith, 20 for Trisha, 19 for Martina), and her classic hits are a still a staple on many country radio stations. Hall of Famer, indeed. The YouTube clips of her award wins are wonderful to watch. They would definitely be included if we had a Best Awards Show Moments countdown….what do ya think, Kevin?

  11. “Blame it on Your Heart” was the first Loveless song I saw a video for, and while it helped get me hooked on her, I can rarely listen to it now. My favorites, from hands down one of my favorite Country artists:

    8) “The Boys are Back in Town”
    7) “That’s the Kinda Mood I’m In”
    6) “You’re So Cool” (Strong Heart)
    5) “Can’t Get Enough”
    4) “You Don’t Even Know Who I Am”
    3) “How Can I Help You Say Goodbye”
    2) “You Don’t Seem to Miss Me”
    1) “Lonely Too Long”

  12. Kevin,

    I can’t believe you mentioned Vince’s harmony before I did!:) You describe it just right.

    “I felt “Timber” was right on the edge, and on another day, I may have
    included it.”

    Blake, That’s often how I feel after one of these lists.

  13. Oh yeah Kevin,
    I’m a little sad that you don’t love Mountain Soul too much.

    I suppose I can give you Mountain Soul if you can give me Alan Jackson’s Like Red On A Rose.:)

  14. Patty was on “Opry Live” in the past couple of weeks and got to do 2-3 songs. She still sounds so wonderful, so country and genuine. The crowd totally appreciates her. She reminds me of what made the “girl singers” of the past wonderful and possessing the “staying power” they have.
    You know, she may not hit the charts and and be played into submission on the radio, BUT she’s country and she knows and appreciates what real country is.
    Plus, when she sings and interprets a song… she’s believable.

  15. GREAT topic Blake, great comments everyone. It is always very gratifying to see Patty get the recognition she deserves that is all too often denied her by the commercial Nashville establishment lately..”Country” radio and TV have become something less as of late, otherwise this supremely talented woman would continue at the top of the charts.

    Patty is worthy of the Hall of Fame, and I believe time will vindicate her greatness. We Patty fanatics can take comfort that she was so quickly inducted into the Opry, and that Patty has proven time and time again that Porter Wagoner’s faith in her was very well placed indeed. Also, she and Emory have a very well deserved spot in the Georgia music hall of fame, along with other timeless greats such as Ray Charles.

    I also know of no other Country singer who combines as much artistic greatness with a such a warm, fun and entertaining personality and musical persona as Patty. Her natural Country charisma is genuine, compelling and beyond compare.

    I guess my top five favorite Patty songs would be:

    5.That Kind of Girl
    4.Sorrowful Angels
    3.Big Chance
    2.The Grandpa that I Know and
    1.Keep Your Distance

    Thank you Blake and everyone for an amazing thread. You all made my day!

    -Steve from Boston

  16. Here’s my list:

    “Lovin’ All Night”
    “You Don’t Even Know Who I Am”
    “On Your Way Home”
    “You’ll Never Leave Harlan Alive”
    “Blame It On Your Heart”
    “How Can I Help You Say Goodbye”
    “The Grandpa That I Know”
    “Mr. Man On the Moon”
    “Don’t Toss Us Away”
    “Timber I’m Falling In Love”

  17. Great list Blake, my top five looks much like yours except for one. Remove “You Don’t Seem To Miss Me” and replace it with “Keep You Distance”, and put “On Your Way Home” at number one and it’s perfect.

  18. I’d just like to add that Patty Loveless, in continuing to make the kind of music she loves and believes in, makes the kind of music we love and believe in. She does this without regard to commercial currents, and proves that she will choose the timeless over the trendy every time. That is artistic integrity.

    If I had to choose between Patty Loveless, and everything that Nashville is offering today, I would choose Patty in a heartbeat, without blinking, without regret and without ever looking back.

    -Steve from Boston

  19. I would take another listen to Patty’s pre-1993 albums and revise this list. Her older stuff is just as good as her mid-90’s classics.

    Also, there ought to be room for “My Kind of Woman / My Kind of Man” with Vince Gill and, especially, “Send a Message to My Heart” with Dwight Yoakum. Both songs are easily among the 20 best in the Patty canon.

  20. Marcus Hummon is one of Nashville’s best songwriters. Some of his stuff’s on eMusic too. (The Sound of One Fan Clapping) and (“Looking For The Child”), which he released digitally online in 1999! Talk about ahead of the curve.

  21. Thanks for giving Patty prime time treatment! Here is my list

    1. Here I Am
    2. You’ll Never Leave Harlan Alive
    3. On Your Way Home
    4. Nothin’ But The Wheel
    5. A Thousand Times a Day
    6. How Can I Help You Say Goodbye
    7. If My Heart Had Windows
    8. Sounds Of Loneliness (Moutain Soul Version)
    9. Over My Shoulder
    10. Don’t Toss Us Away
    11. Trouble With The Truth
    12. Long Stretch of Lonesome
    13. My Kind of Woman/My Kind of Man
    14. I’m That Kind Of Girl
    15. Strong Heart
    16. Grandpa
    17. Old Weakness Coming on Strong
    18. Ships
    19. Can’t Stop Myself From Loving You
    20. Lonely Too Long
    21. Someday I will Lead The Parade
    22. My Heart will Never Break This Way Again
    23. You Don’t Know How Lucky You Are
    24. Where I’m Bound
    25. Looking In The Eyes Of Love

    Keep up the great work!

  22. I’ve always loved “Hurt Me Bad” and I’m glad to see it on here. Also: “To Have You Back Again,” and “Here I Am.”

    I’d also include:
    “Can’t Get Enough”
    “That’s the Kind of Mood I’m In”
    “The Last Thing On My Mind”
    “High On Love”
    “She Drew A Broken Heart”
    “Blue Memories”
    “The Night’s Too Long”
    the entire “Only What I Feel” album
    ditto for “Honky Tonk Angel.”

    My only problem with Patty Loveless is that when she had a big hit, it was a really BIG hit song that radio refused to stop playing. For that reason, right or wrong, whether it’s a genuinely good song or not, because I’m just so tired of hearing them, I change the station now whenever I hear:
    “How Can I Help You Say Goodbye”
    “I Try To Think About Elvis”
    “Blame It On Your Heart”
    “You Don’t Even Know Who I Am.”

  23. Kevin,

    It’s funny you say that. Because I was inspired by this feature so much, as I type, I’m going through her CDs and ripping the stuff that wasn’t already on my computer onto it right now.

  24. I am a great admirer of Patty’s, and have been on the bandwagon since that first CD nearly 20 years ago(!).

    My favorite song of hers is probably “Ships”, which appears on “When Fallen Angels Fly”. To me, this Gretchen Peters song expresses, better than anything, the possibility of second chances in love and life. It’s a three-minute movie, and Patty’s vocal is mature, sensitive and really heartfelt.

    Patty Loveless – the country singer for grown-ups…

    Dean Eaton, Cambridge MA

  25. My absolute favorites would have to be “Nothin’ But the Wheel” and “You’ll Never Leave Harlan Alive” and I usually tend to prefer her ballads (“Ship” also) but have enjoyed some of the more uptempo numbers as well (“That’s the Kind of Mood I’m In”, “High On Love”). One I could never quite catch on to though was “I Try To Think About Elvis”. It just seemed like a novelty and she is better than that. Thanks for a great read!

  26. I took Patty for granted throughout the 90s. She was constantly played on the radio it seemed, and was one of those artists you couldnt listen for more than an hour without hearing her. But now that those days are long gone, i can go back and realize how good i really had it.
    I have been listening to “Over My Shoulder” ALOT lately. Actually all of Patty’s songs have been on shuffle lately.

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