On to the next ten sad country songs…
Sad Country Songs Part 3
30) What Mattered Most – Ty Herndon
It isn’t often that a kid out of nowhere comes out with a song that hits home with so many country fans. In 1995, such a thing happened with newcomer Ty Herndon. The song was What Mattered Most and it shot straight to the top spot on the country charts in just a few weeks in 1995. The song is about a guy that lost his girl. The guy realized he knew all of the things on the surface, but never paid attention to what his woman actually wanted. He didn’t pay attention to her dreams and what she wanted for her life. As a result he lost her and the love they had. It’s a sad song and Herndon put an amazing vocal on the track and became an overnight sensation. Ty repeated the success a few more times. He was down and out for a few years, but is back touring and recording again. It all started with one sad song back on 1995.
29) I Can’t Do That Anymore – Faith Hill
Faith Hill was on a roll by the time she released the 5th single from her sophomore album. The song was an unlikely hit yet it reached the the top ten at the tail end of ’96. The song was I Can’t Do That Anymore. It was written by fellow country star Alan Jackson. The song tells the story of a woman sick and tired of letting her husband follow his dreams while she stays home and lives her life 100% for him. Woman need a little something of their own as the narrator in the song says. It’s a sad song that is a true story for many out there are supporting their loved ones in a way that takes away everything they have. Relationships seem to be best when each gets to follow their dreams.
28) Believe – Brooks & Dunn
In 2005, the greatest duo in country music history had one of their biggest hits. Even though Believe by Brooks & Dunn only reached #8 on the charts its gone on to become one of their fans’ favorites. The song tells the story of a young man that learns from a few stories an old man tells him over the summers. The song is religious and hopeful for life with loved ones after the one we live on Earth. It’s positive and yearning. There has to be more than just one trip around. All the hurt and pain…there has to be more. For B&D the song touched many that yearned for more and the song brings about tears in just about all fans’ eyes when it comes on over the radio speakers. Those are the powerful sad songs – the ones that share emotion that others feel.
27) Teardrops On My Guitar – Taylor Swift
Newcomer Taylor Swift had her second big hit on the American country charts in the middle of 2007 with the sad teenage country song Teardrops On My Guitar. The song was catchy as all hell and every heartbroken teen girl was singing the blues along with Taylor. The song is a story about a girl that falls for a guy that is with someone else. The narrator sees signs that maybe, just maybe he actually likes her a little more, but in the end her crush, Drew, just doesn’t share the same feelings. It’s heartache in the purest form and 16 year old Taylor was able to capture the emotion of a million other young girls were going through and the song catapulted Taylor Swift to superstardom.
26) Monday Morning Church – Alan Jackson
More loved lost hit home with Alan Jackson and his 2004 top five hit Monday Morning Church. The song is a story told by a narrator that has lost his wife to death. He is dealing with a wavering faith. He just can’t understand why the one he loved most in the world was taken from him. He’s left with only himself and the pain and emptiness he has. He says that his heart is now as empty as a Monday morning church. There is no better sad song country singer that Alan Jackson. AJ Was inspired by the soulful singing of George Jones and it shows on emotional tunes like Monday Morning Church.
25) Stupid Boy – Keith Urban
Country pop singer Keith Urban had an unlikely hit in early 2007 with the somber Stupid Boy. The song was co-written by fellow country singer Sarah Buxton. The song is written in the perspective of a woman that was scorned by her stupid boy. Urban knew the song was special and his wife Nicole Kidman convinced him that he could sing it as the stupid boy that screwed up. He took her advice and the song became a top three hit and one of today’s saddest country songs. There are a lot of stupid boys out there that take for granted the love they have from wonderful girls. Even if they realize it later on it’s usually too late for the guys to fix things. They simply need to learn from their own mistakes and hope for the best when love comes back around again.
24) I Miss My Friend – Darryl Worley
For his second album country singer Darryl Worley released the passionate, soulful song I Miss My Friend. The 2002 song raced right up the charts and became Darryl’s first #1 hit. The song is a sad tale of a guy that lost his lover and his best friend in the world. He misses his best friend that was his former lover. The song hit home with lots of folks that were feeling the same kind of loneliness. When it comes to breaking up with a girlfriend or boyfriend, husband or wife there is a lot of questioning that goes on in each others’ minds. Was it right to break up? Can you get back together. It’s enough to drive you crazy. The only thing that can heal the pain is time and to help pass the time there are songs like I Miss My Friend.
23) Can’t Be Really Gone – Tim McGraw
In the mid and late ’90s Tim McGraw had a run like no other. His songs all seemed to skyrocket to the top of the charts. One of those songs was the heartbroken sad ballad Can’t Be Really Gone. The song reached #2 at the tail end of 1995 and became one of his cult fan favorite hits. The song is about a guy that just can’t come to terms with the fact that his lover has left him. He keeps walking through the house and seeing all of her things. How could she just up and leave without taking all of the stuff she cared about so much? She can’t be really gone… It’s the denial part of loved lost and it’s an emotion felt by many that find themselves in breakups. It’s a great sad country song and one that truly belongs on this list.
Update: As one comment points out – the song could also be about losing someone to death. Also very sad.
22) When I Call Your Name – Vince Gill
Vince Gill had a breakout hit in 1990 with the powerful sad song When I Call Your Name. The song is classic country heartbreak. The song is a story about a guy that comes home and hears nothing when he calls the name of his lover. She’s left him after realizing she was living a lie by being with him. Sometimes one person in a relationship realizes that it’s just not going to work out and they have to leave and get on with their life. It’s too bad yet it’s probably for the best. The person that is left is taken aback like the narrator of this song and that leads to heartbreak. It makes for a great country song and one that people can relate to. The song made Vince Gill a star and he’s still going strong today.
21) Miss Emily’s Picture – John Conlee
In 1981, classic country singer John Conlee came out with the #2 hit Miss Emily’s Picture. The song is a sad tune about a guy that has lost a loved one. He struggles to get through each day without her. The poor guy keeps running into all the pictures of his Miss Emily throughout the day and it keeps bringing about the memories he had with her. It’s painful when you lose someone and there is just about no lonelier feeling that knowing you’re no longer going to be with someone you love. The song has a lonely melody and fits right in with someone going through love lost. Even though it’s sad the song serves as one of those songs that can heal through it’s storytelling. By knowing others go through the same thing Miss Emily’s Picture is a classic country therapy song.
The Saddest Country Songs of All Time
The Saddest Country Songs of All Time Part 2
The Saddest Country Songs of All Time Part 4
The Saddest Country Songs of All Time Part 5
17 More Sad Country Songs
Listen To Sad Country Songs
Country Artists Select Category 33 Years A Thousand Horses Aaron Lewis Aaron Watson Abi Ann Adam Craig Adam Doleac Adam Sanders AJ Gatio Alabama Alan Jackson Alana Amram Alee Alex Hall Alison Krauss Allie Louise Ally Lindeen Alyssa Micaela Amanda Lamb Amanda Watkins American Road American Young Amos Lee Amy Rose Anderson East Andrea Vasquez Angaleena Presley Anielle Reid Anthony Fallacaro Antigone Rising April Kry Ash Bowers Ashley Campbell Ashley Monroe Ashton Shepherd Asleep At The Wheel Aubrie Sellers Austin Lucas Austin Peckham Austin Webb Bailey Bryan Bart Crow Ben Haggard Ben Wells Beth Beighey Big & Rich Big City Brian Wright Big Smo Billy Currington Billy Gilman Billy Ray Cyrus Blackberry Smoke Blackhawk Blackjack Billy Blair Mathews Blaire Hanks Blake Shelton Bobby Bones & The Raging Idiots Boiling Point Brad Paisley Bradley Banning Bradley Walker Branch & Dean Brandon Hamilton Brandy Clark Brantley Gilbert Breelan Angel Brennin Brent Cobb Brett Eldredge Brett Kissel Brett Young Brian Collins Brian Keane Brian McComas Brianna Lauren Brodie Stewart Band Broken Halleluyah Brooke Ansley Brooke Eden Brooks & Dunn Broseph E. lee Brothers Osborne Brushville Bryan Kent Bryan White Buck 22 Bucky Covington Buddy Jewell Bush Hawg Caitlyn Smith Cale Dodds Cam Cameran Nelson Cameron Hawthorn Campbell Station Canaan Smith Candi Carpenter Carly Pearce Caroline Jones Carrie Underwood Casey Carpenter Casey Donahew Casey Donahew Band Casey James Cash Creek Cassadee Pope Charles Esten Charles Kelley Charlie Daniels Band Charlie Farley Charlie Faye Charlie Rich Charlie Rogers Charlie Worsham Chase Bryant Chase Rice Chasin Crazy Chelsea Gill Chris Bandi Chris Chitsey Chris Janson Chris Lane Chris Stapleton Chris Young Christian Kaser Christon Birge Chuck Wicks Cindy G Clare Bowen Clare Dunn Clay Walker Clayton Anderson Cledus T. Judd Clint Black CML Chart CML Graphics CML List Cody Canada And The Departed Cody Johnson Cody Webb Colbie Callait Cole Swindell Cole Taylor Collin Raye Colt Ford Confederate Railroad Corey Hager Corey Koehler Corey Smith Cory Michael Cory Morrow Country Artist Info Courtney Cole Cowboy Troy Craig Campbell Craig Morgan Craig Wayne Boyd Cross Canadian Ragweed Crowder Curtis Braly Curtis Grimes Dakota Bradley Dallas Davidson Dallas Smith Dan + Shay Dan Davidson Dan Fletcher Dan Seals Danielle Bradbery Darius Rucker Dark Ride Brothers Daryle Singletary Dave & Whitney Dave Barnes David Ball David Fanning David Harbaugh David Lee Murphy David Nail David Shelby Dean Alexander Dean Brody Deana Carter Dee Jay Silver Devin Dawson Dierks Bentley Dirk Powell Dixie Chicks Dolly Parton Don Henley Doug Adkins Doug Briney Doug Supernaw Downday Drake White Drew Baldridge Drew Moreland Dustin Lynch Dwight Yoakam Dylan Schneider Dylan Scott Easton Corbin Ed Sheeran Eddie Rabbitt Eileen Carey Electra Mustaine Eli Young Band Elizabeth Lyons Elle King Emily West Emmylou Harris Eric Church Eric Paslay Erik Dylan Faith Hill Falls Featured Filmore Fiona Culley First Aid Kit FJ Outlaw Florida Georgia Line Fort Defiance Frank Foster Frankie Ballard Freddy Fender Garth Brooks Gary Allan George Ducas George Jones George Strait Glen Campbell Glen Templeton Gloriana Gord Bamford Granger Smith Grant Maloy Smith Green River Ordinance Greg Finger Band Greg White Jr. Gretchen Wilson Gunner Scott Gwen Sebastian Haley & Michaels Haley Georgia Haley Zolup Hank Williams Jr. Hayley Orrantia Hayley Reardon Headline Hicks High Valley Holly Williams Home Free Homer Hart Hootie & The Blowfish Hosier Hoyt Hughes Huckleberry Hudson Moore Humming House Hunter Brothers Hunter Hayes Hunter Phelps Isaac Kenneth J Michael Harter Jackie Lee Jackson Michelson Jacob Colgan Jacob Davis Jake Owen James Barker Band James Otto James Robert Webb Jameson Rodgers Jamey Johnson Jamie Kent Jamie Lynn Spears Jamie O’Neal Jana Kramer Janelle Arthur Jared Hicks Jarrod Birmingham Jason Aldean Jason Kirkness Jason Michael Carroll Jason Mizelle Jason Sturgeon Jawga Boyz Jay Jolley Jay Matthes Jay Putty Jay Sparrow Jay Tighe JD & The Straight Shot Jeannine Barry Jebb Mac Band Jennifer Nettles Jenny Lewis Jerrod Niemann Jess And The Bandits Jessica Ridley Jessie James Decker Jessta James Jiggley Jones Jillian Jacqueline Jimmy Buffett JJ Lawhorn Jo Dee Messina Joanna Mosca Joe Bachman Joe Diffie Joe Nichols Joel Crouse Joel Wayne Joey + Rory Joey Feek Joey Hyde John and Jacob John Anderson John Berry John Conlee John Daly John Denver John King John Mayer John Mellencamp John Michael Montgomery John Oates John Timothy Johnny Cash JOHNNYSWIM Jolie Holliday Jon Pardi Jon Wolfe Jonathan Edwards Jordan Gray Jordan Prince Jordan Rager Josey Milner Josh Abbott Band Josh Dorr Josh Gallagher Josh Gracin Josh Grider Josh Kelley Josh Martin Josh Thompson Josh Turner Josh Ward Joshua Scott Jones JoSMITH Joy Styles JT Hodges Judah & The Lion Julia Sheer Julie C Myers Julie Roberts Justin Moore Justin Timberlake Justine Blazer Kacey Musgraves Kaitlyn Baker Kaitlyn Jackson Kalie Shorr Kandia Crazy Horse Kane Brown Karl Deeter Karli Whetstone Kate Brown Kate Russell Katie Armiger Kayla Adams Kayla Woodson Keith Urban Keith Walker Keith Whitley Kelleigh Bannen Kellie Pickler Kelly Clarkson Kelsea Ballerini Keni Thomas Kenny Chesney Kenny Rogers Kent Goolsby Kevin Costner & Modern West Kevin Fowler Kevin MaC Kevin McGuire Kezia Gill Kid Rock Kiefer Sutherland Kip Moore Kira Isabella Kree Harrison Kris Bradley Kristi Hoopes Kristian Bush Kristy Lee Cook Krystal Keith Kyle Park Kylie Hughes Lady Antebellum LANco Larry Peninsula Laura Bell Bundy Laura McCormick Lauren Alaina Lauren Flynn Leah Turner LeAnn Rimes Lee Ann Womack Lee Brice Lennon & Maisy Levi Hummon Levon Lexi James Lexi Larsen Lexi Lauren Lily Costner Lindsay Ell Lisa Matassa Lists Little Big Town Little Jimmie Dickens Little River Band Little Texas Locash LoCash Cowboys Logan Mize Lonestar Loretta Lynn Lori McKenna Lorrie Morgan Love And Theft Lucas Hoge Lucie Silvas Lucy Hale Luke Bryan Luke Combs M Callahan Mac McAnally Maddie & Tae Maddie And Tae Madeline Merlo Madelyn Victoria Maggie Rose Maggie Sajak Maiden Dixie Mandy Barnett Marc Daniels Maren Morris Margo Price Maria Taylor Marianne Allison Mario Flores Mark Chesnutt Mark Wills Markus Fox Marshall Dane Martina McBride Marty Stuart Mary Chapin Carpenter Mary Fletcher Matt Gary Matt Hundley Matthew O’Neill McBride And The Ride Meghan Linsey Mel Tillis Merle Haggard Michael Ray Michael Tyler Mickey Guyton Midland Mike Ryan Miranda Lambert Mitchell Tenpenny Mo Pitney Montgomery Gentry Moonshine Bandits Morgan Alexander Morgan Frazier Morgan Myles Morgan Wallen Natalie Hemby Natalie Stovall Natalie Stovall And The Drive Neal McCoy Neon Moon Nestor AnDress Nickel Creek Nikki Lane Nirvana Old Crow Medicine Show Old Dominion Old Southern Moonshine Revival Olivia Lane Owl City Pam Tillis Parker Millsap Parmalee Pat Green Pat McHenry Patty Loveless Pauline Andrès Pete Scobell Band Phil Vassar Post Monroe Pure Prairie League Rachael Turner Rachel Farley Rachel Holder Rachel Louise Taylor Rachel Timberlake Radney Foster RaeLynn Rainey Qualley Randy Houser Randy Rogers Randy Rogers Band Randy Travis Rascal Flatts Ray Johnston Band Ray Scott Reba McEntire Rebecca Stephens Reckless Kelly Restless Heart Rhiannon Giddens Rich O’Toole Rick Elliot Ricky Van Shelton Riley Smith Risa Binder River Town Saints Roadkill Ghost Choir Rodney Atkins Rodney Crowell Roger Jackson Ronnie Dunn Ronnie Milsap Runaway June Russell Dickerson Ruthie Collins Ryan Broshear Ryan Chrys & The Rough Cuts Ryan Follese Ryan Griffin Ryan Hurd Ryan Kinder Ryan Lafferty Ryan Robinette Sam Hunt Sam Rochford Sam Tio Samantha Landrum Sammy Arriaga Sammy Kershaw Sandra Lynn Sara Evans Sarah Darling Sarah Davidson Sarah Miles Sarah Ross Sasha McVeigh Sawyer Brown Scott Brothers Scott DeCarlo Scotty McCreery Seth Alley Seth Ennis Shane Lee Shania Twain SHeDAISY Shelley Lynch Shenandoah Sherry Lynn Sheryl Crow Shooter Jennings Sierra Hull Silverdrive 35 Sister C Sister Hazel Skip Ewing Sonia Leigh Sons Of Palomino Sons Of Vanity Southern Halo Stacy Burk Statesboro Revue Steel Blossoms Stephanie Quayle Stephen Hunley Stephen Wesley Steve Earle Steve Holy Steve Moakler Steve Wariner Steven Lee Olsen Steven Martinez Steven Tyler Stevenson Everett Stoney LaRue Striking Matches Strugill Simpson Sturgill Simpson Sugarland Sundance Head Sundy Best Sunny Sweeney Suzy Bogguss Sweet Home Symphony T.G. Sheppard Tanya Marie Harris Tara Thompson Tate Stevens Taylor Acorn Taylor Swift Temecula Road Tenille Arts Terri Clark The Band Perry The Cadillac Three The Cains The Cains Trio The Civil Wars The G Brothers The GetBye The Grahams The Henningsens The Hobbs Sisters The Infamous Stringdusters The Joseph Sisters The Lacs The Last Bandoleros The Orchard The Railers The Rebel Light The Shires The Swon Brothers The Wild Feathers Thomas Rhett Thompson Square Tim Ash Tim Dugger Tim McGraw Timothy Ryan Toby Keith Tom O’Connor Tommy Steele Band Tony Garcia Trace Adkins Tracy Byrd Tracy Chapman Tracy Lawrence Trailer Choir Travis Tritt Trent Harmon Trent Tomlinson Trisha Yearwood Truth & Salvage Co Tucker Beathard Turnpike Troubadours Ty Herndon Tyler Dial Tyler Farr Tyler Joel Tyler Reeve Uncle Kracker Vanity Vern Gosdin Vince Gill Wade Bowen Wade Hayes Walker Hayes Walker McGuire Ward Thomas Waterloo Revival Wes Mack Western Avenue Weston Burt Whiskey Myers Whitney Wolanin Wild Ponies Will Hoge William Clark Green William Michael Morgan Willie Nelson Wynonna Zac Brown Band Zane Williams Zarah Strong
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