Country Singers That Know Pain

Updated: Oct 11

Three chords and the truth is probably the most precise or perfect definition of country music. And it came from a man that was not schooled in the traditional sense of the term, but grew up listening to the Grand Ole Opry. Of course, I'm talking about Harlan Howard, who said that sad songs always beckoned him. I feel the same. Harlan liked those tear jerking, cry in your beer songs far more than the typical boy meets girl tunes. Some would even say he was as much a Hillbilly Poet as Hank Williams. 

Though I could certainly fill up an encyclopedia with just Harlan’s accomplishments this blog post is not about Harlan at all. It’s about how unironically truthful his definition of country music was, and is still today. I was listening to Matt Carson, who has an album coming out titled “Three Chords, And The Truth”. It made me think about how many of our artists have gone through hell, and back. Some fortunate to live, and tell, and others not so much.

I think the anniversary of Patsy, Cowboy Copas, and Hawkshaw Hawkins death in the same week as the devastating Nashville tornadoes really made me think about how tomorrow is not promised to anyone. I recalled reading about how one of my favorite actors studied Method acting. The approach is you throw yourself into the life that your character lives in order to accurately represent the character. 

I think with country music it’s the other way around. You feel hurt, loss, heartbreak, cry which leads to pouring your heart onto white spaces. The fans come along for the ride because you are singing about their lives too. Who hasn’t had a broken heart?  What follows is a list of five artists that have gone through hell! And much like real life, it’s not always a happy ending.

  • George Strait

Few can match the success King George enjoys even today. His career spans 33 years. Mr. Strait has earned 60 No. 1 songs (so far). That is more than any performer in history!  From the outside looking in, his life looks pretty darn good. However, George can certainly speak to tragedy. 

When George was in third grade, his mother took his sister, and left both George, and his brother behind with their father. He was raised in a God-fearing home, and learned early to depend on God’s direction concerning his life.

He married his highschool sweetheart Norma, who encouraged him to continue with music even when he wasn’t getting anywhere. Believe it or not, in 1990 with no record deal in sight, George was ready to leave the music business altogether. Fortunately, Norma convinced him to give it one more year, and low, and behold in 1981, he was signed to MCA Records.

Things were going great! George was finally generating the success, he worked so hard for. On the heels of his Top Male Vocalist win at the ACM, and CMAs, an unexpected turn of events sent the Strait family reeling with pain.

On June 25, 1986, Jennifer Lynn Strait was killed in a car accident caused by the 18 year old driver. She was riding with two other friends. Jennifer was only 13 years, the accident was not alcohol related. Though George kept performing, it took him 21 years to publicly talk about the tragic loss!

Fast forward on Aug 31.2018, George lost Mike Kennedy. Mike played drums for Mr. Strait for 30 years as a member of the Ace in the Hole Band. George said he could not express how deeply Mike’s loss was felt.

Mr. Strait has known how to learn from the experience of loss. George pays homage to his daughter with the Jenifer Strait Memorial Foundation It helps organizations such as St. Jude’s Ranch, Boys and Girls Club of San Antonio, and Carver Academy to help their local communities.


Outliving your child is heartbreaking.. Here’s a song George recorded that is a tribute to his daughter.. My favorite line in the song is “I’ve never seen a hearse with a luggage rack".

  • Tammy Wynette

“I believe you have to live the songs..”

How do you begin a paragraph on Tammy Wynette? Her life was tragic from the very beginning. Her dad died of a brain tumor when she was an infant. Her mother took a job in Memphis, and left Tammy with her grandparents. Tammy was married before her 18th birthday, the first of five marriages.


Her youngest daughter Tina was born with spinal meningitis. Tina spent seven weeks in the hospital with a slim chance of surviving, but she did survive, and was nicknamed the miracle baby. When Tammy shared her dreams of becoming a country singer with her husband, he told her to "Dream on baby".

She left her first husband and was now a single mother in the 1950’s Cleaver family era. Tammy supported her kids as a hairdresser, and worked nights as a nightclub singer in the deep south. If that is not a testament to strength or inner resolve, I don’t know what is. As tragic as all of this sounds, it was just the beginning.

She remarried, but allegations of domestic abuse loomed large. Her second husband, Don Chapell, a respected songwriter that wrote songs for George, Conway, and many others shared nude pictures of Tammy without her consent, and routinely humiliated her in front of others. One evening, while George was visiting Tammy and Don’s home, they started fighting. George interceded, and took Tammy away from Don that same night.

But George Jones was also not quite the knight in shining armor. Together Tammy and George would record many hit songs, but, as I’ve always said sometimes what starts badly ends worse. On “Tales From The Tour Bus”, it is alleged that Tammy divorced super star George Jones after years of on, and off again breakups centered around George’s well documented drinking binges. 

The straw that broke the proverbial camel’s back was when George chased Tammy around the house with a loaded shotgun. Some reports state shots were actually fired. Who knows, the bottom line is Tammy had enough, and filed for divorce.

But, if you thought somehow things got better for Tammy after George, well no.. Her fourth marriage lasted less than 60 days. And things got really weird with her fifth marriage. Firstly, there was the mysterious kidnapping that took place. On October 4th, 1978, Tammy was allegedly kidnapped at gunpoint from a Nashville mall, driven 80 miles out, beaten, and left to die. But the details of the story never seemed to add up. 

 In 2000 Jackie Daily revealed in a memoir that her mother confided in her that her fifth husband, George Richey had beaten her. Tammy created the abduction story to explain away the bruises, and fractured cheekbone she suffered. Eventually, Tammy’s daughters filed a wrongful death suit against Richey, and Tammy’s body was exhumed. The case was eventually settled out of court, but the details, and authenticity of the alleged kidnapping still remain a mystery.

In Tammy’s last years she had a hysterectomy, and had part of her stomach removed. She also developed a dependency on painkillers. Some reports state she forgot words to songs, and sometimes nodded off in between songs while still onstage. Yet more, and more concerts were booked. George Richey, her last husband was also her manager. Tammy died on April 6 1998 of heart failure, she was only 55.

Here is Tammy’s iconic song “I Don’t Want To Play House”, which deals with the heartbreak of divorce, and the effect it can have on a child.

Steve Earle 

It seems like eons ago since the hardcore troubadour Steve Earle had his run in with drug addiction, and the law. Steve Fain Earle cut his teeth playing dive bars in Texas. He finally touched down in Nashville with the intention of recording his first album by his 21rst birthday.. He was just a little off by oh 10 years. He had gotten a couple of album cuts early on. The most notable being “The Devil’s Right Hand” which was recorded by Waylon Jennings!

Though no one could deny Steve Earle’s talent, many of his songs were not the type that most artists could record other than him. The quintessential Guitar Town, Exit O, and Copperhead Road years propelled Steve to cult status, but addiction took over, and he did not write a lick for several years. The early 90's consisted of a lot of repackaged Steve Earle material, mostly collections, and a live album.

In an interview with the Chicago Tribune, Steve confides: ”I would clean up and be sick for three days before we went out on the road."

He would sell everything he could fit into his car to fund his habit. At one point his addiction got so bad that he was using the cars of his friends just to have someplace to sleep for the night. He was spending about $1000 a day on heroin. He switched to cocaine, and the methadone clinic when he failed to get high enough.

In 1993, he was arrested for possession of heroin, and in 1994 for possession of cocaine. There was also a firearm charge. He was sentenced to a year in jail. Fortunately, he served only 60 days, and was ordered to a rehab center. It literally saved his life. The first album he ever recorded sober, and drug free was “A Train a’ Comin”. 

Steve Earle has since earned three Grammys, and is the host of the popular Hardcore Troubadour show on Sirius XM. He is also a passionate supporter of Autism research, and holds an annual benefit named after his son John Henry. I think the following song really speaks to the darker days of Steve's past addiction struggles.

Dottie West

Few women in country music have had the impact Dottie West had. A vocal stylist, and songwriter. Her career spanned nearly three decades. She received a Grammy, CMA, and multiple BMI awards. She also received the coveted CLIO award for excellence in advertising. Coca Cola even signed her to a lifetime contract as a jingle writer based on the success of the” Country Sunshine” campaign. I’ve included the commercial below. Dottie remained one of the most popular Grand Ole Opry members for the entirety of her career. Her accomplishments are nearly unbelievable when you discover the unspeakable tragedies in her life.

Dottie was born Dorothy Marsh in Frog Pond, TN. Her family was very poor. Her father was an alcoholic who beat, and raped Dottie. Finally, when she was 17 years old, she turned him in, he was given a 40 year sentence. He died in jail. 

After several failed attempts at securing a record contract in Ohio with her husband Steel Guitar player Bill West, they moved to Nashville. They were befriended by a group of young artists trying to make it in the Music City. Among the group were Willie Nelson, Roger Miller, Harlan Howard, and Patsy Cline.

Though they were readily accepted into the music community, times were tough. Patsy who was already experiencing massive success helped pay their rent, and groceries. Dottie, and Patsy became friends. On March 3, 1963, Dottie attended the benefit in Missouri for a popular Dj Cactus Jack who had passed on. Dottie, and Roy Acuff were slated to perform, but canceled at the last minute. Dottie said Patsy looked like an angel at her last performance wearing a white chiffon dress. She sounded better than ever, and the crowd absolutely adored her.

 It was rainy, dreary weather. No clearance was given for flight. Dottie invited her to ride with them back to Nashville.. She almost did, but decided to charter a plane instead as she was really missing her kids, and wanted to get back to them as soon as possible. Can you imagine what must have run through Dottie’s mind when on March 5th, 1963 Dottie heard that Patsy had died.. Tragic..

Dottie continued to chart, and perform to well received shows through the 80’s, but it was not enough to support her lavish lifestyle. When 1990 rolled around Dottie had been sued by her then husband, her current manager, and her ex manager. Furthermore, the bank foreclosed on her mansion, and sent her an eviction notice. If you think it couldn’t get any worse, well you are wrong.


The IRS liquidated all her tangible assets including her awards. She owed them 1.3M in back taxes. In 1991, the dust started to settle, and Dottie was in the planning stages of her comeback, which entailed a duet album with some of her closest friends: Tanya Tucker, Roger Miller, and Kenny Rogers to name a few. But tragedy would strike a final blow.


On August 30, 1991, Dottie left her apartment, and was driving to the Opry to do a show in a car Kenny Rogers had gifted. The car stalled, and her elderly neighbor stopped to help. Running behind, Dottie urged the driver to go quickly. He lost control of the car mere minutes from Opryland.

The first responders, and Dottie assessed the elderly man as needing immediate attention. No one knew that Dottie had several internal injuries such as a lacerated liver. Kenny Rogers visited her while she was in the hospital. Several operations were done. She died on the operating table on Sept 4th, 1991.

Eddie Montgomery

Talent runs in them genes! Eddie was born in Danville, KY, and played drums in his father’s band. John Michael Montgomery who is his brother, and Troy Gentry played together in the Early Tymz Band, and again in the Young Country band. Troy Gentry left to pursue a solo career, and actually won the Jim Beam National Talent Contest. With no record label in hand, he joined forces again with Eddie.

Things were going pretty good after ten years of hits, and Eddie had a rock solid marriage of twenty years! In 2010, Eddie was diagnosed with prostate cancer, and his wife filed for divorce the same month. Eddie was served with divorce papers at a steakhouse, no pun intended. 

The restaurant he opened with his now ex wife failed leaving Eddie saddled with millions of dollars of unrecoverable debt. He eventually filed for bankruptcy in 2014. He also got married to his current wife that year, but within days his house was hit by a tornado! Oh, he also lost his record deal with Sony Nashville.

On September 27, 2015, Eddie’s son died after being on life support for several days. Eddie Montgomery’s ex-wife Tracy first denied rumors of a drug overdose. She later recanted her previous statement, and confirmed that the death was due to an accidental drug overdose. It was suspected that Hunter was experimenting with synthetic marijuana. He was only 19, and left a 4 month old infant behind. Parents never want to outlive their children. The utter devastation that a person must feel is unimaginable.

The type of success that Montgomery Gentry earned is what artists dream about. Three platinum records, countless charted hits, a Grand Ole Opry membership, life was good. Now on Colt Ford’s record label Average Joe Entertainment, they were touring, and putting out new music for the fans.


Life however took another unanticipated turn. On September 8th, 2017, Troy took a helicopter ride in Medford, NJ. Montgomery Gentry were slated to play that evening. He never made it. “It was a horrific day, my world changed as much as the band did”. Montgomery said. "It’s something that you never get over. It’s going to be in my mind and my soul for the rest of my life.”


Here's a classic they took to #1 written by one of my favorite songwriters Chris Knight.

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