Remembering The Country Music Icons We Lost In 2020

Joe Diffie, Charley Pride, John Prine are posing for a picture

It’s was a tough year for just about everyone, but the country music community was hit especially hard in 2020.

While we look forward to a better year in 2021, it’s also a good time to reflect back on 2020 and remember all it has taken a lot from us. Singer, songwriters, reporters, radio show hosts, band members, and many others who impacted country music positively have gone as well.

This is by no means a comprehensive list of everybody that we lost this year, but a chance to celebrate the lives of some of the more notable musicians who have died this year. Here are a few of their greatest songs to remember them by.

Paul English – February 11, 2020 (87)

The only musician included on this list who didn’t make his own music, Paul English spent his career playing the drums in Willie Nelson’s band. Playing with Nelson for the first time in 1955, English also played with Blues musician Delbert McClinton until joining Willie Nelson’s band full time in 1966. A real outlaw with a criminal past in his younger days, English also acted as a bodyguard and bookkeeper for Nelson when they were on tour, and would sometimes have to take matters into his own hands to make sure they received fair compensation from promoters and venues. The two were also best friends, and went through a lot together over the years. Paul English is one of the most iconic country music drummers of all time.

English was also one of the original four members of the Farm Aid board of Directors, along with Willie Nelson, John Mellancamp and Neil Young in 1985. English would go on to serve as treasurer for the organization for many years as well.

Kenny Rogers – March 20, 2020 (81)

Known for “The Gambler” and the Dolly Parton duet “Islands in the Stream,” Kenny Rogers had a long and legendary career in country music.

“Lucille” – Kenny Rogers (1976)

One of the best songs to come out of the ’70s, Rogers killed it with this one.

Jan Howard – March 28, 2020 (91)

Jan Howard hadn’t considered a career in music until she met Harlan Howard, a country music songwriter, in 1957 at 28 years old. Harlan, who she ended up marrying, discovered that she could sing and helped her get the opportunity to record some demos. The rest was history, as Howard became a member of the Grand Ole Opry and recorded a number of hits throughout the 60s and 70s.

“The One You Slip Around With” (1959)

“My Son” – Jan Howard (1969)

“My Son” was released as a single in 1968 before being included on Howard’s self-titled album in 1969. Originally written by Howard as a letter to her son who was serving in the Vietnam War, she subsequently put music to it and recorded it in one take.

Joe Diffie – March 29, 2020 (61)

An absolute 90’s country legend with one of the greatest mullets the genre has ever seen, The Pickup Man recorded a number of classics.

“John Deere Green” – Honkey Tonk Attitude (1993)

Billy Bob and Charlene, the greatest love story country music has ever seen.

“Bigger Than the Beatles” – Life’s So Funny (1995)

“Prop Me Up Beside the Jukebox (If I Die)” – Honkey Tonk Attitude (1993)

Doesn’t get much more 90s than this Diffie song. Incredible music video too.

John Prine – April 7, 2020 (73)

One of the greatest songwriters across any genre, John Prine was included on Rolling Stone’s “The 100 Greatest Songwriters of All Time” list. His ability to write from different perspectives, like in “Angel from Montgomery,” have influenced tons of other musicians.

“Fish and Whistle” – Bruised Orange (1978)

Charlie Daniels – July 6, 2020 (83)

With music spanning southern rock, country, and bluegrass, Charlie Daniels did it all, and he was good at it too. One of the greatest fiddle players of all time, his impact on the country genre has been unfathomable.

“Sweetwater, Texas” – Saddle Tramp (1973)

The most underrated Charlie Daniels Band song, “Sweetwater, Texas” tells a great story of small town love and loss.

“Devil Went Down to Georgia” – Million Mile Reflections (1979)

One of the greatest songs of all time, legendary stuff from a legendary person. If you don’t get goosebumps when Johnny says, “Devil, just come on back if you ever wanna try again
I done told you once–you son of a bitch–I’m the best there’s ever been,” then something might be wrong with you.

We need more fiddle like this in country music.

Justin Townes Earle – August 20, 2020 (38)

Known primarily for being the son of Steve Earle, Justin Townes Earle had an incredible career as a musician in his own right. At only 38 years old, he had a long career ahead of him too.

“Far Away in Another Town” – The Good Life (2008)

“Turn Out My Lights” – The Good Life (2008)

“Harlem River Blues” – Harlem River Blues (2010)

Jerry Jeff Walker – October 23, 2020 (78)

A contemporary of many of the all time greats on Austin’s outlaw country scene in the 1970s, Jerry Jeff Walker helped pave the way for the Texas music scene we all love today. His song “Mr. Bojangles” may be one of the most underrated songs of all time, influencing musicians for decades.

“Mr. Bojangles” – Mr. Bojangles (1968)

Another one of the greatest songs of all time, “Mr. Bojangles” was originally written and recorded by Jerry Jeff Walker in 1968 before the Nitty Gritty Dirt Band popularized it with a cover in 1970. Dozens of other artists have recorded and performed it as well. The song tells a true story of a homeless street performer Walker met in jail, who called himself Mr. Bojangles to keep his real identity from police. Mr. Bojangles told stories about travelling with his dog and tap danced for others in the cell.

“Pissin’ in the Wind” – Ridin’ High (1975)

You know Walker and his buddies had a good time recording this classic.

“London Homesick Blues” – Viva Terlingua (1973)

Billy Joe Shaver – October 28, 2020 (81)

A real life outlaw, Billy Joe Shaver was perhaps the most instrumental figure on the outlaw country scene, yet he still managed to fly under the radar. Throughout his career he wrote that were recorded by Waylon Jennings, Johnny Cash, Kris Kristofferson, Johnny Paycheck, and more.

“I Been to Georgia on a Fast Train” – Billy Joe Shaver (1982)

“Live Forever” – Tramp on Your Street (1993)

Co-written with his son Eddy Shaver who died in 2000 of an overdose, this song is especially emotional now that both of its writers have passed.

“Honky Tonk Heroes” – Honky Tonk Heroes (By Waylon Jennings) (1973)

With the exception of one song, Billy Joe Shaver wrote this entire Waylon album. Waylon had invited him to come write for him in Nashville, but by the time Shaver had arrived, Jennings had forgotten about the invitation. After six months of trying to see Waylon to confront him, Shaver found him in an RCA recording studio and threatened to fight him if Waylon didn’t listen to his songs.

After talking for a little bit, Waylon agreed he’d listen to Shaver’s songs, and if he liked it he’d record it. As soon as there was a song he did not like, though, Shaver had to leave. Waylon subsequently came to find that he loved them all, and the rest is history. A truly remarkable encounter that changed both Shaver’s and Waylon’s life.

Hal Ketchum – November 23, 2020 (67)

Hal Ketchum was a force to be reckoned with in the 90s, releasing five albums throughout the decade, and four more over the following 15 years.

“Small Town Saturday Night” – Past the Point of Rescue (1991)

A ’90s anthem.

“Hearts are Gonna Roll” – Sure Love (1992)

“Past the Point of Rescue” – Past the Point of Rescue (1991)

Charley Pride – December 12, 2020 (86)

A true trailblazer, Charley Pride is a country music hall-of-famer and one of three African-American members of the Grand Ole Opry. Born to poor sharecroppers in Mississippi, Pride overcame the odds and found success in a predominantly white industry.

Pride’s first love was baseball though, playing in the Negro Leagues and Minor Leagues for most of the 1950s. In 2008, he was drafted to the Colorado Rockies in a draft to commemorate former Negro Leaue players.

“Kiss an Angel Good Mornin’” – Sings Heart Songs (1971)

One of the greatest country love songs ever.

“Roll on Mississippi” – Roll on Mississippi (1981)

An ode to the Mississippi River.

“Is Anybody Goin’ to San Antone” – Charley Pride’s 10th Album (1971)

K.T. Oslin – December 21, 2020 (78)

Oslin experienced most of her success in the 1980s, releasing a number of high-charting hits and receiving a total of nine CMA, ACM, and Grammy awards between 1987-1989. Before finding success as a solo artist, Oslin dabbled in acting and even performed alongside legend Guy Clark and David Jones in a trio that recorded an album but never released it.

“Hey Bobby” – This Woman (1987)

“Hey Bobby” is one of the most popular songs off of Oslin’s Grammy Award-winning album.

“Come Next Monday” – Love in a Smalltown (1990)

“80’s Ladies” – 80’s Ladies (1987)

One of her biggest hits, “80’s Ladies” helped Oslin win a 1987 ACM award for video of the year, 1988 CMA award for song of the year, and 1988 Grammy Award for Best Country Vocal Performance by a female.

Tony Rice – December 25, 2020 (69)

Revered by many as the best acoustic guitarist of all time, Tony Rice is an absolute bluegrass legend, and has influenced countless musicians we all listen to today. Rice played with a number of bands including J.D. Crowe and the New South, and has played alongside all time greats like the Grateful Dead’s Jerry Garcia. Here are a few of the best solo songs he released throughout his career, but watch any video of Tony Rice playing the guitar and his picking will speak for itself.

“Church Street Blues” – Church Street Blues (1993)

“Why You Been Gone So Long” – Native American (1988)

“Cold on the Shoulder” – Cold on the Shoulder (1984)

A beer bottle on a dock



A beer bottle on a dock