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Kristoffer Kristofferson is a retired American singer, songwriter and actor. Among his songwriting credits are "Me and Bobby McGee", "For the Good Times", "Sunday Mornin' Comin' Down", and "Help Me Make It Through the Night", all of which were hits for other artists.

Harold Lloyd Jenkins, better known by his stage name Conway Twitty, was an American singer and songwriter. Initially a part of the 1950s rockabilly scene, Twitty was best known as a country music performer. From 1971 to 1976, Twitty received a string of Country Music Association awards for duets with Loretta Lynn. He was inducted into both the Country Music and Rockabilly Halls of Fame.

David Allan Coe is an American singer and songwriter. Coe took up music after spending much of his early life in reform schools and prisons, and first became notable for busking in Nashville. He initially played mostly in the blues style, before transitioning to country music, becoming a major part of the 1970s outlaw country scene. His biggest hits include "You Never Even Called Me by My Name", "Longhaired Redneck", "The Ride", "Mona Lisa Lost Her Smile", and "She Used to Love Me a Lot".

George Glenn Jones was an American country musician, singer, and songwriter. He achieved international fame for his long list of hit records, including his best-known song "He Stopped Loving Her Today", as well as his distinctive voice and phrasing. For the last two decades of his life, Jones was frequently referred to as the greatest living country singer. Country music scholar Bill Malone writes, "For the two or three minutes consumed by a song, Jones immerses himself so completely in its lyrics, and in the mood it conveys, that the listener can scarcely avoid becoming similarly involved." The shape of his nose and facial features earned Jones the nickname "The Possum". Jones has been called "The Rolls-Royce of Country Music" and had more than 160 chart singles to his name from 1955 until his death in 2013.

Jamieson "Junior" Brown is an American country guitarist and singer. He has released twelve studio albums in his career, and has charted twice on the Billboard country singles charts. Brown's signature instrument is the "guit-steel" double neck guitar, a hybrid of electric guitar and lap steel guitar.

Randall Hank Williams, known professionally as Hank Williams Jr. or Bocephus, is an American singer-songwriter and musician. His musical style is often considered a blend of southern rock, blues, and country. He is the son of country musician Hank Williams and the father of musicians Holly Williams and Hank Williams III.

Gary Ronnie Stewart (May 28, 1944 – December 16, 2003) was a country musician and songwriter known for his distinctive vibrato voice and his southern rock influenced, outlaw country sound. During the peak of his popularity in the mid-1970s, Time magazine described him as the "king of honkytonk." He is remembered for a series of country chart hits from the mid- to late- 1970s, his biggest hit being "She's Actin' Single (I'm Drinkin' Doubles)," which topped the U.S. country singles chart in 1975.

Named after actor Gary Cooper, Stewart was born in the Letcher County, Kentucky, town of Jenkins, the son of George and Georgia Stewart. In 1959 his father, a coal miner, sustained an injury while working in the mines, and shortly afterwards the family moved to Fort Pierce, a city on Florida's Atlantic coast.

Billy Joe Shaver (August 16, 1939 – October 28, 2020) was an American outlaw country singer and songwriter, as well as an actor.

Shaver was born in Corsicana, Texas, and raised by his mother, Victory Watson Shaver. Until he was 12, he spent a great deal of time with his grandmother in Corsicana, so his mother could work in Waco. He sometimes accompanied his mother to her job at a local nightclub, where he began to be exposed to country music.

Shaver's mother remarried about the time that his grandmother died, so his older sister Patricia and he moved in with their mother and new stepfather. Shaver left school after the eighth grade to help his uncles pick cotton, but occasionally returned to school to play sports.

Merle Ronald Haggard was an American country music singer, songwriter, guitarist, and fiddler.

Martin David Robinson, known professionally as Marty Robbins, was an American singer, songwriter, actor, multi-instrumentalist, and NASCAR racing driver. Robbins was one of the most popular and successful country and western singers for most of his nearly four-decade career, which spanned from the late 1940s to the early 1980s. He was also an early outlaw country pioneer.

Thomas T. Hall (born May 25, 1936) is an American country music songwriter, singer, instrumentalist, novelist, and short-story writer. He has written 12 No. 1 hit songs, with 26 more that reached the Top 10, including the No. 1 international pop crossover smash "Harper Valley PTA" and the hit "I Love," which reached No. 12 on the Billboard Hot 100. He is included in Rolling Stones list of 100 Greatest Songwriters. He became known to fans as "The Storyteller," thanks to his storytelling skills in his songwriting.

Hall was born in Olive Hill, Kentucky, United States. As a teenager, he organized a band called the Kentucky Travelers that performed before movies for a traveling theater. During a stint in the Army, Hall performed over the Armed Forces Radio Network and wrote comic songs about Army experiences. Following his time in the army he used the G.I. Bill program to enlist in Roanoke College, where he worked as a disc jockey. His early career included being a radio announcer at WRON, a local radio station in Ronceverte, West Virginia. Hall was also an announcer at WMOR 1330AM in Morehead, Kentucky. Hall was also an announcer at WSPZ, which later became WVRC Radio in Spencer, West Virginia, in the 1960s.

The Highwaymen were an American country music supergroup, composed of four of country music's biggest artists who pioneered the outlaw country subgenre: Johnny Cash, Waylon Jennings, Willie Nelson, and Kris Kristofferson. Between 1985 and 1995, the group recorded three major label albums as The Highwaymen: two on Columbia Records and one for Liberty Records. Their Columbia works produced three chart singles, including the number one "Highwayman" in 1985.

Johnny Paycheck was an American country music singer and Grand Ole Opry member notable for recording the David Allan Coe song "Take This Job and Shove It". He achieved his greatest success in the 1970s as a force in country music's "outlaw movement" popularized by artists Hank Williams Jr., Waylon Jennings, Willie Nelson, Billy Joe Shaver, and Merle Haggard. In 1980, Paycheck appeared on the PBS music program Austin City Limits. But during that decade, his music career slowed due to drug, alcohol, and legal problems. He served a prison sentence in the early 1990s and his declining health effectively ended his career in early 2000. In autographs, Paycheck signed his name "PayCheck".

Robert Joseph Bare Sr. (born April 7, 1935) is an American country music singer and songwriter, best known for the songs "Marie Laveau", "Detroit City" and "500 Miles Away from Home". He is the father of Bobby Bare Jr., also a musician.

In the 1950s, Bare repeatedly tried and failed to sell his songs. He finally got a record deal, with Capitol Records, and recorded a few unsuccessful rock and roll singles. Just before he was drafted into the United States Army, he wrote a song called "The All American Boy" and did a demo for his friend, Bill Parsons, to learn how to record. Instead of using Parsons' later version, the record company, Fraternity Records, decided to go with Bare's original demo. The record reached No. 2 on the Billboard Hot 100, but Fraternity erroneously credited Bill Parsons on the label. The same track, with the same billing error, peaked at No. 22 in the UK Singles Chart in April 1959. In 1965, an album of older recorded material, Tender Years (JM-6026), was released on the Hilltop label. That same year, the material was repackaged by Sears and released under the title Bobby In Song (SPS-115). These albums are not usually included in Bare's published discographies.

John Marty Stuart is an American country and bluegrass music singer, songwriter, and musician. Active since 1968, Stuart initially toured with Lester Flatt, and then in Johnny Cash's road band before beginning work as a solo artist in the early 1980s. His greatest commercial success came in the first half of the 1990s on MCA Records Nashville. Stuart has recorded over 20 studio albums, and has charted over 30 times on the Billboard Hot Country Songs charts. His highest chart entry is "The Whiskey Ain't Workin'", a duet with Travis Tritt. Stuart has also won five Grammy Awards out of 16 nominations. He is known for his combination of rockabilly, country rock, and bluegrass music influences, his frequent collaborations and cover songs, and his distinctive stage dress. Stuart is also a member of the Grand Ole Opry and Country Music Hall of Fame.

Loretta Lynn (née Webb; April 14, 1932) is an American singer songwriter. In a career which spans six decades in country music, Lynn has released multiple gold albums. She is famous for hits such as "You Ain't Woman Enough (To Take My Man)", "Don't Come Home A-Drinkin' (With Lovin' on Your Mind)", "One's on the Way", "Fist City" and "Coal Miner's Daughter" along with the 1980 biographical film of the same name.

Lynn has received numerous awards and other accolades for her groundbreaking role in country music, including awards from both the Country Music Association and Academy of Country Music as a duet partner and an individual artist. She has been nominated 18 times for a GRAMMY Award, and has won 3 times. Lynn is the most awarded female country recording artist and the only female ACM Artist of the Decade (1970s). Lynn has scored 24 No. 1 hit singles and 11 number one albums. She ended nearly 50 years of touring on the road after she suffered a stroke in 2017 and then broke her hip in 2018.