Country Masterpieces

"Stand by Your Man" (Tammy Wynette, 1968) — Ranked No. 1 on the CMT Greatest Country Songs list. Recorded with Billy Sherrill as producer, Pete Drake on steel guitar, and Jerry Kennedy on guitar, this classic Nashvillian production captures powerful emotional and domestic themes with its human immediacy.
"He Stopped Loving Her Today" (George Jones, 1980) — Ranked No. 2 on the CMT list. Widely praised as the greatest country song ever written, Jones' landmark comeback single features Pete Drake's steel guitar, Pig Robbins' piano, and Charlie McCoy's harmonica.
"Crazy" (Patsy Cline, 1961) — Ranked No. 3 on the CMT list. Written by Willie Nelson in 1961 during a car journey from Houston to Nashville, the song was originally titled "Stupid". Patsy Cline recorded it the week after Nelson woke her up in the middle of the night to sing it to her, leading to it becoming the most popular jukebox song of all time.
"Ring of Fire" (Johnny Cash, 1963) — Ranked No. 4 on the CMT list. Written by June Carter and Merle Kilgore about the consuming, wild flames of love. Cash decided to add Spanish-style mariachi horns to the arrangement after the idea came to him in a dream.
"Your Cheatin' Heart" (Hank Williams, 1953) — Ranked No. 5 on the CMT list. Hank Williams drafted the lyrics in ten minutes during a drive to Louisiana with his fiancée, Billie Jean Jones, as he reflected on his ex-wife Audrey's behavior. Williams recorded it during his final studio session in 1952 shortly before his untimely death.
"Friends in Low Places" (Garth Brooks, 1990) — Ranked No. 6 on the CMT list. Written by Earl Bud Lee and Dewayne Blackwell after Lee forgot his wallet at lunch and joked about having "friends in low places". Originally written on paper napkins, it became a massive country music phenomenon.
"Mamas Don't Let Your Babies Grow Up to Be Cowboys" (Waylon Jennings & Willie Nelson, 1978) — Ranked No. 10 on the CMT list. Ed and Patsy Bruce initially wrote this song as "guitar players" before changing the focus to "cowboys" due to the iconic status of Western films. Waylon and Willie recorded their defining duet in 1978.
"Coal Miner's Daughter" (Loretta Lynn, 1970) — Ranked No. 13 on the CMT list. Written by Lynn in 1969 to tell her own hardscrabble personal story. It utilized a shifting, modulating melody and served as the title track for a movie that won an Academy Award.
"The Dance" (Garth Brooks, 1990) — Ranked No. 14 on the CMT list. Written by Tony Arata as an elegant comment on the human condition, the song's music video serves as a tribute to those who sacrificed their lives for what they believed in, featuring archival footage of figures like Martin Luther King Jr., the Challenger crew, Lane Frost, and John F. Kennedy.
"Folsom Prison Blues" (Johnny Cash, 1956) — Ranked No. 25 on the CMT list. Composed by Cash in 1953 while serving in Germany with the US Air Force, the song was inspired by the film Inside the Walls of Folsom Prison. It featured the legendary line "I shot a man in Reno just to watch him die," which caused controversy and was temporarily removed from radio edit play after Robert F. Kennedy's assassination.
"Fancy" (Reba McEntire, 1991) — Ranked No. 27 on the CMT list. A mini-movie video that details a rags-to-riches story of rural poverty, maternal desperation, and survival.
"I'm So Lonesome I Could Cry" (Hank Williams, 1949) — Ranked No. 29 on the CMT list. This B-side utilized Zeke Turner's electric guitar, Jerry Byrd's steel guitar, and Tommy Jackson's fiddle to construct a bleak, melancholic atmosphere focused on profound isolation.
"I Walk the Line" (Johnny Cash, 1956) — Ranked No. 31 on the CMT list. Written as a promise of fidelity on the road while Cash toured with Elvis Presley. The track starts with an eerie drone that Cash discovered by accident while playing back a tape in reverse while in the military.
"Breathe" (Faith Hill, 2000) — Ranked No. 38 on the CMT list. This song depicts the feeling of being in a lover's arms. Its music video drew controversy for shots of Hill laying in a silk-sheeted bed.
"Kiss an Angel Good Mornin'" (Charley Pride, 1971) — Ranked No. 58 on the CMT list. Led by Pride's warm, smooth vocals, this 1971 track served as a massive crossover hit that helped overcome racial barriers in country music.
"Family Tradition" (Hank Williams Jr., 1979) — Ranked No. 59 on the CMT list. Written as a rowdy anthem by Hank Jr. to redefine his image following a near-fatal mountain fall in Montana.
"There Stands the Glass" (Webb Pierce, 1953) — Ranked No. 68 on the CMT list. A classic honky-tonk anthem featuring a prominent sawdust-on-the-floor, sharp whiskey vibe.
"A Boy Named Sue" (Johnny Cash, 1969) — Ranked No. 72 on the CMT list. A poem written by Shel Silverstein that Cash recorded live without rehearsal at San Quentin Prison in 1969.
"Strawberry Wine" (Deana Carter, 1996) — Ranked No. 75 on the CMT list. Tells the story of young summer love, strong and steamy, then gone too soon.
"She's in Love With the Boy" (Trisha Yearwood, 1991) — Ranked No. 80 on the CMT list. Story of Katie and Tommy who fall in love despite parents' wishes, eventually finding acceptance.

Blues, Soul, and Gospel Foundations

"The Thrill Is Gone" (B.B. King, 1969) — Written in 1951 by West Coast blues musicians Roy Hawkins and Rick Darnell. A definitive blues standard recorded by King in late 1969 featuring a lush classical string arrangement.
"Death Letter Blues" (Son House, 1967) — A solo acoustic Delta blues masterpiece recorded in Copenhagen on Oct 11, 1967. Known for House's highly emotional singing and slide guitar playing.
"Grinnin' In Your Face" (Son House, 1965) — A raw Delta blues performance featuring only vocals and handclaps. Known as Jack White's favorite song of all time.
"Didn't It Rain" (Sister Rosetta Tharpe, 1964) — Celebrated live gospel-blues opening song performed in the rain at a disused train station in Manchester in 1964. Originally cut by Tharpe in 1947.

Folk, Rock, and Modern Anthems

"Hurricane" (Bob Dylan, 1976) — Leading catalog track on YouTube, drawing immense traffic from search interest in true crime, cinematic narratives, and civil rights. Written about boxer Rubin Carter.
"Like a Rolling Stone" (Bob Dylan, 1965) — Landmark electric rock track with over 64 million views.
"Subterranean Homesick Blues" (Bob Dylan, 1965) — Famous early music video where Dylan flips cue cards, parodied extensively including by "Weird Al" Yankovic.
"Blind Willie McTell" (Bob Dylan, 1983) — Unreleased outtake from the 1983 Infidels sessions. Tucked away in Bootleg Series Vol. 3. Features Dylan on piano and Mark Knopfler on acoustic guitar.
"Hurt" (Nine Inch Nails / covered by Johnny Cash): NIN song released in 1994, written by Trent Reznor about personal pain and addiction. Johnny Cash's 2002 acoustic cover became a defining masterpiece of Cash's late-career renaissance, backed by a legendary music video directed by Mark Romanek.
"Something in the Orange" (Zach Bryan, 2022): depiction of raw heartbreak under orange skies. High organic streaming metrics on digital platforms.

🎧 Since we have some of the most iconic songs in music history compiled here, I can create an Audio Overview podcast episode to discuss the fascinating stories behind the writing of Hank Williams' "Your Cheatin' Heart" and Patsy Cline's "Crazy."