100 Best Country Songs of All-Time: Part Four (39–20)

Two parts to go!

39.) “Lovin’ Her Was Easier (Than Anything I’ll Ever Do Again)”
Artist: Kris Kristofferson
Writer: Kris Kristofferson

The lyrics are pure poetry, with vivid allusions and poignant, specific memories. The songwriting master at work.

38.) “Seminole Wind”
Artist: John Anderson
Writer: John Anderson

Country music has a proud tradition of pro-environmental songs, and “Seminole Wind” is the best of the bunch, strongly decrying the destruction of the Everglades.

37.) “City Lights”
Artist: Ray Price
Writer: Bill Anderson

Bill Anderson is one of pure country music’s greatest songwriters. This simple song about loneliness helped launch Whisperin’ Bill’s legendary career.

36.) “Golden Ring”
Artists: George Jones and Tammy Wynette
Writers: Bobby Braddock and Rafe VanHoy

Such clever songwriting. This well-known duet from the two country icons traces a pawn-shop ring through being sold, marriage, and divorce.

35.) “The Ride”
Artist: David Allan Coe
Writers: Gary Gentry and J.B. Detterline Jr.

A spooky, spooky song. Try listening to it without getting goosebumps. The best part about the song? It’s such a believable account.

34.) “Delta Dawn”
Artist: Tanya Tucker
Writers: Larry Collins and Alexander Harvey

“Delta Dawn” was Tanya’s first hit and established her as artist much more mature than her age.

33.) “The Gambler”
Artist: Kenny Rogers
Writer: Don Schlitz

“The Gambler” has become a country standard. Country Music Hall of Famer Don Schlitz wrote a set of brilliant, life-lesson lyrics, and Kenny Rogers interpreted it in masterful fashion.

32.) “I’ve Been Everywhere”
Artist: Hank Snow
Writer: Geoff Mack

There must be few songs that have been covered more than this one. The spitfire listing of popular cities and places across North America made “I’ve Been Everywhere” more than just a novelty song.

31.) “Honky Tonk Heroes”
Artist: Waylon Jennings
Writer: Billy Joe Shaver

If I could pick one song to send 500 years into the future to explain outlaw country, I’d go ahead and pick “Honky Tonk Heroes.”

30.) “Silver Wings”
Artist: Merle Haggard
Writer: Merle Haggard

“Silver Wings” has a song structure that would get laughed out of a modern-day songwriting session. But Merle didn’t care about norms and sure as hell never did what was expected. It’s a beautiful piece of writing.

29.) “Would You Lay With Me (In a Field of Stone)”
Artist: Tanya Tucker
Writer: David Allan Coe

Tanya would be no stranger to controversy during her legendary career, and her recording of the mature lyrics here caused some to look down their noses at her. But guess what? Tanya has always done what she wanted and always will. This was more than a typical love song, with lyrics from Coe that rose above the usual themes.

28.) “The Window Up Above”
Artist: George Jones
Writer: George Jones

George said himself that it was his best record, and though you could point to a great many other Jones records as competition, who am I to argue with The Possum? “The Window Up Above” is one of many in a long line of recordings from George that seemed ripped from the pages of his own life.

27.) “Ring of Fire”
Artist: Johnny Cash
Writers: June Carter and Merle Kilgore

Mariachi horns, love as a burning fire. It’s an unusual formula for a hit country record, but The Man in Black did things his way.

26.) “The Devil Went Down to Georgia”
Artist: The Charlie Daniels Band
Writers: The Charlie Daniels Band (Including Charlie Daniels and Tom Crain)

A Southern Rock and Country standard, “The Devil Went Down to Georgia” has reached iconic status in the annals of American music history.

25.) “Folsom Prison Blues”
Artist: Johnny Cash
Writer: Johnny Cash

“I hear that train a-coming/it’s rolling ‘round the bend…”

24.) “L.A. Freeway”
Artist: Guy Clark
Writer: Guy Clark

Guy was feeling down and out when he wrote this lonesome, but regret-free look at leaving Los Angeles. Guy was a master who studied every aspect of songwriting.

23.) “Crazy”
Artist: Patsy Cline
Writer: Willie Nelson

“Crazy” defines The Nashville Sound and the historic decade of Nashville records.

22.) “The Grand Tour”
Artist: George Jones
Writers: Norro Wilson, Carmol Taylor, and George Richey

A good case can be made that “The Grand Tour” is the saddest country song of all-time. The last verse will just tear you apart.

21.) “I Walk the Line”
Artist: Johnny Cash
Writer: Johnny Cash

Johnny Cash transcends country and transcends rock ’n’ roll. Much like Waylon, Johnny is a revolutionary figure in the annals of country music. “I Walk the Line” is the perfect example of Johnny’s famous boom-chicka-boom sound.

20.) “Coal Miner’s Daughter”
Artist: Loretta Lynn
Writer: Loretta Lynn

You simply don’t get much more autobiographical than this. Loretta poured out her upbringing in Butcher Hollow right into song.