#30. 'All The Time' by Jack Greene
- Artist: Jack Greene
- Billboard rank: #30
Jack Greene covered Kitty Wells' 1959 song in 1967, shooting to #1 on the country charts. The simple song tells a familiar tale of undying love.
#29. 'I've Come To Expect It From You' by George Strait
- Artist: George Strait
- Billboard rank: #29
George Strait’s single hit #1 in 1990, and remained in the top spot for five weeks. The song's narrator expresses unhappiness with a lover who's left him.
#28. 'Heartaches By The Number' by Ray Price
- Artist: Ray Price
- Billboard rank: #28
This 1959 song was so popular that even its sheet music was a best-seller. More than a dozen artists have released covers of "Heartaches By The Number" over the years, several of which appeared on the country charts. The song lists all the times a lover has broken the narrator's heart.
#27. 'Don't Let Our Love Start Slippin' Away' by Vince Gill
- Artist: Vince Gill
- Billboard rank: #27
Vince Gill, who boasts the record for most consecutive years hosting the CMAs (a whopping 12 times), released this single in 1992 at the start of his reign over country music. The song peaked at #1 on the country charts.
#26. 'Have Mercy' by The Judds
- Artist: The Judds
- Billboard rank: #26
The Judds' third song on the list of best country songs is yet another condemnation of a man who treats a woman poorly. The 1985 single spent 14 weeks on the country charts.
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#25. 'Chattahoochee' by Alan Jackson
- Artist: Alan Jackson
- Billboard rank: #25
This fast-paced, heartfelt song filled country music fans with hopeful nostalgia. The 1993 song received CMA awards for Single of the Year and Song of the Year.
#24. 'If You're Going Through Hell (Before The Devil Even Knows)' by Rodney Atkins
- Artist: Rodney Atkins
- Billboard rank: #24
Rodney Atkins’ upbeat anthem spent four weeks at the top of the country charts in 2005 before breaking into the Billboard Hot 100. The lyrics encourage listeners to keep on fighting when the going gets tough.
#23. 'Here You Come Again' by Dolly Parton
- Artist: Dolly Parton
- Billboard rank: #23
Dolly Parton’s first big pop crossover hit topped the country charts for five weeks and earned her a Grammy for Best Female Country Vocal Performance. Parton’s song, in which she sings about a man she just can’t seem to get over, has been covered more than a dozen times.
#22. 'How Do You Like Me Now?!' by Toby Keith
- Artist: Toby Keith
- Billboard rank: #22
Toby Keith sings to a girl who once rejected him, flaunting his newfound fame in this 1999 honky-tonk jam. The song earned several award nominations, and hit the top of the country chart, breaking into the Top 40 as well.
#21. 'Rhinestone Cowboy' by Glen Campbell
- Artist: Glen Campbell
- Billboard rank: #21
Country music legend Glen Campbell’s hit “Rhinestone Cowboy” resonated with any country music fan who ever dreamed of becoming a star. The 1975 hit has been covered by artists like Blake Shelton and Tim McGraw.
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