#20. 'Check Yes Or No' by George Strait
- Artist: George Strait
- Billboard rank: #20
This playful song is an ode to a lover, whose relationship with the narrator started when they were just kids. The single hit #1 on the country charts in United States and Canada.
#19. 'It's Your Love' by Tim McGraw with Faith Hill
- Artist: Tim McGraw with Faith Hill
- Billboard rank: #19
This collaboration between one of the most famous couples in country music is not their only duet, but it was the most successful. The 1997 song spent six weeks at the top of the country charts and became both musicians' first top 10 hit on the Billboard Hot 100.
#18. 'My Hang-Up Is You' by Freddie Hart
- Artist: Freddie Hart
- Billboard rank: #18
“My Hang-Up Is You” was Freddie Hart’s second #1 hit on the country charts, remaining at the top for six consecutive weeks. The song's narrator admits that his greatest weakness in life is the person he loves.
#17. '19 Somethin'' by Mark Wills
- Artist: Mark Wills
- Billboard rank: #17
Mark Willis’ musical ode to each decade of the late 20th century spent six weeks at #1 on the country charts and peaked at #23 on the Hot 100.
#16. 'Luckenbach, Texas (Back To The Basics Of Love)' by Waylon Jennings
- Artist: Waylon Jennings
- Billboard rank: #16
This 1977 song about a couple who returns to country living after high society takes its toll on their relationship made waves on both pop and country charts.
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#15. 'Live Like You Were Dying' by Tim McGraw
- Artist: Tim McGraw
- Billboard rank: #15
Tim McGraw’s 2004 hit is an ode to loved ones struggling with cancer. It won several major awards, including Single of the Year and Song of the Year at the CMAs, and Best Country Song at the Grammys.
#14. 'Need You Now' by Lady Antebellum
- Artist: Lady Antebellum
- Billboard rank: #14
The 2009 song, about an on-again, off-again relationship, won four Grammy Awards in 2011, including Song of the Year and Record of the Year. In 2011, "Need You Now" became the most downloaded country song, surpassing Taylor Swift’s "Love Story."
#13. 'Once A Day' by Connie Smith
- Artist: Connie Smith
- Billboard rank: #13
“Once A Day” spent eight weeks at the top of the country charts in 1964, setting the record for the most weeks spent at #1 by a female country artist. It was surpassed by Taylor Swift’s “We Are Never Getting Back Together.”
#12. 'Just To See You Smile' by Tim McGraw
- Artist: Tim McGraw
- Billboard rank: #12
McGraw's 1997 single spent 42 weeks on the Billboard country chart, setting the record for the longest run of all time. The song's narrator pledges he will do anything to make his loved one smile.
#11. 'Kiss An Angel Good Mornin'' by Charley Pride
- Artist: Charley Pride
- Billboard rank: #11
This song was Pride’s eighth to top the country charts, and it spent four months on the pop chart. It follows a man's unconditional love for the woman he wakes up to.
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