#90. 'Killin' Time' by Clint Black
- Artist: Clint Black
- Billboard rank: #90
In 1989, Billboard declared “Killin’ Time” the #2 country song of the year—defeated only by another Clint Black song. Throughout the recording, the narrator complains that he’s wasting his life away drinking in hopes of forgetting a former lover.
#89. 'Girl Crush' by Little Big Town
- Artist: Little Big Town
- Billboard rank: #89
This 2014 hit left critics and audiences confused. What is this song about: having a crush on a woman, or a desire to take over her life to win back the man she stole? The emotionally charged recording hit #1 on the country charts.
#88. 'Our Song' by Taylor Swift
- Artist: Taylor Swift
- Billboard rank: #88
The pop princess’ first massive hit was “Our Song,” which was originally written to be performed at a high school talent show. The artist’s musings about a relationship without a song became a universal hit in 2007, spending 36 weeks on the Billboard Hot 100.
#87. 'Just Got Started Lovin' You' by James Otto
- Artist: James Otto
- Billboard rank: #87
James Otto’s deep vocals have been compared to those of country legend Conway Twitty. His voice was so highly regarded that songwriter Jim Femino personally arranged a meeting to get him in the studio.
#86. 'Pickup Man' by Joe Diffie
- Artist: Joe Diffie
- Billboard rank: #86
In his 1994 ballad, Joe Diffie jokes throughout the course of the song he'll win over the girl of his dreams by driving a pickup truck. The jovial song resonated with audiences and became his longest-lasting #1 hit on the Billboard country charts.
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#85. 'I Fall To Pieces' by Patsy Cline and Jim Reeves
- Artist: Patsy Cline and Jim Reeves
- Billboard rank: #85
This 1961 single is a country standard. Radio stations ignored the song altogether at first, but Patsy Cline’s hit crossed over to the pop charts and hit #1.
#84. '(I'm So) Afraid Of Losing You Again' by Charley Pride
- Artist: Charley Pride
- Billboard rank: #84
Charley Pride had several hits in his day. In this song, the narrator expresses his fear of losing the love of his life.
#83. 'Baby, Baby (I Know You're A Lady)' by David Houston
- Artist: David Houston
- Billboard rank: #83
This 1969 song was the first hit by up-and-coming songwriter Norro Wilson, who went on to write songs for dozens of country music’s most prolific chart-toppers. In this recording, the narrator begs a woman to let him declare his love for her.
#82. 'Lost In The Fifties Tonight (In The Still Of The Night)' by Ronnie Milsap
- Artist: Ronnie Milsap
- Billboard rank: #82
The 1985 single blends a new recording with a cover of the 1956 hit, "In the Still of the Night.” It was Milsap’s 42nd single, 27th #1 hit on the country charts, and first Grammy-winning recording.
#81. 'My Heart Skips A Beat' by Buck Owens
- Artist: Buck Owens
- Billboard rank: #81
“My Heart Skips A Beat” was Buck Owens’ third #1 country hit during a long reign over the charts. The tune is one of several on this list that takes an upbeat approach to relationships.
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