Special Report

Most Popular Country Songs of All Time

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20. “The First Cut Is The Deepest”
> Artist: Sheryl Crow
> Year song peaked: 2004
> Peak position on Hot 100: 14
> Total weeks on Hot 100: 36

This ballad was written by English folk-pop singer Cat Stevens and recorded by him in 1967. Of the more than 50 cover versions released subsequently, the most famous was Rod Stewart’s 1976 interpretation. That is, until one-time Stewart backup singer Sheryl Crow recorded this country-accented version in 2003.

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19. “Picture”
> Artist: Kid Rock Featuring Sheryl Crow
> Year song peaked: 2003
> Peak position on Hot 100: 4
> Total weeks on Hot 100: 34

Kid Rock – born Robert James Ritchie – recorded heavy metal and underground rap before turning toward his rock-edged brand of country. This song, co-written by Rock and Crow, was originally released as a duet by the two singers. Then, due to contract issues between their respective record labels, Rock re-recorded it with alt-country singer Allison Moorer – and the song entered the Billboard Hot 100 credited to “Kid Rock featuring Allison Moorer or Sheryl Crow” because radio stations played both versions. Crow’s recording charted highest.

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18. “Wanted”
> Artist: Hunter Hayes
> Year song peaked: 2012
> Peak position on Hot 100: 16
> Total weeks on Hot 100: 46

Born into a musically inclined family in Louisiana Cajun country, Hunter Hayes released his first album at the age of nine, and by the time he was 19, he had become a star – opening for Taylor Swift and scoring a No. 1 hit on the country charts with “Wanted.” The single surged into the Billboard Hot 100, reaching No. 13.

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17. “North To Alaska”
> Artist: Johnny Horton
> Year song peaked: 1960
> Peak position on Hot 100: 4
> Total weeks on Hot 100: 23

Honky-tonk singer Johnny Horton recorded this stirring song for the soundtrack of the 1960 John Wayne starrer of the same name. Shortly after it hit the Top 10, Horton was tragically killed in a car accident driving home from a concert.

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16. “Teardrops On My Guitar”
> Artist: Taylor Swift
> Year song peaked: 2008
> Peak position on Hot 100: 13
> Total weeks on Hot 100: 48

The second single released from Swift’s self-titled 2006 debut album “Teardrops” was subsequently added to her second studio album, 2008’s “Fearless.” This iteration became Swift’s first entry onto Billboard’s Hot 100 charts, and the single was certified triple platinum.