Only 19 Artists Have Topped Billboard’s ‘Hot Country Songs’ Chart Twenty Times

Chart performance doesn't equal music quality, I think we all know that, but there's still something so clean about looking back at a genre through the lens of its biggest songs. For as much as we champion the album, there's no denying that hit singles dominate all music segments, even country music. You'd be hard pressed to find a person who doesn't associate country music with megahits like "Friends In Low Places", "Chicken Fried", or (sigh) "Wagon Wheel" and instead immediately thinks of Keith Whitley's Don't Close Your Eyes or Dolly Parton's Coat Of Many Colors. Maybe next I'll dig into the artists with the best album chart performance but for today, let's take a look at every single country artist that secured 20 or more number ones on Billboard's Hot Country Songs chart. Where available, these numbers have been pulled directly from Billboard's artist pages ( here's George Strait's for reference) so they may go against some figures you've seen reported elsewhere which may include Country Airplay, Adult Contemporary, or Hot 100 tracks. To keep this list consistent, I decided to only use what's shown directly on Billboard's website, at least where it's available. You'll see in the list there's some artists whose pages aren't working for some reason, in which case I had to use other sources, which will be linked. Here's a list of all 19 country artists who secured 20 or more number ones on Billboard's Hot Country Songs chart:

George Strait - 44

• First - "Fool Hearted Memory" (1982 - Strait from the Heart)
• Latest - "River Of Love" (2008 - Troubadour)
• My Favorite - "You Look So Good In Love" (1983 - Right or Wrong)

Conway Twitty - 40

• First - "It's Only Make Believe" (1958 - Sings )
• Latest - "Desperado Love" (1986 - Fallin' for You for Years)
• My Favorite - "Tight Fittin' Jeans" (1981 - Redneckin' Love Makin' Night )

https://www.youtube.com/watch?v=fEr3nqEFuDA

Merle Haggard - 38

• First - "I'm a Lonesome Fugitive" (1966 - I'm a Lonesome Fugitive)
• Latest - "Twinkle, Twinkle Lucky Star" (1987 - Chill Factor)
• My Favorite - "Sing Me Back Home" (1967 - Sing Me Back Home )

Ronnie Milsap - 35?

This is where Billboard's website first fails us... For some reason Ronnie Milsap's page doesn't exist ( check it for yourself) so I had to go to other sources. His website says he had 35 and that number can be found elsewhere so we'll go for it here. The fact he doesn't have an artist page on Billboard is yet more proof that this man deserves some credit .

• First - "Pure Love" (1974 - Pure Love )
• Latest - "A Woman In Love" (1989 - Stranger Things Have Happened )
• My Favorite - "(There's) No Gettin' Over Me" (1981 - There's No Gettin' Over Me )

https://www.youtube.com/watch?v=oXe5ETmifkM

Alabama - 33

• First - "Tennessee River" (1980 - My Home's In Alabama )
• Latest - "Reckless" (1993 - Cheap Seats )
• My Favorite - "I'm In A Hurry (And Don't Know Why)" (1992 - American Pride )

Charley Pride - 29

• First - "All I Have to Offer You (Is Me)" (1969 - The Best Of Charley Pride )
• Latest - "Night Games" (1983 - Night Games )
• My Favorite - "Kiss An Angel Good Mornin'" (1971 - Charley Pride Sings Heart Songs )

Eddy Arnold - 28?

Another failure of Billboard's website. Apparently they don't add singles from old, comparable charts from before the 60's, which is when Arnold was at his peak. FoxNews and Discogs both reference 28 number one's, so for this list we'll go with it, though I think their may be some inclusions from other charts in that figure.

• First - "What Is Life Without Love?" (1946 - Single)
• Latest - "Then You Can Tell Me Goodbye" (1968 - Walkin' In Love Land )
• My Favorite - "The Cattle Call" (1955 - The Cattle Call )

Tim McGraw - 26

• First - "Don't Take The Girl" (1994 - Not A Moment Too Soon )
• Latest - "Humble and Kind" (2016 - Damn Country Music )
• My Favorite - "Felt Good On My Lips" (2010 - Number One Hits )

Alan Jackson - 26

• First - "I'd Love You All Over Again" (1990 - Here in the Real World )
• Latest - "Country Boy" (2008 - Good Time )
• My Favorite - "Drive (For Daddy Gene)" (2002 - Drive )

Dolly Parton - 25

• First - "Joshua" (1970 - Joshua )
• Latest - "Rockin' Years" (1991 - Eagle When She Flies )
• My Favorite - "Jolene" (1973 - Jolene )

https://www.youtube.com/watch?v=Ixrje2rXLMA

Reba - 24

• First - "Can't Even Get the Blues" (1982 - Unlimited )
• Latest - "Turn On the Radio" (2010 - All the Women I Am )
• My Favorite - "Whoever's in New England" (1986 - Whoever's in New England )

Kenny Chesney - 23

• First - "She's Got It All" (1997 - I Will Stand )
• Latest - "Setting the World On Fire" (2016 - Cosmic Hallelujah )
• My Favorite - "The Good Stuff" (2002 - No Shoes, No Shirt, No Problems )

Sonny James - 21

• First - "Young Love" (1956 - The Sonny Side )
• Latest - "Is It Wrong (For Loving You)" (1974 - Is It Wrong )
• My Favorite - "Young Love" (1956 - The Sonny Side )

Kenny Rogers - 21

• First - "Lucille" (1977 - Kenny Rogers )
• Latest - "Buy Me a Rose" (1999 - She Rides Wild Horses )
• My Favorite - "Coward of the County" (1979 - Kenny )

Buck Owens - 21

• First - "Act Naturally" (1960 - The Best of Buck Owens )
• Latest - "Made In Japan" (1972 - In the Palm of Your Hand )
• My Favorite - "I've Got a Tiger by the Tail" (1964 - I've Got A Tiger By The Tail )

https://www.youtube.com/watch?v=8_c1dkh9YKQ

Willie Nelson - 21

• First - "Blue Eyes Crying in the Rain" (1975 - Red Headed Stranger )
• Latest - "Nothing I Can Do About It Now" (1989 - A Horse Called Music )
• My Favorite - "My Heroes Have Always Been Cowboys" (1980 - The Electric Horseman )

Tammy Wynette - 20

• First - "My Elusive Dreams" (1967 - My Elusive Dreams )
• Latest - "You and Me" (1976 - You and Me )
• My Favorite - "D-I-V-O-R-C-E" (1968 - D-I-V-O-R-C-E )

https://www.youtube.com/watch?v=912DKxD0H1U

Brooks & Dunn - 20

• First - "Brand New Man" (1991 - Brand New Man )
• Latest - "Play Something Country" (2005 - Hillbilly Deluxe )
• My Favorite - "My Maria" (1996 - Borderline )

Toby Keith - 20

• First - "Should've Been a Cowboy" (1993 - Toby Keith )
• Latest - "Made In America" (2011 - Clancy's Tavern )
• My Favorite - "She Never Cried In Front Of Me" (2008 - That Don't Make Me a Bad Guy )

https://www.youtube.com/watch?v=rD1E9qj7e8s