Special Report

Country Musicians With the Most Hits

Charles Stockdale, John Harrington

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37. Ronnie Milsap
> Total songs on Hot Country Songs chart: 55
> Longest-charting hit: A Woman In Love (25 weeks)

Ronnie Milsap, who was born nearly blind due to congenital glaucoma, developed an affinity for music at an early age, playing various instruments before picking up the piano. Milsap, who was influenced by R&B and rock and roll, charted on Billboard’s R&B Songs list in 1965 with “Never Had It So Good,” co-written by Nickolas Ashford and Valerie Simpson. Milsap was a fixture on the Billboard Hot Country Songs chart with 35 No. 1 songs. He posted his first two in 1974 — “Pure Love” and “Please Don’t Tell Me How the Story Ends” — and his latest two chart-toppers — “Don’t You Ever Get Tired (Of Hurting Me)” and “A Woman In Love” — in 1989.

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36. Jim Reeves
> Total songs on Hot Country Songs chart: 56
> Longest-charting hit: He’ll Have To Go (34 weeks)

Country crooner “Gentleman” Jim Reeves from Galloway, Texas, had one of country’s biggest crossover hits with “He’ll Have To Go,” which reached No. 2 on the Billboard Hot 100 in 1960. He authored eight No. 1 hits on the Hot Country Songs chart, singing with his rich mellow baritone voice. “I Guess I’m Crazy,” “Billy Bayou,” and “This Is It” were among his hits. Such was his popularity that six of Reeves’ No.1 hits topped the country chart after his death in an airplane crash in 1964.

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35. Brooks & Dunn
> Total songs on Hot Country Songs chart: 57
> Longest-charting hit: Only In America (32 weeks)

The duo of Kix Brooks and Ronnie Dunn have sent a total of 57 songs to the Hot Country Songs chart since the early 1990s, with 20 singles hitting No. 1. Among these hits are country radio classics such as “Red Dirt Road,” “Brand New Man,” and “Neon Moon.” Numerous songs from their recent “Reboot” album — which features classic songs performed with newer country musicians — have charted over the past year, including collaborations with Luke Combs, Kacey Musgraves, and Kane Brown.

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34. Charley Pride
> Total songs on Hot Country Songs chart: 59
> Longest-charting hit: Kiss An Angel Good Mornin’ (18 weeks)

Baritone-voiced country singer Charley Pride embarked on his solo music career in 1958, recording a demo at the famous Sun Studio in Memphis. It was not until 1966 that he signed to RCA Records, however, and saw his career begin to take off. Over the following decades, Pride would release 52 Top 10 hits, 29 of which topped the Hot Country Songs chart. Among his No. 1 songs are “Night Games,” “Mountain of Love,” and “Kiss An Angel Good Mornin’.” Pride is the most successful black country singer of all time.

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33. Bobby Bare
> Total songs on Hot Country Songs chart: 59
> Longest-charting hit: The Streets Of Baltimore (20 weeks)

The country singer-songwriter from Ironton, Ohio, weathered adversity in his youth to create a durable career. Bobby Bare shifted from country to folk to pop and back to country. He was influenced by Bob Dylan and recorded music in England with Liverpool country acts. “Detroit City” was his highest charting single on the Billboard Hot 100, reaching No. 16 in August 1963. Bare had 13 Top 10 hits on the Billboard Hot Country Songs chart, with “Marie Laveau” his lone No. 1 in July of 1974.

Bare, who was respected by musicians in various genres, continued to record into the 21st century.