On This Day Over 3 Decades Ago, a Country Legend Scored His 40th—and Final—No. 1 Hit

Ronnie Milsap’s chart run is the kind of achievement that sounds exaggerated until you say it out loud: 40 No. 1 hits.

And on this day more than three decades ago, the Country Music Hall of Famer reached that milestone with what would also become his final trip to the top of Billboard’s Hot Country Singles chart, putting Milsap in rarified air among the genre’s most dominant hitmakers.

The song was “A Woman in Love,” and it appeared on an album with a title that feels especially timely right now: Stranger Things Have Happened. Released in 1989, the project produced multiple major singles and remains one of the late-career highlights in Milsap’s catalog.

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And yes, if that album title suddenly looks familiar on your screen: Netflix’s Stranger Things is in the middle of its final-season rollout, with new episodes arriving on Christmas Day and the series finale set for New Year’s Eve, making the phrase a particularly hot search topic this week.

Milsap’s 40 No. 1s are a reminder of just how long he stayed not only relevant, but unavoidable on country radio. His career spans multiple eras of the genre, from the smoother, crossover-friendly ’70s and ’80s sound to a landscape that began shifting hard as the ’90s approached. To rack up 40 chart-toppers in the middle of that kind of change is exactly why Milsap’s name gets mentioned in the same breath as other country heavyweights like George Straitand Conway Twitty. They are the only country artists to have charted 40 No. 1 hits.

What’s striking about Milsap is that he was born almost completely blind and in his teenage years lost what little sight he had left. Yet he became a classically-trained musician, learning several instruments and becoming particularly outstanding on the piano, which is what he became known for when he started getting famous.

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What’s also striking is that the 82-year-old Milsap isn’t frozen in amber. Even now, he still pops up in fan-facing spaces, including his YouTube interview series Music and Millsap, where he sits down with fellow country artists to talk craft, the road, and the business. In a 2025 episode with Larry Gatlin, Milsap opens with, “Hello, everybody. This is Ronnie Millsap, back for another podcast, Music and Millsap, episode number 44.”

He also sounds exactly like a veteran artist who’s adapted to modern listening habits without losing his old-school instincts: “I got good wi-fi, and I got Alexa, that thing’s an amazing tool.”

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That through-line, the craft, the work, the staying power, is what makes the 40th No. 1 milestone hit a little harder. Chart records can feel like trivia until you remember they’re built on real people choosing to press play, week after week, year after year.

Or, as one listener put it in a note shared on the show: “I just wanted to say thank you for all your wonderful music over the years. I became an adult listening to you. I’m 55 now, and there isn’t a single song that I’ve listened to and can’t relate to. You are by far one of the most profound, talented, good-looking artists I’ve ever listened to. So thank you.”

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