Kris Kristofferson has made headlines twice in recent weeks, leading fans to wonder about his overall health and well-being as he nears 90.

The 87-year-old songwriting legend was part of Willie Nelson's 90th birthday celebration last April (highlights aired on CBS in December). One month prior, Nelson was inducted into the Rock and Roll Hall of Fame, where he said this:

"Now that Johnny (Cash) and I have been inducted, I wanna give a plug for Waylon (Jennings) — who played with Buddy Holly — and Kris — who sang so many hits — to be inducted too."

Those four men (Nelson, Cash, Jennings, Kristofferson) formed the Highwaymen in the 1980s. The country group released relatively little music compared to their solo canons, but are still appreciated as iconic.

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Kristofferson has made several public appearances in recent years, most frequently at Country Music Hall of Fame medallion ceremonies and almost always on the arm of another legend, like he was with Rosanne Cash at Nelson's birthday bash. Officially, he retired during the COVID-19 pandemic, but that decision wasn't because anything was wrong with him.

"He's really healthy and in good shape," his manager told Variety in 2021.

Echoes of his Alzheimer's misdiagnosis may paint how fans see him. Just a few months after an 2016 all-star celebration of his songs in Nashville, a feature in Closer revealed that doctors had been treating him for the wrong thing for most of a decade.

What Has Happened to Kris Kristofferson?

The "Sunday Morning Comin' Down" writer had been suffering from memory loss since 2009, so his medical team told him it was either Alzheimer's disease, or dementia brought on by being hit in the head so much playing football and boxing when he was younger (similar to the CTE football players often suffer).

In early 2016, a new doctor tested him for something else that can cause memory loss and neurological problems: Lyme disease. The test came back positive, he kicked all of his old medication and spent several weeks treating the right illness and emerged a new man.

"It’s like Lazarus coming out of the grave and being born again," a friend and songwriter named Chris Gantry told the magazine. Another said he was as sharp as he's been in 20 years.

Kristofferson has given very few, if any, interviews in the last five years, and his team hasn't shared anything new about his health. It remains possible that he's suffering from some ailment, but the extent to which he's maligned more than a typical 87-year-old is unknown. Watching him sing with Cash at the Hollywood Bowl was heartwarming. He smiled as the crowd applauded and gave a heartfelt salute. One hopes many more moments like that are in store for the future.

50 Classic Country Artists Today’s Fans Should Know

Today's country music stars owe a debt of gratitude to the legends who formed and cultivated the genre, starting in the early 20th century. These 50 classic country artists remain relevant today. Some developed a style that's emulated on today's country radio. Others set a bar for vocal talent or songwriting skill.

This list of 50 influential classic country artists features country music singers who started their careers before 1990. It's ranked by each artist's current influence on the country music format today, not individual, lifelong impact. Tell us where we got it right or wrong on Twitter.

Gallery Credit: Billy Dukes