In the liner notes of John Prine’s 1971 self-titled debut, Kris Kristofferson -- who discovered Prine while the now-folk icon was making a name for himself in Chicago -- aptly describes Prine as "twenty-four years old and writes like he's two-hundred and twenty."

With a knack for evoking raw emotion, Prine was a lyricist beloved for his stirring authenticity. His songwriting employed empathy in remarkable ways, allowing him to embody characters and tell stories outside of his own perspective, and to produce a catalog with so many different facets that it's hard to believe he hadn't lived a few lives before this one.

In the nearly 50 years since his first record, Prine recorded 18 studio albums and produced a body of work that inspired multiple generations of songwriters. A two-time Grammy winner and a Nashville Songwriters Hall of Fame inductee, Prine was recently announced as one of seven 2020 Grammy Lifetime Achievement Award honorees, and was one of the best and most influential songwriters of a generation.

Prine could count legends such as Johnny Cash and Bob Dylan amongst his biggest fans. He also gave a leg up to contemporary artists including Amanda Shires, Sturgill Simpson, Jason Isbell, Kacey Musgraves and Margo Price, each of whom opened for him on past tours.

With fans and friends across so many genres, news of Prine’s COVID-19-related hospitalization on March 26 sent shockwaves through the music world. Prine died on Tuesday (April 7) from complications from the coronavirus, leaving a gaping hole in the music world that can never be filled.

Taste of Country is taking a look at some of his best tracks. Prepare yourself for some truly incredible storytelling.

  • "Hello in There" (1971)

    If you want a heart-wrenching start, jump in with this one. Born of Prine's lifelong affinity and reverence for the elderly and a childhood memory of delivering papers at an old folks’ home, "Hello in There" has created many an instant fan for Prine, and for Joan Baez, who covered it for her 1975 album Diamonds and Rust. Kris Kristofferson and Bette Midler have also recorded versions of the song.

  • "Pretty Good" (1971)

    This track may not pack the emotional punch of some of Prine’s classics, but there's something to be said for the bluesy rock vocals and guitar work that capture the essence of the time and once captivated a young, emerging guitarist: Sturgill Simpson, who marks "Pretty Good" as his favorite Prine song. It’s no surprise; the track would fit in well on one of Simpson's records, too.

  • "Lake Marie" (1995)

    This track from Prine’s mid-'90s album Lost Dogs + Mixed Blessings has confounded many listeners with the hard left turn it takes in its final verse. "Lake Marie" begins with the story of Native Americans finding two white babies on the shore of the titular lake, goes on to discuss a last-ditch effort to save a marriage as it falls apart, and ends abruptly with images of a grisly crime, leaving listeners to draw their own conclusions. None other than Bob Dylan names this song his favorite of Prine’s.

  • "Angel From Montgomery" (1971)

    Fans may better know Bonnie Raitt’s haunting 1974 cover of this Prine original; though it’s been performed by many artists, from Carly Simon and Tanya Tucker to Brandi Carlile and Maren Morris, Raitt’s version is the most memorable. It's fitting that so many female artists have been drawn to sing "Angel From Montgomery": It began as an idea Prine had to write from the viewpoint of a middle-aged woman who feels older than she is.

    Of his motivation to embody other characters when writing, Prine once said in an interview with Roger Ebert, "In my songs, I try to look through someone else’s eyes, and I want to give the audience a feeling more than a message."

  • "Paradise" (1971)

    "Paradise" tells the story of the ruinous impact of strip mining coal on the bucolic Kentucky mountain community in which Prine's parents grew up. Prine wrote it for his father, but it has resonated for many, becoming a bluegrass standard covered by the likes of John Denver, Dwight Yoakam, Pat Green and Jimmy Buffett.

  • "That’s the Way That the World Goes ‘Round" (1978)

    If you don’t know Prine’s original version of this song from his critically acclaimed Bruised Orange album, you might remember Miranda Lambert’s rocked-up cover from 2009's Revolution. The simple and truthful lyrics of "That's the Way That the World Goes Round" have also made an impact on the songwriting style of Kacey Musgraves, who counts the tune as one of her favorites.

  • "Your Flag Decal Won’t Get You Into Heaven Anymore” (1971)

    "Your Flag Decal Won't Get You Into Heaven Anymore" pulls no punches. The provocative, anti-war statement has divided audiences since Prine first began performing it for crowds early in his career: Though some folks would walk out, others would cheer loudly. It’s a timeless song that continues to resonate because of all the wars suffered since its writing, and it paved the way for bold musical statements from acts such as the Dixie Chicks and Jason Isbell. Brandi Carlile considers this one her favorite Prine song because “it’s been an anthem for the downtrodden and the people in the fringes.”

  • "I Just Want to Dance With You" (1986)

    This simple, sincere number from Prine’s German Afternoons album expresses a most basic desire in the purest way, and proves to be universally relatable. For 1998's One Step at a TimeGeorge Strait recorded his own version many years after Prine’s original cut, his endearing baritone matching its tone perfectly. The single became Strait’s 34th No. 1 single on the Billboard Hot Country Singles & Tracks chart.

  • "In Spite of Ourselves" (1999)

    This album title cut is a catchy duet with Iris Dement, and the only original song on a record otherwise comprised of country classics sung with vocalists such as Trisha Yearwood and Patty Loveless. A little goofy and undoubtedly country, it fits well even though Prine wrote it for Daddy and Them, a comedy film directed by Billy Bob Thornton in which Prine also plays a role.

  • "When I Get to Heaven" (2018)

    When choosing a more recent song from Prine's body of work for this, it’s tempting to go with "Lonesome Friends of Science," a clever song that pities the planet formerly known as Pluto. However, “When I Get to Heaven” -- from the same album, The Tree of Forgiveness -- is the winner.

    Part spoken word, part family sing-along, this song imagines Prine in the afterlife smoking “a cigarette that’s nine miles long” and partaking in all the joys his illnesses of late have forced him to forego. Equal parts silly fun and authentically affecting, it’s a classic example of Prine’s songwriting strengths and time-bending ability to see well beyond his years.

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