Freedy Johnston: A Love Letter in 16 Songs

David picks some favorite tracks for the singer-songwriter's 65th birthday

Freedy Johnston first grabbed national attention when his 1992 album, Can You Fly, received rave after rave after rave. Dean of American Rock Critics, Robert Christgau, led the charge. Christgau deemed Can You Fly an “impossible record,” as in “a perfect” one in a Village Voice essay, graded it “A+” in his “Consumer Guide” column and, in Playboy, declared it “the strongest album by a new male singer-songwriter in at least a decade.” I second each of those judgements. From here in 2026, I will even see his “at least a decade” and raise him to at least the last 45 years. Can You Fly remains not only undiminished to me all these years later (which is really saying something for an album that was one of the handful to which my wife and I fell in love)—but more inviting and complicated, more perfect and mysterious, more fun than ever, deepened.

The pride (however belatedly) of little Kinsley, Kansas, singer-songwriter Freedy Johnston emerged with an irresistible backstory: He sold the acres his grandfather left him to finish the album and finance a music career. And make no mistake, the preeminence of Can You Fly aside, he has had a career. He left Kinsley young, moved to college town Lawrence, KS for a time, then headed for New York City—and he’s bounced all over since. Along the way, he’s made way more fantastic music than I can account for here. But as I’ve been listening to Johnston on repeat lately, on the heels of seeing him perform an intimate basement gig in Lawrence, KS last month (at Eighth Street Tap Room; see image at bottom), and as Johnston turned 65 this month (right behind you, myself), I wanted to honor him with an installment of our “A Love Letter in 16 Songs” series. (Why 16? Why not?)

I guess Johnston is most often described, if only generically, as a kind of indie rock (but AOR friendly?) singer-songwriter. The way that tends to work is that the bulk of the critical attention gets paid to his lyric sheets. Johnston writes words you want to study and is a master storyteller. He imagines the lives of typically everyday folks (a category that often coincides in his work with what you might call “losers”—this is a compliment) in concise language, a la Raymond Carver short stories, and his tales can include chilling twists and revelations, a la the best pulp fictions. His style, especially when it comes to his 1990s work, has been quite literate in style, as well, and occasionally, even literary in its allusions. I didn’t include it below, but I recommend his “Dolores,” from Can You Fly follow-up This Perfect World, about a man admitting to himself that he’s edging into Lolita territory (“She’s read the book and everything!”). Can’t prove it but I’ve also always assumed that Can You Fly’s title track was inspired by the Gabriel Garcia Marquez story “A Very Old Man with Enormous Wings.”

So, yes, great words and stories. But I would encourage listeners to focus on the singer half of this singer-songwriter, too: Johnston is a distinctive, moving vocalist and deceptively smart with his phrasing. Most of all, I want to underscore Johnston’s real secret weapon: A knack for hooks that stick and for haunting melodies that render all the words conversational.

What’s below counts as my 16 favorite Freedy Johnston cuts, at least this week. I tried to wave in the direction of covering bases across his career but of course missed a great deal. So far this century, we’ve only been gifted with a new album of Freedy Johnston originals about every seven years or so on average. I hope his next album speeds that schedule. In the meantime, I wanted to say thanks.

1. Freedy Johnston – “Trying to Tell You I Don’t Know” (from Can You Fly, 1992)

Writing great songs can take plenty of time and effort, but it doesn’t cost much. If you want to make your song into a great record, though, you’re going to need some capital. “Trying to Tell You I Don’t Know” is a song about needing money up front to pay your musicians, to book studio time, to pay for gas and meals and motel rooms while on tour. “I sold the dirt to feed the band,” he sings, tweaking that transaction a verse later to “I sold the dirt and bought the road.” “Trying to wake up in your head, trying to cry with the red light on” underscores that Johnston’s end game was to transform the songs he’d written on the cheap into the records he heard in his head. Well, Freedy got what he paid for. Can You Fly is a great sounding record, sonically thrilling well before the songwriting fully registers. Straight out the gate, “Trying to Tell You I Don’t Know” hurtles furiously along thanks to the drumming of Brian Doherty, the snarling lines of guitarist Kevin Salem and the pulsing, melodic bass work of Joe Jackson-sideman Graham Maby (who co-produced the album to boot). “I sold the dirt to feed the band” is the artful, oft-quoted line that begins the song proper. But what kicks off the record, all staticky and lo-fi—like trying to hang on to a dream before its gone or like pulling in a radio station half a country away—is the terrifying moment when Johnston realized the bargain he was prepared to make: “At two o’clock this morning, I was sittin’ up in my bed…” Was selling his land to finish his album the right call? His song is trying to tell us he’s never quite going to know. The record he made out of his song sounds pretty confident.

2. Freedy Johnston – “Tearing Down This Place” (from Can You Fly, 1992)

Freedy’s “Tearing Down This Place” uses a demolition crew leveling an old house as a metaphor for the end of a marriage. As Freedy and crew knock down the old homeplace and haul it off, he imagines the emotional walls and tears it once housed, all the “complicated,” “undecided” nights. Freedy’s song is an expansion of that verse in Lucinda Williams’ “Side of the Road,” where she wonders about folks living in a farmhouse out aways, or maybe of Bruce Springsteen’s “Cautious Man” where a man “with his own hands builds a great house down by the riverside” for his bride. “Tearing Down This Place” is complicated and generous, full of lived-in wisdom. A work song about domestic labor.

3. Freedy Johnston – “The Mortician’s Daughter” (from Can You Fly, 1992)

A perfect song and a perfect example of Johnston’s songwriting chops, starting with the title itself. Opting for “the mortician,” rather than “a mortician,” roots us effortlessly in some anonymous, specific, small town. “Funeral director” would be too many syllables, “undertaker” too creepy and old-timey, but “mortician” grants Freedy’s mournful tale the formality and emotional distance it needs. Throughout the song, life and death abut cruelly: “We drew our hearts on the dusty coffin lids” and “We rolled in the warm grass by the boneyard fence,” “wilted flowers” and “the first leaves falling.” Johnston’s narrator is reading a letter with bad news about a young woman he loved, once upon a time. “My tears dissolve an image from the careful ink”—and instantly his memories, and his now hurtling melody, fling him back “there again,” seeing the mortician’s anger again, hearing the daughter’s whispered “It doesn’t matter.” It’s too much. Johnston moans, wails wordlessly. When he’s gathered himself, he captures the loss, corrals the pain, in an image. “There’s a lonely dove out on the telephone wire,” he sings. “I turn my head and she flies away.” Alt-cellist Jane Scarpantoni bows an elegy to the fade.

4. Freedy Johnston – “Fun Ride” (from The Trouble Tree, 1990)

The Trouble Tree, Johnston’s debut album (named after a Kinsley, KS bar where some no-good commotion or other seemed always to be going down), is a bit of an anomaly in his catalog. A portrait of the man as a young artist. The arrangements here, which soon enough would be layered tight as a drum, sound spare and busy at once, and there are a lot more words involved too, an explosion of them, from a verbal adept who very soon embraced concision. And he’s yet to wrestle his nasal tone and limited range into his one-of-a-kind mature style. When I tracked it down after falling in love with Can You Fly and while waiting for This Perfect World, I found it more interesting than anything, but the one track off the album I never forget was “Fun Ride.” Played out a bit like a one-man, one-act play, Johnston talks us through a day with a man who’s calling in sick because there’s a carnival in town: “Get some clothes on for a change,” he tells his girlfriend. “Cuz we’re leaving in two minutes!” The ride he can’t wait to try takes the couple up and down and up again as Freedy, backed by jerking beats and faintly jazzy guitar solos, flits between commenting on their relationship and thrilling to the ride itself until, in a blur of words, ride and relationship become indistinguishable. “Fun Ride” is fun. And the “best thing’s when you turn around, look back…”

5. Freedy Johnston – “Bad Reputation” (from This Perfect World, 1994)

Goosed by a pair of impossible-not-to-sing-along openers (“I know I’ve got a bad reputation / And it isn’t just talk, talk, talk” and “I couldn’t have one conversation / If it wasn’t for the lies, lies, lies”), this is the Freedy Johnston song even those poor souls still unenlightened about Freedy Johnston are most likely at least to recognize. It was the lead track to his major label debut, it climbed to No. 54 on the Hot 100 in 1995, then it got a second and (and ongoing) bump in popularity a year later when the Farrelly Brothers memorably needle dropped it in Kingpin. Thirty years on, what sticks most for me, though, is the song’s unusually long, lost and beseeching “do-you-want-me-now” chorus—especially its “Suddenly I’m in Herald’s Square, looking in the crowd your face is everywhere,” which strikes me as musical kin to a dozen fantastic Marshall Crenshaw numbers and, thematically, to Crenshaw’s “You Should’ve Been There.” Make that, musical close kin: Crenshaw contributes 12-string to the very next track, “Evie’s Tears” as well as a 6-string bass solo to “Remember Me” on Can You Fly.”

6. Freedy Johnston – “This Perfect World” (from This Perfect World, 1994)

You’ll sometimes find critics complaining that Butch Vig’s pristine production on This Perfect World is a poor match for the kind of material Johnston’s writes. But to my ears it feels like a, uh, perfect fit and likely a deliberate one too. The title track is a case in point. The lyric leaks peril: “You ought to lock that door,” “Last time I was here they found her in the lake,” “No matter what I’ve done...” Johnston provides glimpses of a terrifying, violent narrative and only magnifies the menace by keeping the specifics mysterious. Our horror at whatever the narrator has done wrestles to a draw exquisite tune and its twinkling arrangement, and those contrasts exacerbate our dread even as they draw us closer. The world is not perfect at all, but this record is.

7. Freedy Johnston – “Earn Enough for Us” (from A Testimonial Dinner, 1995)

Though his albums are all but entirely stocked with originals, Johnston has made a point to record covers straight along. Unlucky, his extended-play follow-up to Can You Fly, included an affectingly shaky-yet-committed reading of “Wichita Lineman,” where Freedy climbed to the absolute tip top of his range and then, somehow, climbed just beyond it. He released an all-covers album, My Favorite Waste of Time, in 2007, split between songs by the sorts of rock gods he likely cranked while driving the section roads around Kinsley, KS (Paul McCartney, Tom Petty) and by the power pop contemporaries he discovered after he moved to university town Lawrence and up to NYC (Marshall Crenshaw, Matthew Sweet). Over the years, he’s also covered Edison Lighthouse, Tom T. Hall, Warren Zevon, and, in the all-star let’s-play-the-records-for-fun-and-charity side-project The Know-It-All Boyfriends, Cheap Trick, the Bee Gees and more. My favorite Freedy cover, though, is the version of “Earn Enough for Us” that he contributed to 1995 tribute album, A Testimonial Dinner: The Songs of XTC. I’ve been a big fan of Andy Partridge’s ridiculous knack for herky-jerky beats, elastic vocal attack and sticky melodic hooks since if first heard “Reel by Reel” in college. But in this case, I think Johnston’s cover improves on the band’s original Skylarking track: It strips away the song’s quirky XTC-isms, plays it closer to straight—splits the difference between AOR hero Petty and indie-pop luminaries R.E.M. Johnston’s “Earn Enough for Us” is a sunny, conflicted ode to worry: bills to pay, another mouth to feed, and not even any dirt left to sell.

8. Freedy Johnston – “Western Sky” (from never home, 1997)

Another Raymond Carver-style short-story that emphasizes character over plot. A husband has a fear of flying, so when his wife catches a flight back home, he makes a two-day drive to meet her. They’re soulmates, and this love song is about their temporary separation—and their worries for the other. He’s spelling out her name in neon passing by. She cautions “the road can hypnotize.” When he stops at a motel halfway to spend the night and call home, “she answered before it rang.” The story is set up, ostensibly, from the man’s point of view, but by the end “Glad you’re there, you know my fear” could be each of them talking over the other. What are those unspecified words Freedy says they need to hear from the other before hanging up? Most likely “I love you” or, the same thing, “Be safe.” Johnston’s aching, careful melody yokes them together across the lonely miles.

9. Freedy Johnston – “Gone to See the Fire” (from never home, 1997)

For “Gone to See the Fire,” Johnston drops creepy clues as he goes like someone offhandedly flicking ashes from a cigarette and, like a Jim Thompson novel, the thrill is in figuring out for yourself the eerie depths of the mystery as you go. With that in mind, please be warned that the sentences ahead include SPOILERS: I’m not sure how it would even occur to someone to write a song about a woman discovering that her new boyfriend is a pyromaniac, but this surely must be the very best one of those ever written. “When the roof fell in, he lit up again…”

10. Freedy Johnston – “Moving on a Holiday” (from Blue Days Black Nights, 1999)

The only decorating going on in “Moving on a Holiday” is “the year’s first good snow” falling on a “vacant yard,” the lyric’s only acknowledgement of the season are the traffic signals, “red and green.” No cheer, no loved ones near, just a trunk full of your shit in boxes and a solitary tune echoing in empty rooms. “Old address book in my hand, how’d I lose my place again…” The lonesomest Christmas song you’ve ever heard.

11. Freedy Johnston – “Love Songs about Girls” (from The Way I Were: 4-Track Demos 1986-1992, 2004)

The Way I Were is an album of songs Johnston thought enough of to document for himself but never to record officially, pulled from those tender years leading up to Can You Fly. Early champion Christgau, who loves him some Freedy but hardly all of it, graded The Way I Were an A-, observing that while some cuts would never cut it on a more formal release, they still “achieve a fun his real albums avoid with no sacrifice in ambivalence or bite.” The one I come back to is “Love Songs about Girls.” Johnston’s guitar strum somehow suggests a marimba; his breathless early talk-sing style here is more breathless talk than sing but unaccountably melodic even so. About being stalked through your day by love-songs records on the air, it can double either as a cynical college rocker sick of pop radio’s romantic parade or as another brokenhearted fool whose baby’s gone and won’t leave him alone. Use it for both! Not available for streaming, I’m afraid, but Cantwell Sez it’s worth tracking down.

12. Freedy Johnston – “Don’t Fall in Love with a Lonely Girl” (from Rain in the City, 2010)

If you’ll indulge me as I press this distinction again… I think my favorite Freedy song is “The Mortician’s Daughter” (see above), but I think my favorite Freedy record is “Don’t Fall in Love with a Lonely Girl.” Off 2010’s Rain in the City, his first album of new songs in more than a decade, “Lonely Girl” didn’t sound like anything he’d cut before. That’s mostly down to a staccato-piano beat goosing the choruses and to an enormous string arrangement. He’s warning us off lonely girls, who he says keep silent and to themselves all day before disappearing God knows where all night long—though, key point, such cynical advice has come too late help him say goodbye to the woman he also wishes to marry. “She’s out doing things I can’t imagine,” he gulps, but the anxious rhythm and those edgy, larger-than-life strings suggest his imagination is working just fine. A power-pop “Walkin’ the Floor Over You.”

13. Freedy Johnston – “The Other Side of Love” (from Rain in the City, 2010)

From the dramatic, Phil Specterish guitar-and-drum kick off to the big, earworm chorus, this comes as close to anthemic as any Johnston song I can name. For once, he’s dumped a specific narrative in favor of predicting our universal misery When “you’re all alone, you’ll curse the day you ever were loved or you had a happy home… You’ll walk the streets of a city you used to love…” Freedy wants to know who will bring these brokenhearted souls back from some such dark places. He doesn’t have any answers, and he notably doesn’t volunteer, but maybe his song will help.

14. The Hobart Brothers and Lil’ Sis Hobart – “I Am Sorry” (from At Least We Have Each Other, 2012)

For this delightfully shaggy-dog side project, The Hobart Brothers are Freedy Johnston and the gravel-voiced Austin singer-songwriter Jon Dee Graham and their lil’ sis is Susan Cowsill. It’s a lovely, easy-going album that I recommend. My favorite cut hands down, though, is a Freedy contribution, “I Am Sorry.” It starts with a humbled Freedy singing carefully, fragilely, with Cowsill harmonizing bittersweetly back there behind him somewhere. As we piece the situation together, we learn he’s just stormed out after a fight with his girlfriend, but now that his battery’s gone dead, he wants her to bring him jumper cables and the jacket he left behind to the gas station he’s calling from: “No, not that one. It’s the Citgo by the airport.” Freedy makes each iteration of “I am sorry” sound so pathetic that want to believe he’s sincere. But… Does this poor schlub really want to try to make it work or does he just need a ride? We can’t say for sure. That’s another song.

15. Freedy Johnston – “Baby, Baby Come Home” (from Neon Repairman, 2015)

Such a lovely pop song. One way to hear it is as a gender-flipped version of the lives imagined for “Tearing Down this Place,” where it’s the woman who’s walked out the door and the man who’s left crying in the “house I built for two.” Or, if you prefer, its an older, wiser version of the guy in “Don’t Fall in Love with a Lonely Girl,” done blaming and just wanting her to “Put your face up to mine and hold me in your arms.” What strikes me hardest, though, is just the music of it all. Freedy’s bereft tone and his beautiful, beseeching melody.

16. Freedy Johnston – “Darlin’” (from Back on the Road to You, 2022)

“Darlin’,” off Johnston’s most recent full length, has a slight country feel, thanks to the twangy acoustic up top and, especially, the way Doug Pettibone’s pedal steel sounds like its singing a duet with Freedy. Johnston has said in interviews that he had a more specifically sad narrative in mind here, but the details he gives us leave the domestic trauma vague. He did share the backstory with Aimee Mann, backing vocalist on the track, and she created a cartoon flip book telling the story for him. Johnston could only look at it one time, he’s said, because it so moved him. The song withholds details maybe but gives us enough: A man is telling his wife, who’s grieving what the song can’t say, “holding herself…” in the middle of the night. “Everything’s going to be all right, in the morning,” he tells her. No, it won’t. And she knows it won’t. But what a gift to have someone, who also knows that it will never be okay, to hold you tightly and say it anyway.

Freedy Johnston, 2/14/2026, at Eighth Street Tap Room in Lawrence, KS; with Jim Piller (bass), Jeremy Sidener (drums) and Heidi Gluck (keyboards, guitar, accordion).

(Want more installments of “A Love Letter in 16 Songs”? NFR has them for Elvis Costello, Joe Ely, Patty Griffin, Nanci Griffith, Ronnie Lane, Nick Lowe, The Mavericks, Maria McKee, Tom Petty, The Roots, Sammi Smith, Sly and the Family Stone, Swamp Dogg, Wilco, Brian Wilson, and Stevie Wonder.)

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