Introduction
A tender, two-step confession—the kind you whisper after midnight—about pride giving way to honesty and hurt turning into something you can live with.
Essentials up front. Song: “It Only Hurts When I Cry.” Artist: Dwight Yoakam. Album: If There Was a Way (Reprise; released October 30, 1990). Writers: Dwight Yoakam and Roger Miller—one of the last songs Miller finished before his passing in 1992. Single release: December 21, 1991 (B-side: “Let’s Work Together”). Producer: Pete Anderson. Chart peaks: No. 7 on Billboard Hot Country Songs (U.S.) and No. 4 in Canada (RPM Country Tracks). Video: black-and-white clip directed by Piers Plowden.
What makes “It Only Hurts When I Cry” endure isn’t flash; it’s plainspoken strength. Yoakam sings like a man who’s finally done bluffing—shoulders squared, voice easy and unforced, admitting the ache without turning it into theater. The band, guided by Pete Anderson, keeps everything lean: Telecaster answers in short phrases, steel sighs in the margins, drums and bass hold a slow two-step that lets the lyric breathe. It’s the Bakersfield virtues in modern clothes—dry, close, and honest—exactly the sound Yoakam and Anderson perfected across If There Was a Way.
The lyric, co-written with Roger Miller, carries that unmistakable Miller touch: a simple line that lands like a lifetime. “It only hurts when I cry” reads like a wisecrack at first; in Yoakam’s mouth it becomes a truth you say to get through the day. There’s no clever twist, just grown-up clarity: the pain is real, and naming it doesn’t make you weak. Knowing this was among Miller’s final compositions lends the song a quiet gravity; it feels like an elder songwriter handing down a tool—language sturdy enough to carry sorrow—and a younger artist putting it to work. (The single’s credits and chart run confirm the Yoakam/Miller authorship and its Top 10 U.S./Top 5 Canada finish.)
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Placed in the arc of If There Was a Way, this was the fourth single in a remarkable streak—after “Turn It On, Turn It Up, Turn Me Loose,” “You’re the One,” and “Nothing’s Changed Here”—with “The Heart That You Own” still to come. That sequence matters: the album shows Yoakam moving from neon bravado to accountability, and “It Only Hurts When I Cry” is the moment where the mask slips all the way off. The record proved he could cut barroom stompers and still speak softly enough to be believed, a balance that kept him lodged on country radio through the early ’90s.
Listen for the small choices that make it live. The tempo never hurries; Anderson’s guitar doesn’t grandstand; the steel doesn’t weep so much as answer the vocal, like a friend nodding along at the kitchen table. Yoakam phrases just behind the beat—his trademark laid-back drawl—so the hook falls warm instead of brittle. At 2:34, the song honors 45-rpm economy: say your piece, say it true, and leave the chorus echoing in the room. (Collectors will note the single’s label details—Reprise 19148, recorded in 1990—and that Plowden’s monochrome video matches the song’s unadorned heart.)
If you were there in 1991–92, you remember how it felt on the dial—familiar as an old saying, fresh enough to hush a room. Country radio had plenty of kiss-offs and drinking songs; this one sat in the harder space between, where you admit the damage and still go to work in the morning. That’s why older ears keep it close. It respects consequences. It trusts restraint. And it lets a great melody carry a hard truth without turning it into a sermon.
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In the long view, “It Only Hurts When I Cry” is a small masterpiece of craft over spectacle. It carries the lineage Yoakam champions—Bakersfield bones, Roger Miller’s songwriter’s wit—while sounding entirely like itself. More than three decades on, it still does the quiet work you ask the best country records to do: make room for feeling without making a mess of it. Put it on, and you can almost see the old console stereo, the late-night kitchen light, and the way a simple chorus can steady your hands. That’s not nostalgia; that’s good writing, good playing, and a singer who knows when to let a song speak plainly.
Verified facts at a glance: Song: “It Only Hurts When I Cry.” Artist: Dwight Yoakam. Album: If There Was a Way (Reprise; Oct 30, 1990). Writers: Dwight Yoakam, Roger Miller. Producer: Pete Anderson. Single released: Dec 21, 1991 (B-side “Let’s Work Together”). Chart peaks: US Country No. 7, Canada Country No. 4. Video: Piers Plowden, black-and-white.