Introduction
A honky-tonk grin with a tender catch in its throat—Dwight Yoakam’s “Always Late (With Your Kisses)” proves that a classic can be both tougher and kinder the second time around.
Let’s pin down the essentials first—so the memories have something solid to lean on. “Always Late (With Your Kisses)” is Yoakam’s Bakersfield-leaning cover of Lefty Frizzell’s 1951 country landmark (written by Lefty Frizzell and Blackie Crawford). Frizzell’s original spent a long run at No. 1 on the country charts in 1951 and became one of the signatures of his revolutionary vocal style. In Yoakam’s hands, the song arrived on Hillbilly Deluxe (1987) and was issued as the album’s fourth and final single in 1988, climbing to No. 9 on Billboard’s Hot Country Singles and No. 5 in Canada; the video was directed by Sherman Halsey. The parent LP was Yoakam’s second straight No. 1 on the Top Country Albums chart.
A word about lineage helps. Frizzell’s cut—A-side to “Mom and Dad’s Waltz”—was tracked in Dallas in May 1951 and released that July; it’s a pillar of honky-tonk phrasing, the place where a drawled syllable can feel like a caress and a reprimand at once. Yoakam keeps that emotional ambiguity, but he moves the furniture: the tempo leans forward, the Telecasters nip a little harder, and the shuffle walks with longer strides. In short, he takes a torch song and teaches it to lope. That respectful reworking is exactly what makes the cover breathe like something new instead of a museum piece.
On the Hillbilly Deluxe session card you can see how he pulled it off. Pete Anderson produces and plays the wiry, right-on-time guitar; Tom Brumley (yes, from Buck Owens’s Buckaroos) sighs on pedal steel; Greg Leisz adds lap steel; the core Yoakam band—JD Foster on bass, Jeff Donavan on drums, Brantley Kearns on fiddle, Skip Edwards on keys—locks into that unshowy pocket Yoakam favored in the late ’80s. It’s textbook Bakersfield via Los Angeles: clean lines, lots of air, every lick answering the vocal and then stepping out of the way.
If you remember the period from country TV, the Halsey video gave the single a warm, amber glow—barroom lights, loose-hipped rhythm, no need to oversell what the lyric already knows. That visual tone matched radio perfectly in 1988: a throwback feel built with contemporary sharpness, the way a good Western shirt looks fresh because the stitching is immaculate.
What does the song say—now, with some years on the tires? Underneath the easy swing is a small admission older listeners recognize: late isn’t only about the clock; it’s about care. Frizzell’s narrator shrugs and aches at once; Yoakam preserves that ache but trades the shrug for a steadier spine. You can hear it in how he leans into “always late” without turning it bitter. He sounds like a man who’s decided to love the truth as it is: this is who she is, this is how he feels, and between those poles sits a dance step he knows by heart. That gentle firmness—grown-up patience without self-pity—is the update Yoakam brings to the room.
There’s also the pleasure of craft. Listen to the way the rhythm section nudges instead of pushes; how the steels flicker like neon on wet pavement; how the guitar fills are short, conversational phrases, never crowding the line. That economy is why the record still fills a kitchen or a garage just right: it respects your space. And it’s why the single’s chart run felt inevitable even in a year crowded with flashier productions; the song carries itself like someone who doesn’t need to raise his voice to be heard.
Context matters, too. Hillbilly Deluxe came hot on the heels of Guitars, Cadillacs, Etc., Etc., and its four singles—“Little Sister,” “Little Ways,” “Please, Please Baby,” and “Always Late (With Your Kisses)”—all landed in the Top 10, a statement that traditional bones could still flex on modern radio. Folding this Lefty standard into that streak was more than tribute; it was a thesis: the old grammar still writes beautiful sentences if you say them clean.
For the scrapbook you keep by the turntable: Artist: Dwight Yoakam. Song: “Always Late (With Your Kisses)”—written by Lefty Frizzell & Blackie Crawford. Yoakam version: on Hillbilly Deluxe (1987); released as fourth single in 1988; US Country No. 9, Canada Country No. 5; video director: Sherman Halsey. Source classic: Lefty Frizzell’s 1951 No. 1 smash, a cornerstone of his style and a long-running chart topper.
Spin Yoakam’s cut again and notice how it changes the room. The beat keeps your shoulders easy; the steel opens the windows; the vocal tells the truth without tightening its jaw. That’s the gift of this cover: it lets Lefty’s lonely wisdom live on, but it hands it to you with a little more daylight—like a familiar photograph, newly cleaned, where the eyes look the same and somehow kinder.