A grin through gritted teeth—Dwight Yoakam’s “Try Not to Look So Pretty” makes desire sound like discipline, the kind of self-talk you give yourself when the heart wants what pride is trying to refuse.
Let’s anchor the facts before we follow the feeling. “Try Not to Look So Pretty” was issued in February 1994 as the fourth single from This Time (Reprise, released March 23, 1993). It’s co-written by Dwight Yoakam and Kostas, produced by Pete Anderson, and it reached No. 14 on Billboard’s Hot Country Singles & Tracks and No. 4 on Canada’s RPM Country Tracks. The parent album—Yoakam’s commercial zenith—went triple-Platinum and peaked No. 4 on Top Country Albums.
If you like your memories with pictures, there’s a music video directed by Gregory (R.) Alosio—all telecasters, attitude, and that wry Yoakam half-smile that says he knows he’s losing the argument with himself.
What the record does, especially for older ears, is sneak a prayer into a swagger. On paper, it’s a plea—please don’t make it harder by looking that good—but the performance lands like grown-man candor. The band moves in an easy Bakersfield lope: drums sit a breath behind the beat (reassuring, not insistent), the bass nudges the bar line forward, and the guitars answer Yoakam’s phrases with short, conversational flickers instead of hot-shot runs. That’s Anderson’s production superpower across This Time—leave air around the singer, trust the pocket, don’t oversell the joke.
The writing matters. Pairing Yoakam with Kostas was a 1990s country sweet spot: plain words doing heavy lifting, melody that walks rather than struts, and a point of view that’s tender even when it’s trying not to be. There’s no courtroom in this lyric, no grand moral—just the everyday dignity of someone trying to keep his cool while the room tilts. And that’s why it wears so well with time. When you’re young, it plays like clever bravado. Years later, it sounds like self-knowledge sung with a wink.
Part of the song’s warmth comes from the players who make it breathe. The album’s personnel reads like a West Coast country all-star call sheet—Pete Anderson on electric guitar, Jeff Donavan on drums, Taras Prodaniuk on bass, Skip Edwards on keys, Al Perkins adding steel and dobro, with strings arranged by Paul Buckmaster elsewhere in the set. They give this track a human scale: the snare’s dry snap feels like a screen door closing gently; the keyboards glow like lamplight; the guitars witness and step back. It’s craftsmanship that knows how to serve a line.
Placement on the record tells its own story. This Time is that rare country album with five charting singles—three of them Top-2 smashes—and Yoakam threads the hits with interior scenes: kitchen-table laments (“Home for Sale”), bruised poise (“A Thousand Miles from Nowhere”), and then this one, a sly mid-tempo that turns the tension between willpower and want into a rhythm you can live with. By the time “Try Not to Look So Pretty” hit radio in early ’94, listeners already trusted the album; this cut felt like the late-chapter confession you didn’t know you needed until you heard it.
There’s a bit of era context, too. Country radio in ’93–’94 was crowded with big, declarative choruses. Yoakam takes another route: scale everything down. The hook lands with an almost conversational ease, and the humor is gentle, not jokey. Older listeners recognize that tone—the way affection and aggravation mingle when two people know each other’s habits a little too well. It’s not a tantrum; it’s a smile with teeth, backed by a band that understands the value of leaving something unsaid.
Play it again tonight and notice the little mercies. The beat never hurries you; it steadies you. The guitars answer, then withdraw, like good friends who know not to crowd you while you’re talking yourself off a ledge. And Yoakam’s vocal—those careful consonants, that slight downward smile on the title line—refuses melodrama. He doesn’t beg. He admits. That’s why the song still lands: it treats desire as something a decent person can hold without breaking anything.
Scrapbook pins, neat and true
- Artist: Dwight Yoakam
- Song: “Try Not to Look So Pretty” — writers: Dwight Yoakam / Kostas; producer: Pete Anderson; released as fourth single from This Time in Feb 1994; US Country #14, Canada Country #4.
- Album: This Time (Reprise, Mar 23, 1993) — triple-Platinum; Top Country Albums #4. Core players across the album include Pete Anderson, Jeff Donavan, Taras Prodaniuk, Skip Edwards, Al Perkins.
- Video: directed by Gregory R. Alosio (Yoakam appears throughout).
Sometimes the bravest thing a song can do is tell the truth without raising its voice. “Try Not to Look So Pretty” does exactly that—three generous minutes of rhythm, restraint, and a man trying to behave himself in the presence of someone who makes that very, very hard. And it leaves you with the kind of smile that lasts past the fade.