Lyle Lovett’s relationship with country music is a lot like Texas’ relationship with the South. It might technically be geographically correct to lump them together, but that’s obeying the letter of the law rather than the spirit. Sure, Texas might have been part of the Confederacy and Lovett’s first single was titled “Cowboy Man,” but it wouldn’t be Lyle, or Texas, if the letter wasn’t fiddled with so the spirit can roam free.

Lovett doesn’t fit the stereotypical cowboy mold and he certainly ain’t the country patriarch, AR-15 in one hand, Bible in the other. Lovett was a wannabe Lothario, and the only thing more caustic than his assessment of the world was his self-loathing. Opening instrumental standard “The Blues Walk” tells us this ain’t your normal rodeo and sets the stage for a crooner to waltz on stage with his crack backing band. Instead, Lovett’s first words are “Hello, I’m the guy who sits next to you and reads the newspaper over your shoulder/ Wait/ Don’t turn the page I’m not finished.”

“Here I Am,” with the aforementioned newspaper monologue sums up our narrator perfectly. Between belted declarations of love, he drops gems like this, “Look I understand too little too late/ I realize there are things you say and do you can never take back/ But what would you be if you didn’t even try/ You have to try/ So after a lot of thought I’d like to reconsider/ Please If it’s not too late/ Make it a cheeseburger.” His songwriting genealogy was a product of Joni Mitchell, Randy Newman and Warren Zevon, picking apart the minutiae for kicks.

This is Lovett’s central dynamic, one moment the lounge singer schmoozing his way out of his league, the next a nebbish nerd over-analyzing and using paradoxes as pick up lines. Or as he would put it “Serious reflection and massive rationalization/ For contemplating the future of the future/ And the last of the past.” He does manage to get in one rose-delivering romantic icebreaker “Tell me something you need/ Not just what comes to line/ ‘Cause I can see you’re somewhere in between/ This morning and the late last night.” but even those smooth-as-silk horn lines can’t save him from his worst tendencies.

“Crying Shame” starts as a jazzy bit of finger waving, with Lovett calling out an old flame who would “Spend the night/ Like you were spending a dime,” but she gets her revenge as voiced by Large Band star/counterbalance-to-Lovett’s ego, Francine Reed. “You look lovely my dear,” croons Lovett with Reed rolling her eyes “Thank you I’m fine!” Reed gets a proper duet on “What Do You Do/The Glory of Love” with the pair playing a jaded couple firing shots as the TV dinner sizzles in the microwave.

It takes six songs of this glorious schmaltz for Lovett to play a damn country tune, like “I Married Her Just Because She Looks Like You” was a last second addition to placate the record label. Of course, if you hadn’t noticed by the title, “I Married Her” isn’t quite the country chart topper MCA was hoping for. Lovett bitterly recalls a breakup while channeling that seething hate into extolling the loveliness of his wife—who, uh, does happen to look a lot like his ex. The song does mellow into something much less petty, with Lovett admitting “And if I had not searched for you/ I never would have found her/ And if I had not loved you/ I would never have known love” a surprisingly mature confession from a man who seemed to set up the whole song as a twangy middle finger. That’s followed by a stellar cover of Tammy Wynette’s “Stand By Your Man” and Lovett acknowledges the irony. When he sings “After all, he’s just a man” by way of apology, he sheepishly shrugs through his voice.

But it wouldn’t be a Lyle Lovett album without some tearjerkers between the goofs. “Which Way Does that Old Pony Run” first starts as a series of excuses and ramblings (“When I was a young man, I was a cowboy/ The best in the land”) but soon reveals itself to be a painful meditation on freedom and crises of the self and of the mid-life verity. Considering Lovett still lives in the hamlet of Klein, Texas, his words of “What’s riches to you/ Just ain’t riches to me/ And if you’re staying out here/ Then I’m headed back east” seems to be his permanent kiss off to California before retreating to his home. Micro ballad “Nobody Knows Me” starts as an ode to Lovett’s love of tortillas before reflecting on a recently burned out love. “If You Were to Wake Up” ends that sentence with “And I were beside you,” Lovett daydreaming of a sudden reunion with his old love. The possibility is just out of reach, torturing him in his half sleep. “Time reaches to you/ Just like a willow/ That bends to the water/ And clings to the shore.” Unlike the title track or “Simple Song” from Pontiac, Large Band’s sorrow is more measured and guarded but nonetheless devastated, making it all the more depressing.

But Lovett can’t close on a blue note. Instead the near acapella stroll of “Once is Enough” has him playing his most jaded dork. He quickly brushes aside any idea of future love (“Once is enough” after all) only to admit, in closing, that he’d be just fine with the pretty gal he’s been hanging around to give him the eyes, just once.

So Lovett ain’t the typical Texan, but Texas thrives off of weirdos. Being distinctly Texan in an unTexan way is the most Texan thing you could do. If that doesn’t make any sense to you, you need to spend more time in the Lone Star State, or at least cozy up to more of Lovett’s albums. You’ll come to understand the ornery devotion to being different that doesn’t just revel but actively finds vanity in oddballness.

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