I’ve had the conversation plenty of times now, but I’m always stunned when it takes place: Me and a friend or acquaintance, jawing about music, extolling the virtues of this or that songwriter, and when the subject turns to Lyle Lovett, I get an indifferent shrug.

“Eh,” the friend or acquaintance says. “Never really liked him.”

Now, Lyle Lovett has certainly piled up enough critical hosannas over the course of his career; I’m not suggesting that nobody likes him, or even that you probably don’t like him. I’m just saying that I often meet people who don’t. People whose tastes in music, I’d think, would match up squarely with the sort of hyper-intelligent country/folk/pop/jazz that Lovett specializes in. People who enjoy a finely drawn character sketch set to music, or a songwriter who can comfortably and believably inhabit the skin of a lovable ne’er-do-well.

These are people who should love Lyle Lovett. Perhaps you’re one of them. (If you’re a regular around here, I’m sort of inclined to think you are, but you never know.) Perhaps you’ve written Lovett off in the past as “country music,” a description that, though apt enough, misses the point. He’s a songwriter, first and foremost, and even if he isn’t one of the true greats, he comes close often enough to transcend such narrow labels. You may not like country music — I don’t particularly like it — but that doesn’t mean you won’t find a lot to love here.

Anyway, enough of my soapboxing. On with the music.

Lyle Lovett (1986)
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There are people who will tell you that Lyle Lovett is a classic album. I am not one of them.

It isn’t a bad record at all. It is, however, the sort of album that has to be seen in context to be truly appreciated. 1986 was sort of a dark year for country music; the genre was caught between the massively successful rhinestone hokum of the early ’80s and the neo-traditionalist, pop-inflected stuff that would resurrect country radio in a few short years. As a result, Lyle Lovett has a sometimes disconcerting neither-fish-nor-fowl feel to it; Tony Brown’s production contains enough distracting countrypolitan touches to make you snicker when you shouldn’t, and the songs are among the safest of Lovett’s career.

At the time, though, it was part of a mini-revolution in country music. Though country listeners would abandon Lovett as soon as his music started to cross over, in ‘86, he was all over the radio. Lyle Lovett spun off no fewer than five Top 40 country singles. The best of the bunch is probably “God Will” (download), a darkly sardonic harbinger of what was to come.

It’s toward the end of the record that Lovett starts to shake his limbs a little — “You Can’t Resist It” (download) is the best song The Eagles never wrote, and with “The Waltzing Fool,” “An Acceptable Level of Ecstasy,” and “Closing Time,” he delivers a back-to-back-to-back punch, displaying the sort of empathy and attention to detail that would lay the foundation for his career.

Pontiac (1987)
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In terms of that dated ’80s country sound, with Pontiac, Lovett still wasn’t entirely out of the woods. But he was getting there.

And the songs? Well, you could tell he was writing from a viewpoint a good deal more — for lack of a better word — skewed than the artists he typically shared playlists with; just two songs in, he’s already had Tonto tell the Lone Ranger to kiss his ass and referred to a woman as a “chipkicker redneck.” In terms of crimes committed against country in the ’80s, this certainly ranks well below those perpetrated by, say, Steve Earle or Carlene Carter (who famously promised to “put the ‘cunt’ back in country”), but in a genre that had theretofore prided itself on its staid, traditional nature, it rates a mention.

Elsewhere on Pontiac, Lovett starts to tinker more extensively with the formula — “L.A. County” (download) is a murder ballad with a breezy pop arrangement, “M-O-N-E-Y” is casually misogynistic blues, and the title track (download) cops such a plain Randy Newman vibe that it may as well have been written by Newman himself.

Like its predecessor, Pontiac was well-received, both critically and commercially; even in hindsight, though, it’s difficult to say that anyone could have had any idea what Lovett would do next.

Lyle Lovett and His Large Band (1989)
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And here is where the country audience officially bade Lyle Lovett farewell. Though “I Married Her Just Because She Looks Like You” was a modest country hit, and Lovett’s straight-faced take on “Stand By Your Man” earned him considerable press, for the most part, Lyle Lovett and His Large Band was a pop crossover album.

This wasn’t necessarily because of closed-mindedness on the part of country listeners, either; anybody would have had a hard time figuring out what to make of the opening tandem of Lovett’s cover of “The Blues Walk” and the musical monologue that is “Here I Am” (download) — not to mention the sly duet “What Do You Do/The Glory of Love” (download) and the infidelity blues of “Nobody Knows Me.”

It’s the kind of confounding, genre-busting album that critics love, in other words, and love Large Band the critics did indeed. Though his fortunes at country radio were dimming, Lovett was fast acquiring the sort of cachet that guarantees record deals (sadly, it also seemingly guarantees negligible record sales).

Joshua Judges Ruth (1992)
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Lovett’s fourth album rode in on a huge buzz — particularly for an artist whose releases had never gone better than gold — and perhaps that’s why Joshua Judges Ruth has always been a record that divides the fans. It was a potential source of dismay for many segments of his audience, actually; listeners who had learned to depend on Lovett for a healthy number of feel-good country swing numbers on every album, fans who enjoyed his black wit, and people who enjoyed the Large Band were all among the disenfranchised. Judges is a spare, somber record full of despair and heartbreak; a single listen to the chills-inducing “North Dakota” (download) puts the album’s vibe in a nutshell.

He’s too squirrelly an artist to record an entirely miserable album, though, so of course there are the stray uptempo numbers — the riotous “Church” (download), the loose closer “She Makes Me Feel Good” — but on the whole, this is a dark set of songs, matched by George Massenberg’s chilly, austere production.

Joshua Judges Ruth is my favorite Lovett record. I don’t know if this makes me a mopey bastard or what, but it’s true. From here on out, Lovett’s release schedule slowed down (way down), and his albums became a lot less eclectic. Depending on your point of view, this change resulted in albums that were either more cohesive or less interesting.

I Love Everybody (1994)
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I Love Everybody consists of songs Lovett wrote in the years leading up to his debut album, but it isn’t really your typical odds & sods collection; Lovett, ever the contrarian, recorded them anew for their first official release.

Albums like these often tend toward the somewhat embarrassing, but then again, most songwriters aren’t that talented. It’s interesting to compare this quirky set of tunes with the relatively normal bunch that he ended up recording for Lyle Lovett; it proves that, rather than growing into his idiosyncratic shoes as he went along, he was always the bastard son of Randy Newman and Townes Van Zandt — he was just waiting to prove it.

Everybody was recorded in the wake of Lovett’s marriage to Julia Roberts, and the peak of his celebrity; perhaps as a result, it’s got gobs of big names in the credits. No, seriously: Kenny Aronoff, Sweet Pea and Sir Harry, Rickie Lee Jones, Leo Kottke, Russ Kunkel, Arnold McCuller, Mark O’Connor, Lee Thornburg:the list goes on. (Roberts even does a backing-vocal turn.) It doesn’t really affect the material either way; these are eighteen relatively slight songs, all in all. That being said, songs like “Fat Babies” (download) and the title track (download) are no less enjoyable for their lack of earth-shattering songwriting — and “Creeps Like Me” (download) shows how well Lovett was cribbing Randy Newman, even as a wee tadpole.

The Road to Ensenada (1996)
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Having cleared his vaults with I Love Everybody, Lovett had no choice but to reveal himself as the decidedly non-prolific writer he was — The Road to Ensenada’s eleven songs arrived four years after Joshua Judges Ruth. Ensenada is a pretty straightforward set of songs, too; it’s definitely the most accessible album he had released since his debut. Again, whether this makes Ensenada a more cohesive or less interesting affair depends on your point of view.

Me, I liked Lovett when his songs were as unpredictable as his hair. There’s a certain amount of quirk here — “Her First Mistake” (download) and “That’s Right” are Lovett at his most pleasantly tongue-in-cheek, “Fiona” is enjoyably strange, and “Private Conversation” (download) is another of the pop/folk/country hybrids Lovett seems to churn out with absolute ease — but the whole thing still has a rather muted feel. It’s as though, with Large Band and Joshua Judges Ruth, Lovett scaled the mountain of pop ambition, and returned a humbler, less interesting man.

This sounds like an unkind dismissal of what’s essentially a very solid record — but it’s really only in comparison to what Lovett once suggested he could do that his later recordings fail to measure up. By any other standard, they’re examples of stellar, rock-solid songwriting and performance. Take that for whatever it’s worth.

Step Inside This House (1998)
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There’s a long, proud tradition in pop music of artists finding strange and comical ways to burn their way out of a record contract (The Parkerilla, Metal Machine Music, et cetera). Releasing a double-disc collection of covers isn’t as direct a message as, say, putting out an entire album’s worth of feedback, but it makes for a much more enjoyable listen.

So here’s the deal: Lovett decided to reach back to his Texas roots for this one, and record twenty-one (mostly) little-known works by songwriters from the state formerly known as Mexico. Being that Lovett didn’t write a note here, it’s sort of pointless to judge Step Inside This House on artistic merits, at least within the confines of an Idiot’s Guide to Lyle Lovett; all that’s left, then, is to judge it as a listening experience.

By those standards, it’s pleasant enough, if a bit on the mellow side (I speak from experience when I say it makes for lousy driving music, especially if the driver in question is motoring through the Arizona desert). For Texan musicologists, it’s an interesting second look at songs by Van Zandt, Steve Frumholz, Guy Clark, and a number of other local sons. For Lovett diehards, it makes for an intermittently interesting curio. The rest of the world, however, could probably have done without Lovett’s interpretation of songs like “Bears” (download) and the title track (download).

Live in Texas (1999)
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As a live performer, Lyle Lovett will never be as electrifying as, say, Cheap Trick; neither will he ever approach the often spellbinding intimacy of a David Wilcox. As a result, though Live in Texas is a thoroughly enjoyable listening experience, its value was primarily as a de facto greatest hits (at least until 2001, when the real thing came along) than an audio revelation. Lovett’s band is beyond tight, the live arrangements hew closely to their studio counterparts, and Lovett keeps his between-song patter to a ridiculous minimum, so the only difference here is in the crowd noise.

That has its own limited value, actually — it’s interesting to hear the rapt silence in “North Dakota” give way to applause when Rickie Lee Jones takes the stage, and the knowing laughter when Tonto tells the Lone Ranger to kiss his ass during “If I Had a Boat” (download), but the only song that really benefits from the live makeover is “You Can’t Resist It” (download) — and that’s because the production on the original was so damn weird.

Bottom line: As contractual-obligation releases go, as with Step Inside This House, you could do a lot worse. Just don’t go into it thinking you’re embarking upon essential listening.

My Baby Don’t Tolerate (2003)
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Lovett’s last studio album arrived after a four-year wait; this time, fans held on for seven years before he returned from the wilderness. Listeners could be forgiven for thinking Lovett’s switch to Lost Highway, Luke Lewis’ indie-with-major-label-funding, would result in a return to wonderfully eclectic form — but ’twas not to be. My Baby Don’t Tolerate is, more or less, The Road to Ensenada II — a solid, decidedly non-eccentric set of songs that plays to Lovett’s strength as a “straight country” performer.

To beat a dead horse right into the ground, how you feel about this depends on your point of view.

The songs certainly aren’t bad. Lovett has tossed off some trifles in his day, but I’m really not sure he’s ever released a truly bad song, and he doesn’t include any here. The flip side of that coin is that they’re a little more — for lack of a better word — ordinary than some of us would like to hear from the man.

Now, look, Lyle Lovett even on his worst day is a damn sight better than many other artists could ever hope to be; I’m not trying to warn you off Tolerate, or even really suggest that it doesn’t measure up to his older stuff. Just for me, personally, things were more entertaining back when he hopped all over the goddamn map. Framed against his catalog as a whole, songs like “Cute as a Bug” (download) and “You Were Always There” (download) fail to break new ground while also refusing to yield any.

Is Lovett in creative stasis? Has he gotten as good as he’s going to get? Chances are good that we’ll have to wait until the next decade to find out:but even if the answer turns out to be “yes,” it’s nothing to complain about. Here’s a songwriter who got off on the good foot, stayed there, and probably has a lot of good years left in him. If you haven’t found this out for yourself already, do it now.