Song of the Day #1,475: ‘The Girl With the Holiday Smile’ – Lyle Lovett

I’m more than a little fed up with Lyle Lovett.

Since his 1996 masterpiece, The Road to Ensenada, he has released seven albums, and he doesn’t appear to be trying on any of them. That group includes a soundtrack, a live album and three records dedicated almost exclusively to covers.

The other two albums — My Baby Don’t Tolerate and It’s Not Big It’s Large — have their moments but mostly sound like Lovett is going through the motions, coasting on the reputation he established over his amazing first six records.

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Song of the Day #1,395: ‘Here I Am’ – Lyle Lovett

Best Albums of the 80s – #10
…and His Large Band – Lyle Lovett (1989)

The AllMusic review of Lyle Lovett’s third album, Lyle Lovett and His Large Band, describes the record as a spectacular way to burn bridges to the traditional country and western establishment.

Indeed, if his previous effort, Pontiac, hadn’t made it clear that Lovett was as interested in gospel and jazz as country, this record surely drove that point home.

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Song of the Day #1,369: ‘That’s Right (You’re Not From Texas)’ – Lyle Lovett

Best Albums of the 90s – #7
The Road to Ensenada – Lyle Lovett (1996)

Lyle Lovett’s sixth album, The Road to Ensenada, was the logical culmination of everything he’d done before. It struck a balance between his country and jazz sides, leaning a bit toward the former, but it didn’t have the schizophrenic feel of And His large Band… or Pontiac.

On those records, Lovett basically dedicated a side apiece to his country work and another side to his big band and gospel sound. On Joshua Judges Ruth he scaled the country back and sometimes strayed too far into sleepy ballad territory.

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Song of the Day #987: ‘It Ought to Be Easier’ – Lyle Lovett

So we have reached the final installment in my 20-day series on great albums. Singing us out is Lyle Lovett and his 1996 album The Road to Ensenada.

Lovett’s albums tend to suffer from multiple personality disorder. His influences are so broad and his style so far-reaching that his records often end up as a hodgepodge of great ideas. He dabbles in country, jazz, blues, rock and gospel, making for wonderful songs but schizophrenic albums.

The Road to Ensenada avoids that confusion. It’s a straightforward collection of traditional country and honky-tonk and, though it is less expansive than his earlier work, it remains the best thing he has ever done.

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Song of the Day #592: ‘The Road to Ensenada’ – Lyle Lovett

Last September, during a Lyle Lovett theme week, I singled out one song from his album The Road the Ensenada and promised to highlight two other songs — the album’s best — on future dates. I fulfilled half of the promise in November, when I featured ‘Her First Mistake‘ as a Song of the Day. Today I complete the mission.

For my money, the title track of The Road the Ensenada is possibly the finest song Lovett has ever written, and among the finest I’ve ever heard. That’s high praise for a relatively simple song but Lovett is no stranger to high praise, at least from this corner.

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