Tag Archives: The Road to Ensenada

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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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Song of the Day #475: ‘Her First Mistake’ – Lyle Lovett

lovettA few weeks back when I featured Lyle Lovett’s music for two weeks, I mentioned in my write-up of The Road to Ensenada that I would feature its two best songs on the blog at a later date. Well, that later date has arrived for one of them.

‘Her First Mistake,’ the epic second song on Lovett’s best album, is the tale of a man who strikes out so winningly in trying to woo a lady that she eventually succumbs to his charms. It’s funny and sweet and it’s got a swinging, almost bossa nova, feel that sets it apart from the rest of Lovett’s work.

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Song of the Day #424: ‘Fiona’ – Lyle Lovett

ensenadaAnd so it came to pass that, in 1986, Lyle Lovett released his finest album, The Road to Ensenada. Lovett’s early albums are so uniformly excellent that it’s difficult to single one out as number one, but Ensenada blends some of his best songs with perfect performances and production and it’s also his most successful marriage yet of the heartfelt and the humorous.

On the heartfelt side, you have several songs inspired by his divorce from Julia Roberts, just a year or so after their unlikely marriage. I remember I was living at home when Lovett and Roberts married and my mother told me the news one morning when I was half asleep. When I made my way downstairs, I had to ask her if I’d dreamed that conversation. It was that bizarre a concept.

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