Certain Songs #1058: Lyle Lovett – “It Ought to Be Easier”

Album: The Road to Ensenada
Year: 1996

Nobody knew it at the time, but The Road to Ensenada marked the end of the first phase of Lyle Lovett’s career.

He’d put out six albums of original material in a decade, but after that, it seemed like the well kinda dried up, as he followed it with a covers album, a live album, a movie soundtrack, and two compilations before putting out another record of new material in 2003.

But meanwhile, back in 1996, we were just enjoying songs like the brutal breakup tune, “It Ought To Be Easier.”

Maybe it was about the breakup of his marriage to Julia Roberts, maybe it wasn’t; either way, “It Ought To Be Easier” was absolutely unsparing with its emotional directness.

And it ought to be easier
When you turn your lights down low
And it ought to be easierrrrrrrrr
To leave when you know that you have to go

In the first three lines of that chorus, Lovett is supported by a choir of backing vocalists and near-anthemic drum crashes on nearly syllable, but after the second “easier,” they all abandon him to sadly murmur “To leave when you know that you have to go” and you can’t help but feel for him. Even if he was in the wrong.

About halfway through, the whole song breaks down, and there’s long, sad fiddle solo from Stuart Duncan, who provides color for the rest of the song, and swirls around the last, heartbreaking verse.

See the sun comes up on the pavement
The pavement it starts to sweat
The steam rises up from the water
And the hotter it is you know the harder it gets
The hotter it is you know the harder it gets
The hotter it is you know the harder it gets

Of course, the beautiful thing about “the hotter it is you know the harder it gets” is that it can apply to just about any situation, as well as the catchiest part of the song, and so that was what brought me into the rest of “It Ought To Be Easier”

One of the reasons that The Road to Ensenada won the Grammy for Best Country Album in 1997, “It Ought To Be Easier” was released as a single, but was probably too sad and off-brand and subsequently went nowhere on the charts, even as the album itself went as high at #24 (and #4 Country) back when that actually meant something.

“It Ought To Be Easier”

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