Song of the Day #3,255: ‘Twilight’ – Elliott Smith vs. Lyle Lovett

Today’s Montauk Madness first round matchup is one of the hardest to date. The beautiful melancholy of Elliott Smith against the wry virtuosity of Lyle Lovett. One man whose career was cut tragically short by suicide and another who seems to have stopped recording new music altogether after a brilliant decade-long run from 1986-1996.

What exactly happened to Lovett after the ’96 release of The Road to Ensenada, his best album? He released seven albums over the next 20 years, almost all of them covers albums.

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Song of the Day #2,771: ‘Record Lady’ – Lyle Lovett

iloveeverybodyHere’s one of those fun cases where the birthday of a loved one falls on a Random Weekend.

It gives me a chance to play my favorite musical game, wherein I say “whatever song plays next will sum up the rest of your life” or “whatever song plays next describes our marriage” and so on.

So, whatever song plays next is dedicated to my lovely daughter Fiona, who turns 10 today.

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Song of the Day #2,616: ‘All My Love is Gone’ – Lyle Lovett

joshuajudgesMy fourth favorite album of 1992 is Lyle Lovett’s fourth studio album, Joshua Judges Ruth. This was the first new material released by Lovett since I’d discovered his jazz-blues-country masterpiece …and His Large Band.

Joshua Judges Ruth, cleverly named after three consecutive books of the Bible, strayed even further from Lovett’s country roots. The only true country tune here is ‘She’s Leaving Me Because She Really Wants To.’ Lovett’s deadpan humor isn’t on display here, either, as most of these songs deal with loss of love or life.

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Song of the Day #2,508: ‘Pantry (Acoustic Version)’ – Lyle Lovett

naturalforcesEvery several months a Lyle Lovett song pops up on Random Weekends, and every several months I bemoan the fact that the man hasn’t put out an album worthy of his talents in nearly two decades.

The Road to Ensenada, Lovett’s best album, came out in 1996. In the 19 years since, he’s put out five studio albums, three of which consisted mostly of covers. The other two were pale imitations of the great albums he released during the first decade of his career.

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