Song of the Day #3,393: ‘I Can’t Love You Anymore’ – Lyle Lovett

Day 28 of the 30 Day Music Challenge calls for ‘A Song By An Artist With a Voice That You Love.’ As usual, lots of great options here.

I might have gone with several artists I’ve already featured in this series, including yesterday’s pick, Fiona Apple, as well as Frank Sinatra, Tift Merritt, Elton John, Michael Stipe or Olivia Newton-John. But repeats are a no-no.

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Song of the Day #3,316: ‘Step Inside This House’ – Lyle Lovett vs. The Beatles

Here we are, at the last matchup in Round Three of Montauk Madness. Things are moving fast now; we’ll be down to the final eight artists next week.

This battle might seem like a laugher in the broader world, but around these parts I expect it will be a nail-biter. Lyle Lovett vs. The Beatles. Lovett got here by dispatching Elliott Smith with 89% of the vote in Round One before winning a tighter match against Bruce Springsteen (63/38). The Beatles unanimously defeated Shakira then toppled Ben Folds with 80%. This matchup will be the first real test of the Fab Four. Continue reading

Song of the Day #3,283: ‘She’s No Lady’ – Lyle Lovett vs. Bruce Springsteen

Arguments about artist selection, seeding and who should beat who aside, this Montauk Madness bracket system ultimately works, producing plenty of heavyweight matchups already.

Lyle Lovett vs. Bruce Springsteen is a doozy, pitting two of the best songwriters and lyricists I’ve ever heard against each other in just the second round.

Springsteen got here by dispatching John Mellencamp in a unanimous vote, while Lovett came close to his own sweep, besting Elliott Smith with 89%. Continue reading

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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