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.
This is truly a coin toss for me, because I love the work of both of these men. In the end, I’m going to go with Lovett for his versatility. Big band, country, pop, jazz… he does it all. I just hope he decides to start doing it again.
Haven’t laughed this hard in a long time
I better stop now before I start crying
Go off to sleep in the sunshine
I don’t want to see the day when it’s dying
She’s a sight to see (sight to see), she’s good to me (good to me)
But I’m already somebody’s baby
She’s a pretty thing (pretty thing) and she knows everything (everything)
But I’m already somebody’s baby
You don’t deserve to be lonely
But those drugs you got won’t make you feel better
Pretty soon you’ll find it’s the only
Little part of your life you’re keeping together
I’m nice to you (nice to you), I could make it through (make it through)
But you’re already somebody’s baby
I could make you smile (make you smile) if you stayed a while (stayed a while)
But how long will you stay with me baby?
Because your candle burns too bright
Well, I almost forgot it was twilight
Even if I think that you are right
Well, I’m tired of being down, I got no fight
You’re wonderful (wonderful), when it’s beautiful (beautiful)
But I’m already somebody’s baby
And if I went with you (went with you) I’d disappoint you too (disappoint you too)
Well, I’m already somebody’s baby
Already somebody’s baby
Meet Me In Montauk 
Well, this isn’t close for me at all. I appreciate Elliot, but Lyle is an all time favorite. I too wish he would release more original music, but, much like the Beatles or Billy Joel, if he never does give us more new offerings, what he he has already given us puts him up there among the best.
Recently I have gotten to know Elliot Smith’s music better because of a cover Ben Folds did for the A.V Club of “Say Yes” which led me down a bit of a rabbit hole. I very much appreciate his melancholic lyrics and ability to set a story but nothing I’ve heard of his comes close to Lyle Lovett. If in the right mood I would even say Lyle Lovett is the best artist of all time, and though I do see what you’re saying about a lack of original work in recent years (though Natural Forces is a pretty good album I feel) his music prior to that is enough to stack up against any artists regardless how more prolific that artist may be.
I really can’t stand either artist but I am more aware of Lovett.
As you know, Lyle Lovett is my desert island artist, so this is the easiest pick yet (and likely will be for me throughout this contest).