Round Three of Montauk Madness should be the most difficult yet, and this matchup certainly fits the bill. Two piano-playing singer-songwriters from different generations, both comfortably outside the mainstream. Randy Newman vs. Fiona Apple.
Newman defeated Adele with 90% of the vote in Round One, then The Rolling Stones with 89% in Round Two. Apple took down Dar Williams 80/20 in the first round before winning a tougher contest (60/40) against Brad Paisley.
I love both of these artists wholeheartedly. Newman is the more prolific of the two (especially if you factor in his movie soundtrack work) which could give him the nod, but I’ve spent more time listening to Apple’s music. Apple is probably more consistent, but that’s easier when you’ve released only four albums.
I’m happy to see either of these artists advance, and I’ll be sad to see either left behind.
I’m going to wimp out and make my pick a more practical consideration. I’m almost positive Randy Newman will win this contest, regardless of how I vote. So like a senator who votes to repeal Obamacare when Obama is in office, knowing full well it won’t really happen, I’m going to cast a symbolic vote for Fiona Apple here.
That way, while I’m happy to see Newman move on, I’m not personally responsible for Apple’s demise.
🎵 More Fiona Apple 🎵
→ My Fiona Apple Deep Dive
→ A detailed appreciation of Fetch the Bolt Cutters
→ Line-by-line analysis of ‘I Know’
🎵 More Randy Newman 🎵
→ All of my Randy Newman coverage
[Verse 1]
In Germany before the war
There was a man who owned a store
In 1934
In Düsseldorf
And every night at 5:09
He’d cross the park down to the Rhine
And he’d sit there by the shore
[Chorus]
I’m looking at the river
But I’m thinking of the sea
I’m thinking of the sea
I’m looking at the river
But I’m thinking of the sea
[Verse 2]
A little girl has lost her way
With hair of gold and eyes of gray
Reflected in his glasses as he watches her
A little girl has lost her way
With hair of gold and eyes of gray
[Chorus]
I’m looking at the river
But I’m thinking of the sea
Thinking of the sea
Thinking of the sea
[Verse 3]
We lie beneath the autumn sky
My little golden girl and I
And she lies very still
Meet Me In Montauk 
I appreciate Apple’s considerable talent, but Newman has been one of my favorite artists for decades. He gets my vote here. Sorry Fiona.
I considered for about a second voting the way you did because I do appreciate Apple’s talent and want to support the few female artists in this contest. That said, I couldn’t ultimately bring myself to vote against the man responsible for both songs that move me deeply (such as “Home” and “When She Loved Me”) and a song that has been a staple of every introductory lesson on satire I have ever given. I use “Political Science” for that purpose, though Newman has at least a half dozen other songs which could work just as well. Finally, seeing him live years ago cemented my love for his humor and his artistry. So, yeah, it’s Newman for me.
Yes there aren’t many female artists in this competition but I’m gonna vote for Randy Newman regardless.