I’ve always said that I don’t have a favorite song, but there is one song I know for certain has to be on any list of my five or ten favorite songs, and that is Fiona Apple’s ‘I Know.’ This heartbreaking ballad is the final track on Apple’s 1999 album When the Pawn… and it’s a stunner.
Supporting her debut album Tidal, she demonstrated the combination of poise and nervous awkwardness she would exhibit throughout her career.
As with most of these challenges, I can interpret this one in different ways. Aside from the romantic reading, I could go with a song that breaks my heart because it has sad associations. I’m tempted to pick John Lennon’s ‘Imagine,’ which has come up a few times already, because hearing it while thinking about John Lennon’s fate is indeed heartbreaking.
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.
Brad Paisley took out Lana Del Rey in Round One of Montauk Madness, and now he faces another enigmatic female singer-songwriter in Fiona Apple. Apple is both a better singer and a better songwriter than Del Rey (which is high praise for her, not a shot at Del Rey), but does she have the stuff to take out one of country music’s leading men?
Paisley picked up 75% of the vote in defeating Del Rey, while Apple defeated another female singer-songwriter, Dar Williams, with 80%. Continue reading
Just yesterday I was discussing the tough road female artists have had in Round One of Montauk Madness, thanks to the luck of the draw in the matchups. Here’s another example, where two very talented women have to face off against each other (the first such battle, unless you count Lucinda Williams taking on the Shirley Manson-led Garbage).
Dar Williams is a relatively obscure artist who has quietly released almost a dozen albums of literate folk pop. She is a master lyricist and knows her way around a melody, and she’s responsible for one of my very favorite songs, ‘When I Was a Boy.’
#3 – Fiona Apple – The Idler Wheel…
Fiona Apple released my second favorite album of the 90s (When the Pawn…) and my second favorite album of the 00s (Extraordinary Machine). Here she sits in the #3 spot for the 10s.
That’s a hell of a streak. Imagine if the woman put out more than one album per decade.