The five best covers by Fiona Apple

According to her long-time housemate Zelda Hallman, Fiona Apple doesn’t listen to any music at all when she is working on a new project.

Presumably, this is so that she can hear more clearly her own thoughts and ideas, and not be swayed into too heavily following in somebody else’s footsteps, picking up on their muse or inspiration, but being intuitively led by her own. Conversely, Apple is an artist who is deeply inspired, rooted and powered by the music that came before her.

You wouldn’t try to make a movie without ever having immersed yourself in a life of films, or try to write a book without ever having stepped inside the stories of a hundred great novels. In fact, even one of our greatest ever writers, Joan Didion, taught herself to write by copying out the works and worlds of Ernest Hemingway so that she could better understand the inner mechanics, technicalities and rhythm of his writing. We could all do a lot worse than to do something similar with Didion’s own work and then go from there. 

Before anybody begins to write their own songs, they first need to fall under the spell of other people’s music. They need to be enchanted by the magic of songwriting itself, and to undertake an education in a wide range of styles, modes, forms and genres. Sure, it helps if you have a natural way with words, but even Bob Dylan wouldn’t have become as good a songwriter as he did without first totally immersing himself in the whole history of song. And you can usually tell how good somebody’s musical education was by the kinds of songs they like to cover; you can tell how deep and how broad their studies have been, and then you can find the lessons they learned turning up in their own songs, whether consciously or unconsciously.

Revisit Fiona Apple's dreamy cover of The Beatles song 'Across the Universe'-2
Credit: YouTube

Fiona Apple is arguably the greatest contemporary songwriter working in the English language (who else would be up there with her? Probably people like Adrianne Lenker, Jeff Tweedy, Courtney Barnett, Daniel Romano and a whole bunch of young or independent artists who haven’t made it ‘big’), but she is also one of our great song interpreters, too, if not the best. Her range of covers is staggering, and also the range of emotions, voices, moods and feelings that she can set with every song she sings.

She can pay tribute and respect to the great singers and songwriters who went before her, while simultaneously making their work sound like her own. It’s a fine tightrope that she walks, but one which she always pulls off with aplomb.

Before we get into the list of her five very best covers from throughout the years, let’s just take a quick run through some honourable mentions, but this is by no means an exhaustive list. ‘Don’t Get Around Much Anymore’ by Duke Ellington, ‘Please Send Me Someone to Love’ by Percy Mayfield, ‘Across the Universe’ by The Beatles, ‘After You’ve Gone’ by Turner Layton and Henry Creamer, ‘Every Day’ by Buddy Holly, ‘Tonight You Belong To Me’ by Billy Rose and Lee David, ‘Blue Skies’ by Irving Berlin, ‘Crazy’ by Willie Nelson, ‘Let Me Roll It’ by Paul McCartney and Wings, ‘Jolene’ by Dolly Parton, ‘Lately’ by Don Heffington, ‘The Whole of the Moon’ by The Waterboys, ‘Heart of Gold’ by Neil Young, and ‘He’s Funny That Way’ by Neil Moret, Richard Whiting.

It’s always exciting to get new music from Fiona Apple, but unlike with a lot of artists, it’s just as exciting when she releases a new cover.

Here are the five best covers from Fiona Apple:

‘Tombstone Blues’ (Bob Dylan cover)

Fiona Apple - 2015 - Musician

Whether it’s working closely with multi-instrumentalist and producers Jon Brion and Mike Elizondo over the years, or else duetting with artists as diverse as Johnny Cash, Elvis Costello, Andrew Bird and King Princess, Fiona Apple understands the musical spirit of collaboration. While she often shies away from the solo spotlight on stage, she has often enjoyed performing live with the Watkins Family Hour band, a musical revue that rolls all the way through the history of American song.

And nobody has done more for the history of American song than Bob Dylan. Apple has always loved him and his music, and that love comes through in her vocals when singing his 1965 song ‘Tombstone Blues’, but so too does her sense of enjoyment at performing with the Watkins Family Hour & Friends, as she teases and toys with every word and every syllable, ripping and roaring her way through one of the more upbeat songs she’s ever performed. Incidentally, also on stage were Bob Dylan band alumni Al Kooper and Benmont Tench. Apple herself would go on to play piano with Dylan on one of his greatest ever songs, ‘Murder Most Foul’, in 2020.

‘Walkin’ After Midnight’ (Patsy Cline cover)

Fiona Apple - Shadowboxer - 1996

‘Walkin’ After Midnight’ is one of those songs where everybody knows that there is one singular, definitive version, and that is Patsy Cline’s, who set the standard with her seminal 1956 recording, and since then, nobody has sung it as well as her, let alone better, until Apple came along.

In 2007, the singer summoned and conjured the long-gone power of Patsy Cline, sounding like she was singing through the ages, and channelled all the heartbreak of Cline’s weeping-willow voice. Though she is comfortable moving through the genres and moving through the gears, so often when singing other people’s songs, Apple leans into America’s history of jazz. However, here she showed she could hold her own with the very best of them in the country of country if she wanted to, as well, which makes you wonder what she could do with songs like ‘There Stands the Glass’, ‘You Win Again’, ‘Miss the Mississippi (And You)’, ‘I Fall to Pieces’ and countless other country tunes.

‘All Alone’ (Irving Berlin cover)<br>

Fiona Apple - O' Sailor - 2005

If Fiona Apple is one of our greatest contemporary songwriters, then when we talk about Irving Berlin, we are talking about one of the greatest songwriters of all time, and I would never want to imagine living in a world without songs like ‘Blue Skies’, ‘Cheek to Cheek’, ‘How Deep is the Ocean?’, ‘I’ve Got My Love to Keep Me Warm’, ‘Let’s Face the Music and Dance’, ‘Puttin’ on the Ritz’, ‘What’ll I Do?’ or ‘White Christmas’.

If the lines that he wrote oh-so-long ago, “I’m all alone every evening, all alone feeling blue /
Wondering where you are / And how you are / And if you are / All alone, too?” are not devastating enough by themselves, then just wait until you hear them in Apple’s piercingly, achingly and heart-beakingly delicate, fractured and fractal voice; it’s one of the most moving and powerful performances you’re ever liable to hear.

‘Why Try to Change Me Now?’ and ‘I Walk a Little Faster’ (Cy Coleman covers)

Fiona Apple - Every Single Night - 2012

Fiona Apple, if you’re reading this, please, please, please, can we have an album dedicated to jazz standards one day?

The thing about the songs of the Great American Songbook and all the jazz standards that we know and love is that everybody sings them. Not just all the old greats like Ella Fitzgerald, Billie Holiday, Sarah Vaughan, Bing Crosby and ‘Ol’ Blue Eyes’ himself, but singers that you might not expect have been drawn to them, too, like Dylan, Paul McCartney, Rod Stewart, Willie Nelson, Linda Ronstadt, Lady Gaga, Alicia Keys, and of course, Fiona Apple.

Apple doesn’t just sing them as well as anybody, but she sings them better than most, as evidenced by the two stunningly gorgeous covers she contributed to the 2009 tribute album The Best Is Yet To Come – The Songs Of Cy Coleman. Though the disc also boasted performances by great singers like Patty Griffin, Madeleine Peyroux, Perla Batalla and Sara Watkins, Apple’s vocals on ‘Why Try to Change Me Now’ (which could have been written about her) and, maybe especially, ‘I Walk a Little Faster’ stand head and shoulders above anything else on the album.

‘River Stay Away From My Door’ (Mort Dixon and Harry M Woods cover)

Fiona Apple - Fetch The Bolt Cutters - 2020

The LA nightclub Largo has acted as something of a home base for Fiona Apple over the years, and while the famously shy and semi-reclusive performer can be tentative about going on tour, she has made countless appearances onstage with friends in Largo over the years, and immortalised such a scene and such a night in her song of the same name on her 2012 album The Idler Wheel.

And fittingly, Largo was the scene of one of her greatest ever performances, one which showed off her entire range of singing styles and emotions. She moved around between subtlety and shouting throughout, rolling and raging like a mighty river herself, before switching to her head-voice for an exquisite finale. Like her renditions of ‘All Alone’, it’s another devastating performance, but it’s also one that is full of incredible fire and power, a real life force and virtuosity. Apple reaches into the ages on this one and sings with an elemental quality that not many other singers, outside of maybe Bessie Smith, Memphis Minnie or Billie Holiday can regularly conjure.

Like I said at the start, it takes a lot of work to become as good as Fiona Apple is, and Apple has put that work in well over the years, but she also happens to have the other ingredients you need to be an all-time great, as well: natural talent, easy genius, a lot of heart and, maybe most importantly, soul.

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