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Weekend Reads: Fiona Apple Edition

Updated: Aug 30, 2023


Stories like Mayweather’s and Lohan’s provide Americans with a certain schaudenfreude. There is an undeniable pleasure in seeing callow, self-satisfied one-percenters run afoul of the law and, in turn, have society remind them that there are greater forces than their chequebooks at work in this world. Put another way, the 99%’s collective enjoyment of celebrity imprisonment makes us all momentary Marxists. In savoring the stupidity, hubris, and punishment of the privileged, we feel a collective satisfaction that mitigates the frustration felt over the preposterous rewards given to people who make the most paltry of contributions to society.

Apple’s most famous moment (don’t worry, we’ll get to it…)


On the surface, Fiona Apple fits into the mould of a celebrity whose downfall we might enjoy. A singer-songwriter who has been a millionaire – with all of money’s attendant privileges – for her entire adult life, Apple is the latest star to make the case that she has been unjustly treated by “the man” after being arrested for – and admitting to – breaking the law. In most cases, I myself would mock Apple for the misplaced chutzpa she showed in trying to transport drugs over the Mexican border, as well as for her subsequent eagerness to whine about being caught. As is sometimes the case, though, the implications of Apple’s case are a little too complicated to allow for pure schaudenfreude

Fiona Apple has an incredible history, one that is well-known to both her fans and the music community in general. She began work on her first album, Tidal, at the age of seventeen and, in 1996, scored a major hit with the song “Criminal.” A chilling, rich, and sexually frank album, Tidal was a multi-platinum smash that provided Apple with the economic and artistic freedom to produce the (preposterously titled) album When the Pawn Hits the Conflicts He Thinks Like a King / What He Knows Throws the Blows When He Goes to the Fight / And He’ll Win the Whole Thing ‘fore He Enters the Ring / There’s No Body to Batter When Your Mind Is Your Might / So When You Go Solo, You Hold Your Own Hand / And Remember That Depth Is the Greatest of Heights / And if You Know Where You Stand, Then You Know Where to Land / And if You Fall It Won’t Matter, Cuz You’ll Know That You’re Right. Many critics argued that the album title alone showed Apple’s descent into the worst sort of faux-artistic pretension of popular music. Like so much about the singer’s life, however, the truth was a little more complicated.

Charges of Apple taking on John Lennon-esque levels of mugging pretension were ultimately misguided. Rather, all of Apple’s decisions – artistic and otherwise – seem to come from psychic scarring, a pain so deep that Alanis Morissette’s pronouncements on Jagged Little Pill seem trite by comparison. Over the years, Apple has admitted that she has spent much of her life struggling with depression and Obsessive Compulsive Disorder. One of her songs, “Sullen Girl,” was based on her experience getting raped at the age of 12 and subsequent years of psychotherapy. Even her ninety-word album title was a result of a personal crisis, as the understandably thin-skinned Apple, having read negative stories and letters about her work in Spin Magazine, broke down in tears and wailed “this can’t be happening!” Like so many artists, Apple’s work has come at an incalculable cost, one that has undoubtedly led her to self-destructive behavior.

Willie know what’s up.


This past Wednesday, Apple – who is now 35 – was stopped at the Border Patrol checkpoint in Sierra Blanca, Texas and searched for drugs. She had in her possession small amounts of marijuana and, more problematically, hashish. Possession of 0.01 pounds of hash is a felony in Texas and Apple – who admitted the drugs were hers – was booked at Hudspeth Couny Jail and then released a day later on a $10,000 bond. The arrest should come as no surprise, given that the same border patrol had previously busted Willie Nelson, Snoop Dogg, and Armie Hammer. Moreover, says Grantland’s Molly Lambert, Apple has a history of giving interviews in which she not only openly admits to self-medication with illegal drugs, but will do so in front of interviewers. If, by any chance, the staff of the Sierra Blanca border patrol included any fans of Rolling Stone, Apple could have expected a search and arrest.

Unsurprisingly, Apple’s arrest has resulted in a small but significant “Free Fiona” movement, the sort that arises when any celebrity (see: Simpson, O.J.) is charged with a crime. At the Huffington Post, Rosie Goldensohn makes the case that we are all Fiona Apple and that the singer is just another victim of the unjust War on Drugs that the staff of Points so often criticizes. Goldensohn points out that 1.6 million Americans were arrested for drug law violations in 2010, with 82% of the arrests being for possession. This is an undeniably damning statistic, but Goldensohn uses it as her entrée into the larger – and more problematic – argument that self-medication is a valid form of drug use. She claims “we are a nation of drug users, along with all our other coping mechanisms that counter the kind of personal pain Fiona articulates so openly” and, for that reason, Apple is no more a criminal a cutter, gambling addict, or compulsive overeater.

This is all your fault, hash.


This is a compelling argument, in that it rightly argues against the idea that drug users are villainous predators, diseased letches, or simple-minded deadheads. One can easily go too far on this front, however, claiming (as Goldensohn does) that there is no problem with marijuana, hashish, or self-medication. Such a view is untenably simplistic, so focused on rescuing Apple from condemnation that it makes a case against public health itself. No doctor with a lick of sense would encourage a patient to prescribe medications to themselves, particularly if those medications were not regulated for quality control and could easily be over-consumed. Such views are surprisingly common in “War on the War on Drugs,” however. Opponents of the U.S. Government’s senseless and anti-intellectual stance on drug use, sales, and distribution often engage in over-indulgent rhetoric of their own, arguing there are no issues with drug use and recreational drugs are an unmitigated good. In truth, there is a great deal to be said for moderation in the use of mood-altering substances, even if such a Ben Franklin-esque view tends to be unfashionable on both sides of the Drug War debate.

One need only look at Fiona Apple’s post-release concert in Houston on Friday night to see that the answer to the singer’s problems are not easier access to drugs. Seemingly buzzed on something, Apple opened up to the Space City crowd with a bizarre tangent about her experiences in the slammer:

Now, most of the people were very nice to me. There are four of you out there, and I want you to know that I heard everything you did. I wrote it all down with your names and everything you did and said stupidly thinking that I couldn’t hear or see you. I then ripped the paper up, but not before I encoded it and– I got two lock boxes. We’ll call them “holding cell one” and “holding cell two”. In “holding cell one” is the encoded version of the shit that you did that I know was inappropriate and probably illegal. In “holding cell two” is the decoder. I’m the only one who holds the key, and you and I will be intimate forever because I will hold that secret forever. Unless of course the celebrity that you had so much interest in but you wanted to accuse me of bringing up while you laughed at me all night? Unless you’re interested in being a celebrity, I’ll make you fucking famous any time you ask and I’ll open those boxes. So why don’t you stay in your fucking holding cell?

Miles Davis, at the age of 65, the last year of his life.


The lack of coherence in Apple’s speech is haunting, a testament not to her musical genius, but to the degrading effects of drug abuse. In popular culture, the image of the ‘tortured artist’ is so ubiquitous that we tend to celebrate the torture as much as the art, for we imagine the latter would not exist without the former. This is a terrible mistake, however. We should eagerly acknowledge that an artist like Fiona Apple (or Miles Davis or Amy Winehouse or whomever) would clearly have been better off without debilitating drug addictions. Put another way, to celebrate drug abuse and the subsequent degeneration of an artist’s mind and body because it facilitates the creation of great music is morally obscene.

In this vein, we must touch upon Apple’s 1997 MTV Video Music Award appearance, the single most infamous moment of Apple’s career. I remember watching Apple take the stage after winning the award for Best New Artist, seeing the strung-out singer, sallow eyes and slumped shoulders, murmur half-thought thoughts. She cryptically remarked that the “world is bullshit, and you shouldn’t model your life on what we think is cool, and what we’re wearing and what we’re saying” and “it’s just very stupid that I’m in this world.” Oddly, these comments have some resonance today. To a certain extent, in fact, Apple was right. She is a fine exemplar of the “bullshit” and “stupidity” of this world, being someone who represents the most irrational and tragic elements of the anti-War on Drugs movement. Better yet, perhaps she is a human Rorschach test, serving as an idol, an artist, a fool, or an ingrate in the eyes of most and, in the eyes of a small minority, a human being.

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