I can blame one among my earliest emotions of inadequacy on Apple founder Steve Jobs. It was an in any other case unremarkable elementary sleep-away journey, requiring a three-hour bus experience upstate. My then-best pal and I made a decision to take heed to Music and stare wistfully out of the window. Me, with a blue Walkman CD participant (a second-grade Christmas present accompanied by Avril Lavigne’s sophomore album Beneath My Pores and skin) and Paul Frank CD case (stuffed with a dozen Now That is What I Name Music collections). Her, with a brand-new iPod 3G. 

It was superior. It was cool. I used to be devastated. 

An hour later I used to be puking my guts out — half extreme automobile illness induced by studying too many friendship quizzes, half childhood vertigo on the realization that the occasions have been transferring on with out me. At this time, on the 20th anniversary of Apple opening the Itunes Music Retailer, the reminiscence sits in my thoughts as a generational marker, the start of my expertise in what was to be an upheaval in music discovery.

4 years after the journey, I had saved up the cash to purchase my first iPod, catalyzing a lifelong music obsession made stronger by the accessibility of digital music downloads. The one factor stopping me was the shortage of a checking account. As an alternative, I coveted the multicolored iTunes present playing cards, feverishly scanning birthday playing cards for the telltale pops of coloration (Inexperienced meant $15, orange meant $25, pink the uncommon $50… I by no means received a type of.) and doing the fast psychological math of how a lot faux music-buying cash I had gathered. I relished the Saturday afternoons I might spend on the household desktop, scrolling by the highest songs lists and buying total albums of songs if I used to be feeling notably jazzed. 

The day iTunes bumped up the person tune costs from $0.99 to $1.29 was the day I discovered that capitalism would by no means be on my facet. 

In pursuit of the Finest iTunes Library Identified To Man, I checked the shop each single day with a single mantra in thoughts: Be certain to obtain the Free Single of the Week. Earlier than I had discovered of music blogs and totally understood what websites like MySpace and Pandora Radio might provide (and even lengthy after), I used to be listening to these free songs. 

I can hint the evolution of my very own musical style alongside the whims of the iTunes Free Singles curators, and the large iTunes library I gathered naturally transitioned throughout units and thru every of my Apple eras. I received my first iPhone in highschool. My first Macbook senior 12 months of faculty. Apple Music the day it launched in 2015. AirPods in 2018. Saved Free Singles went with me by my private tech journey. 

Regardless that the iTunes buying platform might not be the trendsetter or Apple person favourite it as soon as was, it has been a notable affect on the tech big’s fashionable strikes. Past enterprise, the iTunes Music Retailer launched many to the thought of algorithmic curation. It was a intelligent transition away from CD-burning and private collections towards artwork dictated by the web, utilizing what I consider was Apple’s greatest function of all time: the iTunes Free Single of the Week. 

Reflecting on 20 years of the iTunes retailer, I painfully acknowledge how my life is inherently tied to Jobs’ most worthwhile mind little one. However as Apple — and the remainder of the fashionable world — has moved away from iTunes-style buying and as a substitute towards streaming, I am unable to assist however really feel that we do not give sufficient credit score to the best way the iTunes Music Retailer modified how millennial patrons envisioned their relationship to music consumption.    

Apple’s trailblazing ‘cool’ standing

One of the quintessentially fashionable moments of 2023 to date has been Eve Jobs saying she will’t dwell with out her iPhone. 

“It’s modified the best way we now have all lived our lives and, very merely put, my emotions on your complete factor is simply, it’s genius,” she told the New Yorker(opens in a new tab). As laughable because it was for a member of the Jobs clan to promote her household’s largest vendor as if it wasn’t the world’s most ubiquitous merchandise, she wasn’t technically wrong(opens in a new tab). iPhones modified how individuals conceptualized private units, accessed the web, took footage, even the methods we speak and textual content — and so they’ve remained the top-selling cellphone(opens in a new tab). 

The iPhone was a history-making addition to an already well-entrenched Apple ecosystem, one began lengthy earlier than with the introduction of Mac however which actually infiltrated the brains of millennials with the launch of the iTunes in 2001 and its second model, the iTunes Music Retailer, in 2003. 

The shop has shifted from a premier, Apple-only commerce platform to an antiquated one-stop store for Apple media. Designed as a revolutionary in-house approach to discover and buy music, it seamlessly built-in the Apple music expertise from an web web site to a PC-based media library and again, which constructed off of the awe-inducing storage capability of early iPods.

The Free Single as ‘risk-free’ discovery

As early as one 12 months into Apple’s digital audio file buying enterprise, the corporate was already claiming it had revolutionized the tumultuous music {industry}, stepping over the cooling embers of Napster’s illegal peer-to-peer file sharing(opens in a new tab) demise. 

In a press release from 2004(opens in a new tab), Apple claimed its “99 cents-per-song pricing, free previews, one-click buying and downloading, and groundbreaking private use rights” have been the brand new frontier of authorized music file sharing, notching a “greater than 70 p.c market share of authorized downloads for singles and albums.”

The corporate unveiled it was releasing the third technology of its retailer — the up to date model of an iTunes with buying talents — and increasing its library of songs to 700,000. (Think about trying 18 years into the longer term and seeing Apple Music reach the 100 million songs milestone(opens in a new tab) in 2022.) 

Apple additionally introduced within the 2004 launch that iTunes can be launching a brand new “iMix” function, a means for customers to publish playlists of their favourite songs for others to see and even buy, meant to create “a digital iTunes group.” There was additionally a singular “Celebration Shuffle” playlist, letting customers select and queue songs from their library like their very own private DJ — sound acquainted?

One final particular shock: iTunes would offer free music to its customers each week. Cool, albeit a crumb of the free music repositories listeners used to entry with unlawful websites.

“The unbeatable mixture of iTunes and the market-leading iPod provides music followers a seamless expertise for locating, shopping for, managing and having fun with their music anyplace,” wrote Jobs within the 2004 announcement. The shop can be “spotlighting rising artists and providing iTunes prospects a risk-free approach to uncover new music.”

The brand new options have been providing authorized alternate options to frowned-upon teen “hacker” habits, and introducing the notion of discoverability to the purchasing web site. The iMix and Celebration Shuffle options have been in some ways the inspiration of what would later construct social- and peer-based streaming platforms like Spotify, adopted shortly thereafter by Apple Music.

For youthful customers like me, iTunes had picked up the place different websites had floundered, emphasizing our want for fashionable discovery. Later, different websites like Pandora Radio’s listening app, the aesthetically curated playlists of 8Tracks(opens in a new tab), and finally Spotify would hone in on discoverability and curation, however none of them supplied the flexibility to personal the brand new music we listeners have been each organically and inorganically discovering. 

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It felt just like the Free Single, specifically, was the arbiter of “I listened to them first” snobbery, with the shop highlighting up-and-coming artists that will typically go on to dominate the charts. As a younger music listener with a change allowance, an iPod Contact, and a dream, these singles have been additionally essentially the most accessible, and truest, barometer for “Good Music” I had.

The success of the preliminary Free Single launch later led to its growth, providing genre-specific singles (nation, hip-hop), free music movies, and even free TV episodes, films, and paid app downloads. In 2009, the shop additionally launched a “12 Days of Christmas” annual giveaway(opens in a new tab), providing each day packages of free media downloads in the course of the vacation season.   

As Apple’s choices grew and the shop aged, “feeler” singles from industry-touted hopefuls have been nonetheless occupying the free spot and chronicled the rise of 2010s music style. 

In September 2012, “Amsterdam” from a brand new band known as Think about Dragons received the function. The band’s mega-hit “Radioactive” can be launched one month later. Kacey Musgraves’ “Blowin’ Smoke” was highlighted in 2013, the second single from her Grammy-winning debut album. “Ribs(opens in a new tab)” by Lorde received the therapy in 2013, sizzling on the success of her hit “Royals.” 

Tumblr-era indie listeners would possibly recall the impression of Free Singles like “Youth” by Daughter, “Chocolate” by The 1975, “24 Hours” by Sky Ferreira, or “The Wire” by Grammy-nominated HAIM. 

The Free Single spot was primarily used for each social and {industry} clout. In 2009, following greater than 650,000 Free Single downloads of the song “Fireflies”(opens in a new tab), the band Owl Metropolis satisfied their label to push an early bodily launch for his or her debut album. Comparable tales might be discovered throughout genres, like various rock band Cage The Elephant’s “Ain’t No Relaxation for the Depraved” and singer-songwriter (and now-Broadway star) Sara Bareilles’ “Love Music”, which was launched as a Free Single three days earlier than it went to market. 

One other standout? “The A Workforce” by an ascending Ed Sheeran, featured because the Free Single on June 14, 2012. 

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A type of older sister of TikTok’s new hit-making power(opens in a new tab), iTunes’ Free Single program might be in charge for many of these mid-2000s earworms nonetheless blaring over your driving playlists in the present day. 

Sadly, no official repository exists for each Free Single launched over the initiative’s 12 years, though old music blogs(opens in a new tab), forums(opens in a new tab), and recent Reddit threads(opens in a new tab) have archived most of the choices. Customers on Twitter have documented their favourite Free Singles over time, too, a cyclical meme of “Who else remembers?” posts highlighting their most outlandish finds courtesy of the iTunes retailer.
 

Again in 2004, Jobs quoted the toddler retailer’s standout artists because the Foo Fighters, Avril Lavigne, Courtney Love, Annie Lennox, Jane’s Dependancy, Counting Crows, Renee Fleming, and Nelly Furtado. He heralded iTunes’ possession of the coveted Motown label archive, hinting at an older demographic of Apple listeners. 

However the enduring legacy of the iTunes retailer is not in solidifying the careers of already profitable {industry} stars, though fandoms worldwide(opens in a new tab) are nonetheless manipulating the iTunes charts to just do that. It is in sowing a seed of discoverability because the penultimate objective of a digital music listener, of constructing a group of songs by intangible information solely — and solidifying an {industry} actuality that sufficient digital downloads might warrant a radio and cultural takeover, lengthy earlier than a bodily album is even launched. 

In 2015, forward of the launch of Apple Music, the Free Single program took its final breath. It was known as a “relic of a bygone music-consumption era(opens in a new tab)” by media retailers reporting the information, with songs that “collected mud” in customers’ libraries. Apple had held on to it longer than most others, however it was time to embrace the subsequent massive factor. 

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iTunes’ world domination and an all-encompassing ecosystem 

A 2006 survey(opens in a new tab) performed by world market analysis agency Ipsos, a part of its “TEMPO: Holding Tempo With Digital Music Conduct” report, discovered that one in 5 Individuals over age 12 owned at the least one transportable MP3 participant. Virtually half (44 p.c) of the gamers’ music libraries got here from the proprietor’s private CD assortment, 6 p.c from others’ CD collections, 25 p.c from fee-based downloads, and 19 p.c from file-sharing companies.

The report’s creator, Matt Kleinschmit, wrote that the “findings exhibiting the need for broader multimedia content material on a conveyable gadget might counsel we’re reaching a turning level wherein customers are really recognizing the worth of anytime, anyplace multimedia content material on-the-go.” A separate survey of college students(opens in a new tab) by analysis group Student Monitor(opens in a new tab) reported that iPods have been the primary most “in” merchandise, surpassing “beer” within the prime spot for the primary time because the web beat it out quickly in 1997. 

Simply as rapidly because the iPod and iTunes have been launched to the road of Apple merchandise, customers have been already committing to the corporate’s singular compatibility. Schools and universities within the early 2000s, responding to the rise of unlawful file downloads, started providing free entry to file sharing websites (even post-lawsuit Napster(opens in a new tab)) with a view to cut back piracy claims and bandwidth use. However, in keeping with a 2006 report by eSchool Information, faculty college students merely weren’t utilizing the websites anymore, with some pupil councils outright dismissing them, as a result of they weren’t appropriate with the newest MP3 craze. 

“Purdue College officers say lower-than-expected demand amongst its college students stems partially from all of the irritating restrictions that accompany authorized downloading,” eSchool Information reported. “There’s additionally the issue of compatibility: The companies will not run on Apple computer systems, that are owned by 19 p.c of faculty college students… As well as, the information will not play on Apple iPods, that are owned by 42 p.c of faculty college students.”

Combining each the software program and {hardware} of the tech’s most coveted leisure actions below a single Apple umbrella — after which incentivizing prospects to remain throughout the ecosystem by options just like the Free Single of the Week — dedicated practically a whole technology to the model. 

It additionally disrupted an {industry} dominated by bodily media, one that will later make an much more dramatic shift in the direction of streaming subscription fashions.

“There isn’t that a lot we will do,” stated Aileen Atkins, Napster’s senior vp for enterprise affairs and basic counsel, to eSchool Information on the time. “If [students] have an iPod, they’ll purchase it on iTunes. It is a reality of life.”

A convergence of pocket tech, World Vast Internet accessibility, and the rise of widespread social media platform use concentrated a technology of latest artists, collectors, and listeners right into a distinctly digital market, to be wrapped right into a music {industry} reckoning that was adjusting to the ability and unpredictability of the web. 

At this time, speaking about formative iTunes experiences is a collective train in nostalgia and a mirrored image on the dizzying velocity of Apple’s technological evolution. It is also a prescient reminder of how the music {industry} has subtly dictated our particular person tastes, reconstructed tech’s position within the creation of artwork, and ushered within the lack of private use rights and possession by streaming, over only a single decade. 

“At Apple Music, human curation has at all times been the core to all the pieces we do,” wrote Apple’s world head of editorial Rachel Newman within the 2022 Apple Music announcement, “each in methods you possibly can see, like our editorial playlists, and methods you possibly can’t, just like the human contact that drives our advice algorithms.” 

As Apple digs its heels deeper into the custom of human curation, different giants are dipping a toe in Artificial Intelligence, utilizing it of their mission to be tastemakers and within the means of making the music itself.

Music discovery is a completely totally different recreation in the present day, with the influences of mainstream social media influencing, TikTok soundbites going totally viral, and algorithm-based playlists filling the invention hole left by the iTunes Free Single of the Week. Twenty years in the past, it was a novelty to have the ability to buy, obtain, retailer, and play information on a single transportable gadget — to get that totally free was an thrilling deal with, effectively well worth the time, power, or occasional sweepstakes entry(opens in a new tab).

It is practically inconceivable to think about what the playlists of the longer term will appear like as know-how’s automated grip tightens on music discovery. However digital remnants of the iTunes Music Retailer’s beginnings, discovered it within the forgotten Free Singles sitting on the backside of your iTunes’ bought folder, provide a nostalgic time capsule of how we have arrived right here, with the world’s musical catalog at our fingertips.