I can gay grandpa sex videosblame one of my earliest feelings of inadequacy on Apple founder Steve Jobs. It was an otherwise unremarkable elementary sleep-away trip, requiring a three-hour bus ride upstate. My then-best friend and I decided to listen to music and stare wistfully out of the window. Me, with a blue Walkman CD player (a second-grade Christmas gift accompanied by Avril Lavigne's sophomore album Under My Skin) and Paul Frank CD case (filled with a dozen Now That's What I Call Musiccollections). Her, with a brand-new iPod 3G.
It was advanced. It was cool. I was devastated.
An hour later I was puking my guts out — part severe car sickness induced by reading too many friendship quizzes, part childhood vertigo at the realization that the times were moving on without me. Today, on the twentieth anniversary of Apple opening the iTunes Music Store, the memory sits in my mind as a generational marker, the beginning of my experience in what was to be an upheaval in music discovery.
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Four years after the trip, I had saved up the money to buy my first iPod, catalyzing a lifelong music obsession made stronger by the accessibility of digital music downloads. The only thing stopping me was the lack of a checking account. Instead, I coveted the multicolored iTunes gift cards, feverishly scanning birthday cards for the telltale pops of color (Green meant $15, orange meant $25, pink the rare $50… I never got one of those.) and doing the quick mental math of how much fake music-buying money I had accumulated. I relished the Saturday afternoons I'd spend on the family desktop, scrolling through the top songs lists and purchasing entire albums of songs if I was feeling particularly jazzed.
The day iTunes bumped up the individual song prices from $0.99 to $1.29 was the day I learned that capitalism would never be on my side.
A 2003 advertisement for iTunes' $0.99 songs. Credit: Justin Sullivan /Getty Images In pursuit of the Best iTunes Library Known To Man, I checked the store every single day with a single mantra in mind: Make sure to download the Free Single of the Week. Before I had learned of music blogs and fully understood what sites like MySpace and Pandora Radio could offer (and even long after), I was listening to those free songs.
I can trace the evolution of my own musical taste alongside the whims of the iTunes Free Singles curators, and the massive iTunes library I accumulated naturally transitioned across devices and through each of my Apple eras. I got my first iPhone in high school. My first Macbook senior year of college. Apple Music the day it launched in 2015. AirPods in 2018. Saved Free Singles went with me through my personal tech journey.
iTunes gift cards were an elite birthday gift in 2008. Credit: Justin Sullivan / Getty Images Even though the iTunes purchasing platform may no longer be the trendsetter or Apple user favorite it once was, it has been a notable influence on the tech giant's modern moves. Beyond business, the iTunes Music Store introduced many to the idea of algorithmic curation. It was a clever transition away from CD-burning and personal collections toward art dictated by the internet, using what I believe was Apple's best feature of all time: the iTunes Free Single of the Week.
Reflecting on 20 years of the iTunes store, I painfully acknowledge how my life is inherently tied to Jobs' most profitable brain child. But as Apple — and the rest of the modern world — has moved away from iTunes-style purchasing and instead toward streaming, I can't help but feel that we don't give enough credit to the way the iTunes Music Store changed how millennial patrons envisioned their relationship to music consumption.
Apple's trailblazing 'cool' status
One of the most quintessentially modern moments of 2023 so far has been Eve Jobs saying she can't live without her iPhone.
"It’s changed the way we have all lived our lives and, very simply put, my feelings on the entire thing is just, it’s genius," she told the New Yorker. As laughable as it was for a member of the Jobs clan to advertise her family's biggest seller as if it wasn't the world's most ubiquitous item, she wasn't technically wrong. iPhones changed how people conceptualized personal devices, accessed the internet, took pictures, even the ways we talk and text — and they've remained the top-selling cellphone.
The iPhone was a history-making addition to an already well-entrenched Apple ecosystem, one started long before with the introduction of Mac but which really infiltrated the brains of millennials with the launch of the iTunes in 2001 and its second version, the iTunes Music Store, in 2003.
The store has shifted from a premier, Apple-only commerce platform to an antiquated one-stop shop for Apple media. Designed as a revolutionary in-house way to find and purchase music, it seamlessly integrated the Apple music experience from an internet site to a PC-based media library and back, which built off of the awe-inducing storage capacity of early iPods.
The Free Single as 'risk-free' discovery
As early as one year into Apple's digital audio file purchasing venture, the company was already claiming it had revolutionized the tumultuous music industry, stepping over the cooling embers of Napster's illegal peer-to-peer file sharingdemise.
In a press release from 2004, Apple claimed its "99 cents-per-song pricing, free previews, one-click purchasing and downloading, and groundbreaking personal use rights" were the new frontier of legal music file sharing, notching a "more than 70 percent market share of legal downloads for singles and albums."
The company unveiled it was releasing the third generation of its store — the updated version of an iTunes with purchasing abilities — and expanding its library of songs to 700,000. (Imagine looking 18 years into the future and seeing Apple Music reach the 100 million songs milestonein 2022.)
The initial version of iTunes was launched in 2001, as a way for iPod users to manage personal music files. Credit: Kim Kulish / Corbis via Getty Images Apple also announced in the 2004 release that iTunes would be launching a new “iMix” feature, a way for users to publish playlists of their favorite songs for others to see and even purchase, intended to create "a virtual iTunes community." There was also a unique "Party Shuffle" playlist, letting users choose and queue songs from their library like their own personal DJ — sound familiar?
One last special surprise: iTunes would be offering free music to its users every week. Cool, albeit a crumb of the free music repositories listeners used to access with illegal sites.
“The unbeatable combination of iTunes and the market-leading iPod offers music fans a seamless experience for discovering, buying, managing and enjoying their music anywhere,” wrote Jobs in the 2004 announcement. The store would be "spotlighting emerging artists and offering iTunes customers a risk-free way to discover new music."
Apple CEO Steve Jobs announces the launch of the "iTunes Music Store" in Great Britain, Germany, and France in 2004. Credit: Ian Waldie / Getty Images
The new features were offering legal alternatives to frowned-upon teen "hacker" behavior, and introducing the notion of discoverability to the shopping site. The iMix and Party Shuffle features were in many ways the foundation of what would later build social- and peer-based streaming platforms like Spotify, followed shortly thereafter by Apple Music.
For younger users like me, iTunes had picked up where other sites had floundered, emphasizing our desire for trendy discovery. Later, other sites like Pandora Radio's listening app, the aesthetically curated playlists of 8Tracks, and eventually Spotify would hone in on discoverability and curation, but none of them offered the ability to own the new music we listeners were both organically and inorganically finding.
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It felt like the Free Single, in particular, was the arbiter of "I listened to them first" snobbery, with the store highlighting up-and-coming artists that would often go on to dominate the charts. As a young music listener with a change allowance, an iPod Touch, and a dream, those singles were also the most accessible, and truest, barometer for “Good Music” I had.
The success of the initial Free Single launch later led to its expansion, offering genre-specific singles (country, hip-hop), free music videos, and even free TV episodes, movies, and paid app downloads. In 2009, the store also launched a "12 Days of Christmas" annual giveaway, offering daily packages of free media downloads during the holiday season.
As Apple's offerings grew and the store aged, "feeler" singles from industry-touted hopefuls were still occupying the free spot and chronicled the rise of 2010s music taste.
In September 2012, "Amsterdam" from a new band called Imagine Dragons got the feature. The band's mega-hit "Radioactive" would be released one month later. Kacey Musgraves' "Blowin' Smoke" was highlighted in 2013, the second single from her Grammy-winning debut album. "Ribs" by Lorde got the treatment in 2013, hot on the success of her hit "Royals."
Free singles were bestowed with a special banner at the bottom of its album artwork. Credit: Chase DiBenedetto / Apple 
A relic of times past from the writer's music library. Credit: Chase DiBenedetto / Apple Tumblr-era indie listeners might recall the impact 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 essentially used for both social and industry clout. In 2009, following more than 650,000 Free Single downloads of the song "Fireflies", the band Owl City convinced their label to push an early physical release for their debut album. Similar stories can be found across genres, like alternative rock band Cage The Elephant's "Ain't No Rest for the Wicked" and singer-songwriter (and now-Broadway star) Sara Bareilles' "Love Song", which was released as a Free Single three days before it went to market.
Another standout? "The A Team" by an ascending Ed Sheeran, featured as the Free Single on June 14, 2012.
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A kind of older sister of TikTok's new hit-making power, iTunes' Free Single program is probably to blame for most of those mid-2000s earworms still blaring over your driving playlists today.
Unfortunately, no official repository exists for every Free Single released over the initiative's 12 years, although old music blogs, forums, and recent Reddit threadshave archived many of the offerings. Users on Twitter have documented their favorite Free Singles over the years, too, a cyclical meme of "Who else remembers?" posts highlighting their most outlandish finds courtesy of the iTunes store.
Back in 2004, Jobs quoted the infant store's standout artists as the Foo Fighters, Avril Lavigne, Courtney Love, Annie Lennox, Jane's Addiction, Counting Crows, Renee Fleming, and Nelly Furtado. He heralded iTunes' ownership of the coveted Motown label archive, hinting at an older demographic of Apple listeners.
But the enduring legacy of the iTunes store isn't in solidifying the careers of already successful industry stars, although fandoms worldwideare still manipulating the iTunes charts to do just that. It's in sowing a seed of discoverability as the penultimate goal of a digital music listener, of building a collection of songs through intangible files only — and solidifying an industry reality that enough digital downloads could warrant a radio and cultural takeover, long before a physical album is even released.
In 2015, ahead of the launch of Apple Music, the Free Single program took its last breath. It was called a "relic of a bygone music-consumption era" by media outlets reporting the news, with songs that "collected dust" in users' libraries. Apple had hung on to it longer than most others, but it was time to embrace the next big thing.
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iTunes' world domination and an all-encompassing ecosystem
A 2006 surveyconducted by global market research firm Ipsos, part of its "TEMPO: Keeping Pace With Digital Music Behavior" report, found that one in five Americans over age 12 owned at least one portable MP3 player. Almost half (44 percent) of the players' music libraries came from the owner's personal CD collection, 6 percent from others' CD collections, 25 percent from fee-based downloads, and 19 percent from file-sharing services.
The report's author, Matt Kleinschmit, wrote that the "findings showing the desire for broader multimedia content on a portable device could suggest we are reaching a turning point in which consumers are truly recognizing the value of anytime, anywhere multimedia content on-the-go." A separate survey of college studentsby research group Student Monitorreported that iPods were the number one most "in" item, surpassing "beer" in the top spot for the first time since the internet beat it out temporarily in 1997.
Just as quickly as the iPod and iTunes were introduced to the line of Apple products, users were already committing to the company's singular compatibility. Colleges and universities in the early 2000s, responding to the rise of illegal file downloads, began offering free access to file sharing sites (even post-lawsuit Napster) in order to reduce piracy claims and bandwidth use. But, according to a 2006 report by eSchool News, college students simply weren't using the sites anymore, with some student councils outright dismissing them, because they weren't compatible with the latest MP3 craze.
iTunes wasn't just for Mac users. Credit: Des Jenson / Bloomberg via Getty Images "Purdue University officials say lower-than-expected demand among its students stems in part from all the frustrating restrictions that accompany legal downloading," eSchool News reported. "There's also the problem of compatibility: The services won't run on Apple computers, which are owned by 19 percent of college students… In addition, the files won't play on Apple iPods, which are owned by 42 percent of college students."
Combining both the software and hardware of the tech's most coveted leisure activities under a single Apple umbrella — and then incentivizing customers to stay within the ecosystem through features like the Free Single of the Week — committed nearly an entire generation to the brand.
It also disrupted an industry dominated by physical media, one that would later make an even more dramatic shift towards streaming subscription models.
"There isn’t that much we can do," said Aileen Atkins, Napster's senior vice president for business affairs and general counsel, to eSchool News at the time. "If [students] have an iPod, they're going to buy it on iTunes. It's a fact of life."
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Today, talking about formative iTunes experiences is a collective exercise in nostalgia and a reflection on the dizzying speed of Apple's technological evolution. It's also a prescient reminder of how the music industry has subtly dictated our individual tastes, reconstructed tech's role in the creation of art, and ushered in the loss of personal use rights and ownership through streaming, over just a single decade.
"At Apple Music, human curation has always been the core to everything we do," wrote Apple's global head of editorial Rachel Newman in the 2022 Apple Music announcement, "both in ways you can see, like our editorial playlists, and ways you can’t, like the human touch that drives our recommendation algorithms."
As Apple digs its heels deeper into the tradition of human curation, other giants are dipping a toe in Artificial Intelligence, using it in their mission to be tastemakers and in the process of making the music itself.
Music discovery is an entirely different game today, with the influences of mainstream social media influencing, TikTok soundbites going fully viral, and algorithm-based playlists filling the discovery gap left by the iTunes Free Single of the Week. Twenty years ago, it was a novelty to be able to purchase, download, store, and play files on a single portable device — to get that for free was an exciting treat, well worth the time, energy, or occasional sweepstakes entry.
It's nearly impossible to imagine what the playlists of the future will look like as technology's automated grip tightens on music discovery. But digital remnants of the iTunes Music Store's beginnings, found it in the forgotten Free Singles sitting at the bottom of your iTunes' purchased folder, offer a nostalgic time capsule of how we've arrived here, with the world's musical catalog at our fingertips.