Just about everyone has that story about the first time they heard a certain album or song, how magical and perfect and transcendent it all was. I’ve always found the music that people can’t remember not hearing—that was simply always there—to be just as interesting. Three albums that were played so much in my pre-consciousness years that they are a part of my psyche come to mind: the Jesus Christ Superstar movie soundtrack, a cassette tape designed to teach children their times-tables through a song called Multiplication Unplugged, and Steely Dan’s Greatest Hits. It goes without saying that this early exposure to mathematics, the New Testament, and 1970s California jazz-rock has given me a tremendous advantage in everyday life.

These imprints were courtesy of my parents, and it speaks to a mixed approach that they had when it comes to what culture they saw as fit for their children. Stickin’ Around and Garfield were looked down on for their mutual fondness of the phrase “shut up” (long after we heard it every day at school), but Fawlty Towers and Saturday Night Live reruns, complete with various racial slurs, were fair game much earlier than expected. I didn’t know that “slut” was a bad word for years, because every year my Dad would play “Fairytale of New York” just after Disney’s Twelve Days of Christmas, and I had yet to hear it used outside of that song until I was a teenager. Representative of their more positive efforts were the rich supply of compilation albums on rotation in whatever Chevy van we had at the time.

There were the aforementioned greatest hits of Steely Dan, The Pogues,  Springsteen, Queen, The Clash, and others. Each confused me into believing something false about the band: Springsteen only got good in 1975 (an idea that my Dad was later happy to correct); Queen was a consistently good band (no other band benefits more from cherry-picking hits); but it was The Clash I was most misinformed about. First, the compilation in question was The Essential Clash, so I assumed that was their name, and people only called them The Clash for short. Second, the cover art of the band convinced me that the tough-looking blonde—Paul Simonon—was the snarling and screaming lead singer, Joe Strummer, not the visibly uncomfortable guy hiding behind him. Lastly, since this was a Father’s Day gift and we were a Catholic family, it had eight-year-old me believing that “White Riot” was acceptable music to play on the drive to church.

Looking back, I realize my generation was the beginning of the end for the “Greatest Hits” compilation. One of my earliest memories is looking at the cover of U2’s Best of 1980-1990 in a store and seeing a boy on the cover who sort of looked like me. For a while, I recalled wanting it and my dad acquiescing, but in reality I’d unknowingly been guided there by him and he had every intent on buying it. I fell for it hard, as it was my first exposure to rock, but by the time the follow-up for the next decade arrived in 2002, even I realized it was a case of diminishing returns.

Pre-internet, pre-vinyl-resurgence, and pre-iTunes, there was a need for collecting these tracks together on CD. You could have lost records and not been able to recover them, you could have heard a song long ago on the radio and just caught the artist’s name. Moreover, CDs provided a way to reconnect with the past without some of the past’s problems, not to mention an ideal conversation piece about what was truly the Best Of any given band. But soon these were overtaken by the Internet and the increasingly myriad ways one could connect to it and its infinite library. Just as it came of age, it showed its age. Walkmans were bulky next to MP3 players, CD collections were clutter once you imported the tracks to your iTunes, and to those who clung to vinyl, the trend of remastering specific albums saw the compilations’ audio quality outmatched. The murky audience for Best Ofs only stressed their coming reckoning—were they for nostalgic fans or for introducing new listeners? In turn, should they include deep cuts and rarities or stick to the hits? Was the chronology of releases worth preserving? How involved were the artists themselves?

As engaging as this debate may be to cosmopolitan and well-to-do audiophiles, not much of this was on my young mind. I lived far away from the places where music was made, concerts were staged, even where songs were sung about. There, people might have been able to argue such merits and drawbacks, but as a weird kid in Cape Breton who didn’t care much for Top 40, country, or the CBC (Vinyl Café excluded), I’d take what I could get. And as the youngest of four children, it was even less about what I wanted and more about what those older than me felt I was worth.

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My dad had one day brought OK Computer home; he didn’t buy much new music that wasn’t from Elvis Costello or Bruce Springsteen after that. My mom hated it and Donald, my oldest brother, loved it. He also loved the Barenaked Ladies, and finding and downloading the new track “Thanks That Was Fun” from their 2001 Greatest Hits was his first brush with piracy. While he was a precocious navigator of the early web, he suffered from a guilt-born habit of deleting any pirating software used on the family PC before our parents got home from work, which prevented him from discovering how to download full albums for a while. In those first years, he took in BNL, Radiohead, and Our Lady Peace bit by bit.

Using a variety of now-defunct services like ShareApe, Morpheus, and KaZaA, Donald was soon able to cobble together Amnesiac and other albums, eventually figuring out how to burn these onto CDs along with a few mixes of his own design. These mix tapes are best left unfound, but suffice to say there was Treble Charger. I understood basically none of his process until writing this article and asking him about it; I had simply accepted that by virtue of being five years older than me he could do stuff I couldn’t, as if long division and pulling music out of the ether were comparable skills. Despite the short lifespans of such methods in the 2000s, he always seemed able to adapt to the times while his tastes transitioned from North American alternative to British rock from the ‘60s onward.

My oldest sister, Maureen, went through a flurry of phases, alternately pushing Feist, The Smiths, and M.I.A., or anything she enjoyed from CBC Radio 2. As helpful as she was in expanding my horizons, it always seemed to come with some sense of hipness or sophistication that I could never aspire to. There was also a lingering influence of a series of CDs my mom would play for us called Women & Songs, which compiled a bunch of femininity and feelings and whisperiness that I couldn’t get my head around. As soon as I could understand it, I subscribed to the shitty adolescent boy ideology of “real music.” This junior high mentality has less to do with songs being about what was real, or even with production—given my loose grasp of how most of my favourite albums were made—and was more about being made by white males who were either old, broken up, or dead. Basically, no band still touring was worth listening to, unless Donald still thought they were cool, in which case they were. When you instinctively believe the past has no rival, it becomes very easy to think you’ve won arguments.

As time went on, four burgeoning musical personalities meant competition for the car stereo was becoming fierce, until Donald was gifted a CD player and speakers for his room. He and Maureen lived in the attic, while my other sister Clare, my parents, and I lived on the second floor. There was a hierarchy of coolness quickly solidifying. I can remember sitting as quietly as I could on the staircase landing leading up there, now unable to remember if I was hoping to absorb knowledge by osmosis or be invited up to prove I knew just as much as them. Donald and Maureen just thought it was creepy. Soon we each got our own CD Walkmans, which lent some sense of autonomy. Before I could develop an attachment, iPods hit. Maureen had an early MP3 player that could hold less than ten songs of poor quality. The iPod signalled a boundless new age, and as I entered junior high, I got a U2 Special Edition iPod in black with a red click wheel and the autographs of the band members engraved on the back. I promptly lost it at a track and field meet, and got another dubbed “Neil MaciPod” to last until the end of junior high, at which point Donald and Maureen both moved on to Halifax and Scotland, respectively, for university. It felt lonelier than I expected.

***

With my iPod and an increasing interest from my dad to fill in gaps in his CD collection fuelling my listening options, I thought I could finally see the big picture. The “real music” habit died hard, and it was time to seek greener pastures. As the internet began to morph into its current form, I figured out that there were issues of Rolling Stone aside from their “500 Greatest Whatever of All Time” fare, and that there was actually good music journalism beyond Rolling Stone. I began to follow my roots into bands that updated my old interests and introduced me to new concepts. Arcade Fire taught me, through Funeral, that an album could be “classic” despite being made after 1994.  Getting into Arctic Monkeys in 2008 showed me how it felt to jump on what I perceived to be a bandwagon and, in 2013, what it was like to see that bandwagon overrun. The Hold Steady were basically the Second Coming, largely because for the first time in my life I found a band that I later sold Donald on.

The older I got, the more meticulous I became in organizing my library. Regular disastrous library and organizational fuck-ups spawned by iTunes updates were weathered, sometimes deepening my interest as I could restructure my approach to the metadata from the ashes. All the artwork was as high-res as I could find, each album title had the year tacked onto the end in brackets, the album artist and artist fields were both filled, etc. Then came university and torrenting and streaming services and here we are. The replacement for Neil MaciPod (2007-2015, RIP) is a Touch, since the former died just after the Classic was discontinued. Frequent software updates, a reduced memory, and a seemingly-deliberate awfulness if you try to do anything but conform to the iCloud/syncing standard gets on my nerves. I try to find solace in vinyl like everyone else my age that wants to be cool, but it only does so much. Whenever faced with approaching a new artist, I tend to pirate a whole discography rather than a Greatest Hits collection, populating my library with a lot of music I mean to get to and really experience, y’know, but which I keep putting off.

A lot of this impulse traces back to habits developed in those early years. I still want to prove how much I know, so surely listening to everything an artist has ever done is the only way to do that? My blood boils when peers deride bands, especially those I grew up on, without having done their homework. This reacts and synthesizes with my now-life-dominating interest in history to motivate me toward the noble futility of trying to fully comprehend the past. I’m beginning to grasp how often those opinions I once held so close were reliant on my own ignorance, how each of my siblings were building their own relationships with music, and remembered a world before I came into it with living room dance parties. Those compilations of career highlights that I’ve come to see as manipulative and dishonest become more relatable as I try to tell my own story, and I feel more outmatched by the yawning cave of What I Don’t Know than I ever could have felt about my siblings’ knowledge.

On one occasion while driving with Clare, my previously unsung sister, I started playing OutKast from my iPod. She excitedly requested that I put on “Flip Flop Rock,” and proceeded to rap along almost perfectly, only losing Killer Mike and Big Boi at their most rapid and intricate lines. I was understandably taken aback, until she explained how she pressured mom into buying her Speakerboxxx/The Love Below on the mostly clean catchiness of “Hey Ya!” 12 years ago. A whole story—as long and self-indulgent as this one—could be written on the cultural earthquake Antwan Patton and André Benjamin must have brought into her world. And I’d only stumbled into it by attempting to show off my own sophistication.

The past is an incredible resource that we too often confine by drawing from it only what we want or what we feel is “real.” We can pine for what we once had endlessly without ever stepping back to view what was beyond us then, focused on winning arguments every generation starts, then fails to resolve. I started writing under the above lyric, thinking I’d reflect a bit on how some compilations succeeded and others failed. Maybe I’d write Best Of these Bests Of and sort out which were worthwhile. Maybe I’d reflect on how memory is like a Greatest Hits album, man. I now realize I was writing about albums of photos, not music. Images vivid and blurry, shaped by the ceaseless progress of time and technology, with a handful of memories I thought I knew yielding something new.