I still have this tangible token of her affection over 15 years later, and just played it last night. She wrote out the track list in her own handwriting in sharpie on the disc itself, with a little "To [Agnostic]" dedication and the date.
Most of the songs are deep cuts from indie groups of the late '90s and early 2000s, which was not the greatest period ever for music -- but that wasn't the point. I could've bought myself a compilation of garage-rock revival music if I had wanted something that resonated best with my tastes at the time. The point of a mixtape is to convey a gestalt message to the recipient, through a series of impressions.
It's only natural to search through contemporary songs for the intended lyrical content and emotional tone -- unless you're going for "remember our good ol' days" nostalgia after some time has passed. But we had just seen each other less than two years before, so the track list reflects that (the Flaming Lips, Bjork, Death Cab for Cutie, Belle and Sebastian). There actually are some older songs, but they're mostly contemporary renditions -- Aimee Mann's cover of "One" (is the loneliest number), the Sea and Cake's cover of "Sound and Vision", and the Delgados' cover of "Mr. Blue Sky". The one genuinely old song, "Kaze Wo Atsumete", was still contemporary in its own way for being featured on the Lost in Translation soundtrack.
Contemporary recordings make it more of a time capsule, so that when you open it later on, you'll be transported right back to the time of its creation. And not in order to re-live that cultural zeitgeist per se, but to feel once more the social and emotional connections you had back then with its maker, touched by their ghost across time.
* * *
That was from the tail-end of the CD's dominance as an audio medium, when mp3 files on a hard drive was becoming the new way to store music. The main source was mp3 files, and the blank CD was just there to receive them. This mirrored the pattern in the '90s, when the cassette was fading in relevance as the CD became the standard. At that time, the mixtape was a blank cassette that received music from the main source on a CD. Even before the rise of the CD, the original mixtape was a lower-quality blank, recorded onto using a sub-professional stereo system or boombox, and the source was a higher-quality official release from the record labels.
The common thread throughout that technological evolution is that the mixtape was not only DIY and personal, rather than professional and mass-produced, but using a somewhat antiquated format. At least, a format that felt like it was slipping out of our grasp, that we were deciding to let go of. It gave a wistful tone to the experience, like sending a handwritten letter instead of an email / text message / social media DM.
What would the next step in the progression look like in 2020, when mp3s stored offline on a hard drive are going the way of the dodo, replaced by online streaming services? Unfortunately, this is yet another fatal weakness of streaming vs. owning digital music (touched upon here). If you primarily listen to music by streaming, and you want to give those songs to someone else, you can't do it because you don't own them. You can't give them up to the recipient (like something physical), nor can you copy and transfer them (like information).
Please do not suggest "creating" a Spotify playlist and sharing the link with them. You might as well just text them the titles of the songs and say, "Find these on streaming when you get the chance, they're kind of amazing." You aren't giving them anything, since streaming does not confer ownership. While fine as a casual recommendation, as a gift it is impersonal, immaterial, and minimally thoughtful.
But this is not just a matter of tangible things bearing greater meaning than intangible concepts. It gets right down to the difference between renting vs. owning. Suppose you "created" a playlist of songs on YouTube, and sent them the link. At least for the time being, they can hear those songs in the order you chose, even if they don't own them. But then they return to the playlist a few years later, and all the videos have been taken down -- the uploader privated / deleted the video, the uploader deleted their entire account, the rights-holders locked the video out of the recipient's country, the rights-holders took down an unofficial upload, the rights-holders replaced one official upload with another one (say, with better audio/video quality, but now using a different URL from the one in the playlist), or any of a million other reasons.
All of a sudden, the playlist you "created" has been un-created by the streaming service, rendering it worthless on a functional level. All that's left is "the thought that counts" -- better than nothing, but something that will leave a bitter taste in the recipient's mouth, thanks to your choice of medium.
If you doubt this could happen, you've never clicked on a link from an old webpage (on the internet, "old" is 5 years or more). I experience this every time I look at an old blog post of mine -- the link sends you to a page that no longer exists, and possibly the entire site no longer exists. This is almost 100% when it's a link to an image file -- all gone, and only preserved if I saved the image to my hard drive and uploaded it myself to the blog when the post was originally composed.
Returning to the main point, almost no YouTube videos have survived that I'd linked to or embedded, whether they're of music or of people filming themselves goofing around. Some were recoverable, if the record label replaced one upload with another -- I could go back and edit the HTML code to point to the new, visible video. Generally, though, files that are streamed have a very brief lifespan. That's also why I write out the title and artist when embedding a video in a post now, despite that information being plainly visible in the video itself -- because in a few years, the video will be deleted, and the only trace of what I intended to convey will be the identifying text in my post.
* * *
And yet, all is not lost as long as we ditch the fake world of streaming and stay in, or return to, the real world of owning music. You can still buy mp3 files from iTunes and others, or rip them from a CD onto your hard drive, or dig them up from an old device that you still have lying around somewhere (whether you originally got them legally or not).
But how to store them on a medium that you will give to the recipient? You could go retro and burn them onto a CD, although you'd have to ask them if they have a device with an optical drive to play it. If not, send them a discman along with the CD (include batteries). You could pick one up at a thrift store for cheap, just test it first. (Bring batteries, and possibly headphones in case there aren't any at the store, then get a test disc from their CD section).
If they really like vintage stuff, and are special enough to be worth all the effort, you could make them a literal mixtape. Boomboxes with CD players and tape decks are a dime a dozen at thrift stores and Craigslist. High-quality blank cassettes can be bought on eBay. If the boombox also has an mp3 player, you might be able to dub them onto a tape. If not, burn the mp3s onto a CD, then play the CD in the boombox, and dub the playback onto a tape. You'd have to send them a tape player of some kind, too. Most walkmans by now have worn-out belts and won't play tapes, but you can buy refurbished ones with new belts on eBay.
However, I think the natural thing to do, at this point in the tech evolution, would be to transfer the mp3 files onto a good ol' mp3 player and give the whole package to them. To convey the slipping-away-ness of the storage medium, make it an mp3 flash player distinctly from the 2000s or early 2010s, not the handful of state-of-the-art ones that are still being made. Just make sure it's working and comes with any peripherals needed for playback and charging (e.g., 2nd-gen iPod Shuffle needs its dock, 3rd-gen needs earbuds with the player's control buttons on the cable).
The "newest" iPod Shuffles are still going for $40 on eBay, with older models around $15-25. The iPod Classic models go for a bit more if working, so not worth it for storing a mixtape, although perhaps worth it if you wanted to make a double-gift for a tech geek -- a nostalgic, functional iPod, and the mixtape. Avoid iPod Nanos, whose batteries bloat and compromise the screen. Non-Apple devices should be $10-15 for something decent.
With mp3 player hard drives of at least 1/2 GB, and up to 4 GB, you could easily load 10 separate mixtapes onto it if you wanted.
I don't think it would work to just give them a USB drive with the files loaded onto it, since they would just transfer the files to some other device that could play them, and then never come back to the physical token that you gave them. They should be reminded of you and your gift each time they play the songs. For that, you need to include them on a player, and only half-jokingly tell them to play them from that very device that you gifted them.
You're going to need to write some kind of note or card anyway, since you have no other way to leave them with your handwriting (unlike a cassette or CD, which you could write on directly, or on a liner sleeve). Something simple: a dedication, the date, the track list, and a reminder to listen on this device. They wouldn't see your writing every time they played it, unlike the cassette or CD, but only when they went through their memento box -- better than no writing at all, though.
* * *
Of course, this all assumes that kids these days -- or 20-somethings or 30-somethings -- have formed a close enough social-emotional bond with someone, to motivate them to commemorate that relationship with a personalized musical anthology. This was common for the last of the Gen X-ers like my college friend, but I'm less sure about the Millennials.
I'm certain they could find a current or old friend to make a playlist of songs for, and that they could get into the idea of using a CD or old mp3 player. They might not have difficulty doing the kind of mixtape which is simply a sampler of stuff you think they'd like but might not have heard yet. That is thoughtful and personalized, but not a commemoration and not conveying a larger message or impression to them.
Am I just prejudiced against a different generation? Well, when have Millennials made mixtapes for each other in any format? Again, with the purpose of making some kind of larger emotional point to the recipient, to cement a bond, not just give them a helpful sampler. The technical means have always been within their grasp -- illegally downloading mp3s, then burning onto a blank CD, and handing it or mailing it to the recipient. It's dead simple, and dirt cheap.
But did they ever do it? I've never heard them talk about the concept for their own experiences, although they may be aware of the practice among older generations. Perhaps it always has been and ever will be a Gen-X practice. Still, I think Boomers would have done it, too, if they had had the technical means available back in the '60s and '70s.
I think it does come down to Millennials and Gen Z-ers being raised entirely under helicopter parent norms, during a cocooning social mood, and under falling crime rates that make people feel safe enough to get by daily life on their own. All of those trends began circa 1990. It makes them uneasy opening up to others in a natural, sincere way. Those of us who grew up under latchkey kid norms, during an outgoing social mood, and under rising crime rates that made us rely on others, do not get paralyzed by anxiety at the thought of opening up to friends and acquaintances.
I'd be happy to be proven wrong about that, though, and it's never too late for the post-X generations to start sincere-posting IRL.