How to Make the Perfect Mixtape in the Digital Age

Image via Complex Original

Making mixtapes has long been associated with sensitive music fanatics, largely of the male variety, painstakingly piecing together the sequence of songs that will tell that girl how he feels about her—perhaps feelings he’s yet to articulate in any direct way. And that (not entirely inaccurate) stereotype was cemented in pop culture by the 2000 film High Fidelity, and the Nick Hornby book upon which it was based. John Cusack’s character even lays out some of his rules for the making of a great compilation tape: “You gotta kick it off with a killer, to grab attention. Then you gotta take it up a notch, but you don’t wanna blow your wad, so then you gotta cool it off a notch. There are a lot of rules.” It’s hard to argue with that, but let’s just say that not every tape needs to open with a killer. You might want to ease in with something slow and seductive, or toss out something short and silly before things really get going. It doesn’t have to be representative of the whole, but it should lead the listener into a particular state, let them know whether the overall mood of the proceedings will be aggressive or soothing or playful.

Nobody makes a mixtape to make a completely cohesive whole. It’s patchwork by nature, which means that even if your overall aim is to have a set of music that fits together, at some point the seams will show. So you might as well let them show deliberately here or there. Follow a series of ballads with the raunchiest rap song you know, let a groove of danceable tracks collapse into a jagged post-punk song. In radio, disc jockeys are warned away from letting “trainwrecks” happen on the air that might annoy and put off audiences. But for an audience of one, whether it’s you or someone else, you can afford to take some chances and let some sounds clash for dramatic effect.

Now that the ability to store and transfer music is virtually limitless, there’s nothing stopping you from making a mixtape that’s 999 songs long. But time itself will stop you from listening to it, at least all in one sitting, and probably not more than once. And while you could theoretically just pile on songs and stop whenever you feel like it, there’s something valuable to be found in setting a time limit, however arbitrary, and sticking to it. The 90-minute cassette tape, the 80-minute compact disc, even a good old-fashioned hour; all of these are good round intervals of time in which you have room to stretch out and include a lot of great music without going into overkill. But even if you want to bust through those borders, it’s good to think of a piece of entertainment you might want to spend an evening with—a two-hour movie or a three-hour concert.

Continuing on the old media point: one of the reasons cassettes remain the classic mixtape format is because of the elegance of a two-sided recording. You get to the halfway point, and have the choice to either take a break or flip it over and start the second half. Either way, it’s a great organizing device to maintain in whatever medium you choose. If you have more than one song you’re dying to open with, don’t just throw them at Track 1 and Track 2; let the latter track open up the second side. Of course, if you’re filling an 80-minute CD, you could even go all out and think in terms of a double vinyl LP, with four 20-minute sides. Look to classic double albums for ideas on how to pace an 80-minute ride so that nothing feels like filler: Think of Prince’s Sign ’O’ The Times, where most of the hits were packed onto Side 3.

One thing that got lost in the transition from cassettes to discs and files—at least for a time—was the ability to edit. Making a pause tape, you could decide to use only part of a track if you wanted to, cutting off an unnecessary intro or the tedious hidden track at the end of a great closing track. And for years, it was unlikely that someone makings a CD-R or even an MP3 mix had the technical capabilities to alter a track from its original length. Now, there are all sorts of user-friendly options for audio editing, and dropping a track into GarageBand just to snip off an unwanted segment is one of those little ways you can go the extra mile to make a great compilation tape. Of course, you can get into more ambitious touches, fading an outro into an intro or looping a section, but at that point you’re starting to become an actual DJ, and that’s a whole other discipline.

A trainwreck here or there is fun, but for the most part, you want the transitions between tracks to feel right, to lend some kind of elegant logic to the idea of grabbing songs from here and there and throwing them together. Think about the last 10 seconds of a song, and what would be cool to hear in the first 10 seconds of the next song. Is there an odd, quiet little sound that would perk the listener’s ears up to catch something subtle in the next track? Is there a hard stop that would sound awesome going into a song that goes from 0 to 60? An album like A Tribe Called Quest’s The Low End Theory is a master class in transitions, the way every transition from one song to the next seems to fit together like a perfect puzzle piece. The beats don’t run together or overlap, but they seem to just click into place.

Hearing a song in the context of the album it was originally released on can permanently effect how you think of it. Some songs just sound like opening tracks and some sound like closers. But there’s something a bit lazy, or just boring, about using a song on a mixtape in the same place it originally appeared on the LP. Think of that great Track 9 that you always thought didn’t deserved to be buried in the back half of the album. Use that favorite closing track that feels like the end of a long journey as the end of your first side; it’ll help the second half feel like the beginning of a new chapter.

Making a mix for somebody else is ultimately a pretty indulgent act. But it doesn’t have to be a pompous “let me show you what good music is” ego trip. It can and should be a joyous, evangelical activity, sharing great songs and spreading your own love of music. Just don’t be the snobby “music expert” giving your mix recipient an “education.” If you were shocked they didn’t own a certain classic album, don’t lecture them—just open the mix with the song that proves its greatness. Dig in the crates for a track they might not know by an act they love, a worthy cover of their favorite song, or the song you just know they’d love if they heard it. You’re not going to make them happy all the time; odds are at least once or twice, they’re going to skip the track you thought was undeniable. But you’re not going to make a mix they enjoy unless that’s your number one priority. And if you’re making the mix for your own personal enjoyment, well, you’d be surprised how much you can annoy yourself with poor sequencing or pacing. The last thing you want is to feel the need to skip tracks on your own mix, so take care to make it something you’d actually enjoy.

Morphine’s Cure For Pain is one of my favorite albums, and I’ve always admired how it was (unintentionally) sequenced in a constant up-and-down rhythm. (Every even-numbered track is faster or more upbeat than the ones before and after it, and every odd-numbered track is slower or quieter than the ones before and after it.) Maintaining that kind of structure over the course of 20 or more tracks could get constrictive and even predictable, but keeping the approach in mind is helpful when you’ve got a mess of songs you love but no idea in what order they should run. Think of every slow song and giving breathing room between the bangers, and of every anthem giving the mix a shot in the arm in case the last ballad got things a little too sleepy. Or think of the energy of the songs coming in waves, working your way up to three or four big peaks over the course of the mix, much like a house DJ might. You don’t want to frontload the mix with all the fun energetic tracks, and stick the slowies at the end—it’ll feel like the air is slowly being let out of a balloon over the course of the mix, until it dribbles to a close.

Like any creative endeavor, mixtapes are an inexact science. All of these tips can help you, but you can’t be beholden to them. Break a rule when it feels right, or throw out rules entirely if you feel they don’t apply to your particular mix. There are all sorts of superstitions or formal traditions that you don’t need to be faithful to. These days, I avoid including more than one track by the same artist, but I used to do that all the time. Including two versions of the same song on a mix doesn’t appeal to me, but I could see a situation in which it would work great. There are a lot of rules, but John Cusack isn’t going to be looking over your shoulder enforcing them.