In celebration of Lou Ottens, the man who invented the cassette. Ottens passed away at 94, in the Netherlands, on March 6, 2021. RIP Lou~

My grandfather used to say, “If someone managed to express something you’re feeling with better eloquence, quote them.” However, at times words may bring an intimidating and awkward gravitas. It goes without saying that telling someone how you feel about them can be admittedly nerve-racking. This is where music comes in.

Though many of us grew up in an era in which mixtapes were ubiquitous, many a younger reader would likely be dumbfounded in attempting to even play one. It is, as they say, a lost art. By far, the best vessel for a mixtape has always been the one that started it all—the cassette. 

Just as my parent’s generation had to endure hipsters appropriating records on vinyl because it was retro, so now the cassette seems to be making an ironic comeback. 

Just as the crackling sound of vinyl on a record player carries its own reassuring warmth, there is a newfound romance to cassettes. The clickety-clack of it going into the tape player. The patience, or lack thereof, of not being able to rewind or fast forward quite to the spot you’re looking for. Forward, rewind, forward, rewind. The little plastic rectangle (I know, plastic bad. But not if it’s vintage plastic! Then it’s recycling!) Thus, the cassette still holds a fighting chance at a comeback. Here’s hoping. 

Now, while handing your sweetheart said cassette of that mix you worked away at all summer, so she wouldn’t forget you when she went back to school in the fall, was much more exciting than hitting the SHARE button on a playlist, we will keep this grounded in reality. Hence, this set of rules can be applied to any and all “platforms”— be it a CD (not quite retro enough to be cool again, but more user-friendly and can still be used in at least SOME cars) or Spotify, Apple, and so forth. 

As for the mix itself: like John Cuscak’s character in 2000’s High Fidelity put it, “The making of a good compilation tape is a very subtle art. Many do’s and don’ts. First of all you’re using someone else’s poetry to express how you feel. This is a delicate thing.”

And so, what we offer here is a set of such Do’s and Don’ts, of rules if you may, to nail the very subtle art of the mixtape.


This is the first rule, because it will inform much of what you’ll be doing on this mixtape. Too short and it will appear as though you didn’t bother putting in any effort. Too long and the person you’re making it for will drop off; the associated feeling of boredom now linked to your sentiment for them.

Old cassettes generally had two lengths—90 or 120 minutes. But often enough, most albums never went over 45 minutes. As a mixtape is essentially a great album of your feelings delivered via music, I would recommend you keep it under one hour.

Long songs can sometimes force you to break this last point. So long as you’re not adding a 20 minute behemoth on top of a heaping helping of radio hits, you’re good.

On average, this will mean something between 10 to 15 songs. You will find this hard to abide to at first. But just as a film is made in the editing room, so is a mixtape. Through cutting songs, you will start paying closer attention to the ones that actually reflect what you’re trying to say. Be as selective of your songs, as you are of your feelings. Or something like that. 


You’re making a mixtape for someone else. This means you should take into account their preferences in music. Say you just met them a few times  (if so, ballsy move with the mixtape, but I can appreciate a bold romantic gesture), and they were wearing a band t-shirt. You then proceed to create a mixtape based around that information, only to find out said t-shirt was borrowed (probably from an ex, but never mind that), and they’ve actually never heard of White Snake. Suddenly that ‘80s hard rock tape is gonna feel awkward.

In other words, ideally, you should know the person’s taste; this is the part where you have to learn to listen and not just talk. That one is probably a good dating rule in general, not just for mixtapes. But I digress. 

Figure out who they are (are they even worthy of your mixtaping efforts?) Inquire about their musical favorites. Who was the first artist they fell in love with? What band can’t they stand? Once you have those tidbits, you can better filter through your own collection of music, and pick the appropriate tracks.

When all else fails, throw a dart at a busy room and odds are that person will like Pop music.  


We’ve covered tailoring your song choices to the person you’re crafting this mixtape for. Now make sure your own taste is on display too. Compiling a mix of rap music when you’re secretly a giant country fan might not work for you. In other words, as in real life dating, be true to yourself. And don’t try to be cooler than you are. 

On the other hand, if you’re just a giant music snob who refuses to use any Top 40 music even though that is the only thing your mixtapee listens to, that also may not fly. Find the perfect balance between your taste and theirs.  


How many times have you listened to a song and thought it was about one topic, only to find out later on that it was about something vastly different?

Websites like often have annotations explaining what the songs mean and breaking down specific lines in the song. This should help you figure out if that one love song isn’t actually about a break-up… or just grossly inappropriate. Cut the songs that are dubious. 


Now that you’ve narrowed down the list, it’s time to figure out their order.

This will be laborious. Rome wasn’t built in a day, and neither will your mixtape. Generally speaking, the making of a good mix takes longer than you would think. But who said wooing was easy. You want to start out strong without giving up all of your best stuff up front. 

The first song should set the mood you’re trying to convey. Personally, I recommend at least three or four high energy ones, before bringing it down for the slow parts. You’ll likely want to save at least one big number for the last track. If you have a long song, the last spot in the tracklisting is often the best option.


Naming a mixtape is like naming an album. You can’t just call it Mixtape. You’ve poured your blood, sweat and tears into crafting it, don’t ruin it with an uninspired title.

Sometimes an event in your history with this person may inform the name. Fell in love walking in Central Park? (Hey, it worked for Robert Redford.) Name it, The Central Park Sessions.

You could use an inside joke, or a nickname you have for this person. If you’re absolutely imagination-less, you can’t go wrong with : Jane’s Mixtape vol.1.  (It goes without saying that replacing “Jane” with your mixtapee’s name is a must. ) “Vol. 1” has an old school feel, just like this gesture, and says: if all goes well, there could be more mixtapes in the lucky recipient’s future.


Presentation matters. If your mixtape is a Spotify playlist, upload a picture to match the sentiment. If you’re burning a CD or —indeed—making a cassette mix, print it out, or draw something yourself if you’ve got the skills. On physical media, don’t hesitate to write the tracklist on the booklet.  


You’ve completed your mixtape. You have over analyzed it and over listened to it, now your mixtape is ready to be handed off.

Keep it cool and remember: even if they don’t reciprocate the feeling, they’ll appreciate the effort. You’ve put yourself out there and explored your musical soul. And that will always be a positive thing. Now go express yourself and your feelings.


Death Row 30th Anniversary Cassette Reissue

Tape Head’s announced last week that they would be giving Dr. Dre, Snoop Dogg, and Tupac’s most seminal albums their very first cassette reissues in honor of Death Row’s 30th Anniversary. Available for Pre-Order now.

Cassette: A Documentary Mixtape

Cassette inventor Lou Ottens digs through his past to figure out why the format won’t die. Musicians like Henry Rollins and Thurston Moore join a new generation of bands releasing tapes to help Lou remember the importance of his creation.