Why every mixtape needed a B-side

If you ever made a mixtape for someone, you know that the hardest decision was not the first song. It was the first song on side B. You had forty-five minutes on each side of a C90, and by the time you reached the end of side A you had said everything you meant to say. Side B was where you said the rest.

I have been thinking about this because streaming killed the flip. A playlist has no middle. It has no moment where the listener has to stand up, press eject, turn the tape over and decide to keep going. That moment was tiny, but it did a lot of work.

The architecture of a tape

People who made tapes seriously had rules. The first track on side A had to be something the listener already liked, so they would trust you. The last track on side A had to be the best song on the tape, so they would bother to flip it. And the first track on side B had to be a surprise.

That surprise is what I miss. It was usually the strangest song on the tape, the one you were least sure about. It was placed there on purpose, at a moment when the listener had already committed. They had turned the tape over. They were in. You could risk something.

Side A was the song you wanted them to hear. Side B was the song you wanted them to find.

Why the risk mattered

A mixtape was a letter in someone else’s words. On side A you were careful. You chose songs that said what you meant, but politely. On side B you were braver. The B-side was where the love song went, or the angry song, or the song you had listened to on repeat for a month without telling anyone.

The flip made that bravery possible because it created privacy inside the tape. If someone only listened to side A, they got the careful version of you. If they turned it over, they had chosen to hear the rest. It was consent, built into plastic.

The B-side in record history

Record labels knew this too. The B-side of a single was where bands hid the songs they loved but could not sell. Some of the best-known songs of the last sixty years started life on the back of something else, and only became famous because a radio DJ flipped the record out of boredom.

B-sides were allowed to be long, odd, quiet or unfinished. They carried no commercial weight, so they carried everything else. Fans who bought the single for the hit kept it for the song on the back.

Making a B-side in 2026

You can still build a flip into a playlist, even without plastic. I do it by making two playlists instead of one, and sending the second a day later, with no explanation. People who listen to the first and liked it will open the second. People who did not, will not. Either way, you have learned something.

• Side A: ten songs that say something true, politely.

• Side B: six songs that say it less politely, starting with the strangest.

• Send side B a day later, with no message. Let them choose to flip it.

The best mixtape I ever received had a single song on side B, followed by forty minutes of silence. I listened to all of it, waiting for more, and I still think about that silence more than any song. That is what a B-side is for. It is the part of the letter you write after you have run out of things you planned to say.