The Lost Art of the Mix Tape


There are many reasons to make a music mix tape. To win the love of someone, to help a friend going through a rough patch or as soundtrack for a long road trip. Mix tapes require cassettes or CDs, something today’s youth view in the same realm as pay phones, typewriters and Tang. Streaming services like Spotify and Apple Music offer millions of songs just a click away. They’re doing what mix tapes used to do — introducing us to new music. But algorithms will never know us the way our friends do.

Mix tapes are not just a compilation of music but a baring of the soul. Done properly, a mix tape is like writing poetry. It reveals your deepest longings and vulnerabilities, the soft spots inside your heart. A mix tape is an MRI of your unconscious. It’s a portrait of who you are and how you view the world. It’s a way to connect with someone and communicate deep feelings through music.

Creating a mix tape takes hours of sweat and toil. You pore over each song compiling the perfect balance of melody, rhythm and lyrical content. A well-crafted mix tape steers clear of the obvious. If including a Jeff Buckley song, skip “Hallelujah” for something more obscure like “Satisfied Mind.” If opting for Dylan, forgo his early catalogue and choose a later gem like “Not Dark Yet.”

I’ve been making mix tapes all my life. As a teenager, I transferred vinyl to cassette. I sat on my floor surrounded by album covers, painstakingly studying each song until I found the perfect cut. Every mix tape had a title reflecting a specific theme. I played the tape over and over as I progressed, making sure each song flowed into the next toward an emotional crescendo.

I learned there are basic rules for making mix tapes. You need to identify your intention. Most of my early mix tapes were an attempt to win a woman’s heart. Authenticity matters. Instead of settling for a love song like “When a Man Loves a Woman” go for something more beguiling like the Yeah Yeah Yeahs “Maps” or “This Must Be the Place” by Talking Heads.

Avoid plagiarizing the love expressions of others. The film Ghost used the Righteous Brothers song “Unchained Melody” to express the love between Patrick Swayze and Demi Moore. This makes the song off limits as mix tape fodder. The same goes for movie love songs like “Shallow” (A Star is Born) and “Falling Slowly” (Once).

A mix tape should start strong and end strong. Like a relay race, you want to burst out of the gate with a compelling tune like “Teardrop” by Massive Attack. The mix should be an emotional journey with ups and downs, twists and turns. Spirited highs should blend with moments of contemplation. Select songs the listener has never heard to avoid associative baggage. The final song should leave the listener breathless like “How It Ends” by Devotchka.

Alternative songs are great but should be used with caution. I’m a huge fan of Neutral Milk Hotel but a song like “Two-Headed Boy” might scare someone away. If you include a songwriting depressive like Elliott Smith, go for an optimistic tune like “Happiness.” The Magnetic Fields’ “Book of Love” is beautiful but Stephin Merritt’s voice is bleak. Opt for a cover version like that sung by Robin Pecknold (of Fleet Foxes).

All good mix tapes include a meld of different genres, eras and languages. French is the most romantic language so love mix tapes should include something by Edith Piaf or Francoise Hardy. Choose at least one instrumental piece (early Brian Eno is great). Songs should reflect your personal taste. If you’re not into hip hop, don’t include hip hop. Avoid punk rock, death rock, opera and yodeling. Classical cuts are great but often don’t mix well with rock. Keep away from songs that use the theremin; they sound too much like a horror film.

Making a mix tape as a means of seduction is enthralling. Songs should express your sentimental side and show that you’re a true romantic. Demonstrate your empathy with a song like “Lean On Me” by Bill Withers. If your worldview is cynical be sure to show a hint of optimism with a song like “Wonderful” by My Morning Jacket.

Making a mix tape to save a troubled relationship is more challenging since the person knows you well and can smell your bullshit. Be earnest but don’t be maudlin. “Ain’t Too Proud To Beg” reeks of desperation. Go softer with something like “Let’s Stay Together” by Al Green. Express how much you miss someone by including songs that evoke shared memories. Emphasize your commitment to the relationship with a song like “2 Atoms in a Molecule” by Noah and the Whale. If you did something wrong, choose a song that says you’re sorry. If you really screwed up, spread apology songs throughout the mix.

If you need a secret weapon song to win someone back, try something by Snow Patrol. Or you might use “Throw Your Arms Around Me” by Hunters & Collectors or “I Will Follow You Into the Dark” by Death Cab For Cutie. Coldplay’s “Fix You” is an oft-chosen remedy for wounded relationships. Be wary here since the song is an anthem for dysfunction.

The worst mix tape is one you make after you’ve been dumped. In some ways it’s liberating since you have nothing to lose. This is the time to air grievances and expletives in the guise of music. Your ex doesn’t have to listen so use discretion. In most cases a person will succumb to curiosity and play the tape if only to affirm how much power they have over your feelings.

A good “I’ve been dumped” mix tape incorporates guilt and anger. For guilt, try something like “Terrible Love” by the National. For anger, include “Sabotage” by the Beastie Boys or something by the Violent Femmes. If you’re really pissed, go for CeeLo Green’s “F- -k you” though this scorched-earth tactic will obliterate any chance at reconciliation. Dark humor is preferable as expressed by Pearl Bailey in “I Need You Like I Need a Hole in the Head.”

After a breakup, it’s wise to make a mix tape for yourself. Include songs that express your inner pain. After a brutal breakup in my 20s, I made a mix tape I called “Splitsville” that included “Don’t Give Up” by Peter Gabriel and “How Can You Mend a Broken Heart” by the Bee Gees (corny but effective). Another song was “Why” by Annie Lennox because she sang the words, “How many times do I have to tell you I’m sorry for the things I’ve done?” This allowed me to scream, “Once, just tell me once.”

When I started dating again, I was reminded that mix tapes function as a compatibility tool. They help you determine if you’re with the right person. If you’re into Velvet Underground and your partner is listening to Dave Matthews, the relationship is doomed. One woman made me a Best of Jimmy Buffett mix tape. Needless to say, we never dated again.

When I met the woman who would become my wife, we made mix tapes for each other. I’ll never forget the first tape she gave me. It included artists I loved like the Pixies, This Mortal Coil and Nick Cave. It also included musicians I wasn’t familiar with like PJ Harvey and Low. She threw in an Ella Fitzgerald/Louis Armstrong classic and a song from the film The Moderns, one of my favorite soundtracks. By the time the 90-minute mix was over, I knew she was the woman for me.

The most important mix tape you’ll ever make is a mix for someone who is dying. I recently had this honor. My mom was in hospice and only had a few weeks to live. I visited her as much as possible. Knowing she spent her mornings and nights alone, I made her a mix tape.

I began with “Somewhere Over the Rainbow” by Israel Kamakawiwoʻole followed by Louis Armstrong’s “What a Wonderful World.” My mom was a big Barbra Streisand fan so I included “Memories.” I added Judy Garland’s “You’ll Never Walk Alone” and “Lullabye” by Billy Joel.

Every night when I said goodbye to my mom in her hospital bed, I cued the CD player to play the mix on repeat all night long. I hope I didn’t drive her crazy. I like to think the songs helped prepare her for her final journey. The final song was “In the Arms of an Angel” by Sarah McLachlan. It was a reminder to my mom to make herself “empty and weightless” as she prepared to “fly away from here.” The song culminated in the lyrics:

You’re in the arms of an angel. May you find some comfort here.

This was the last mix tape I ever made. I pray it brought my mom some peace.

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