June 1999: C-90 cassette tape.

1. Cowboy Junkies, "Something More Besides You"
2. Sam Phillips, "Plastic is Forever"
3. XTC, "I'd Like That"
4. Morcheeba, "Part of the Process"
5. Ani DiFranco, "Everest"
6. Saint Etienne, "Former Lover"
7. New Order, "Temptation"
8. Velvet Underground and Nico, "I'll Be Your Mirror"
9. Concrete Blonde, "Someday?"
10. Billy Bragg and Wilco, "California Stars"
11. Belle and Sebastian, "A Summer Wasting"
12. Meryn Cadell, "Maidenform"

1. Bjork, "Joga"
2. Portishead, "Glory Box"
3. Jane Siberry, "Would You Go"
4. Joni Mitchell, "The Arrangement"
5. R.E.M., "At Your Most Beautiful"
6. Rufus Wainwright, "April Fools"
7. Soul Coughing, "Is Chicago, Is Not Chicago"
8. Serge Gainsbourg and Jane Birkin, "Je T'Aime... Moi Non Plus"
9. Towa Tei, "Obrigado"
10. Dead Can Dance, "Emmeleia"
11. PJ Harvey, "Is This Desire"

The first mix you make for someone, of course, is the most crucial one. You want to expose them to all the music that means something to you, but you also want to make sure it's stuff you can imagine them liking, based on what you know about them, or what they have in their collection.

This was the first of many mixtapes I made for M. A former roommate (she moved out partially 'cause she couldn't stand the third person we lived with), she eventually ended up out West and is currently a law student. Once upon a time in Boston, however, she was an aspiring musician/artist/waitress/writer/actress (I don't think I've left anything out.) Like me, she was never a serious musician, but loved music passionately. When we first met, she confessed to having a poster of Michael Hutchence on her bedroom wall when she was a teen, and once told me the only person she ever wrote a fan letter to was Sheryl Crow.

For her 25th birthday, I made her two mixtapes: this one (the title is meaningless, just a clever grocery list culled from track titles) and another called MOOD SWINGS, which wasn't radically different in tone or selection; I simply had too many good songs for one tape. She raved about MOOD SWINGS more, although, in my opinion, this one was slightly better. I'd been making mixes for about five years by this time, and I think I was really beginning to get the hang of setting a mood. The Cowboy Junkies song that kicks off side one also kicks off my favorite album of theirs, LAY IT DOWN (1996). When I made this mix, I'd just heard the song in the film NIAGARA, NIAGARA, where it also had an indelible, establishing effect.

I was also learning how to make interesting, carefully orchestrated transitions between tracks: one of my faves is Bjork lost in a heavenly echo chamber, repeating the proclamation, "state of emergency / is where I want to be" over and over until it gives way to the ever-so-gradual fade in of the Issac Hayes string sample on Portishead's cinematic, devastating "Glory Box". I also aimed for far more dramatic side-closers than ever before, searching for haunted spaces in a capella songs by Meryn Cadell, Dead Can Dance, and, with her guitar, PJ Harvey.

Most non-thematic mixes inevitably include stuff that was relatively new to the maker when it was made, like "At Your Most Beautiful", a song I fanatically adored (but probably haven't now heard in years). Still, one reason this mix stands out from all the subsequent ones I'd make for this person is that it's much more than a record of what I liked at the time. Of course, '99 was the year I discovered Serge Gainsbourg and Belle and Sebastian, but I still like 'em today. Six years later, my enthusiasm for many other selections here (especially the one-two-three punch of "Everest", "Former Lover", and "Temptation") has not diminished. Maybe that first mix you make for someone is the most pure and inspired--especially when it clicks with whom it's intended for.