I kicked off 1999 not with that Prince song (the Chicago bar I attended that New Year’s Eve played the intro before its patrons verbally demanded a cease-and-desist) but by falling deep into 1996’s If You’re Feeling Sinister, a premonition. This was one of the more disjointed and new music-deficient years of my life. Between stumbling across the finish line of grad school and desperately seeking steady employment, I took a four month long mental health break from doing much of anything (“A Summer Wasting”, if you will), leaving me with no money to spend on music. I adapted accordingly, raiding a plethora of suburban libraries to acquire previously unheard (i.e.—old) stuff ripe for discovery (Nina Simone, Serge Gainsbourg, Os Mutantes, etc.) Still, even if I had had the cash, it’s not like I’d have been rushing out to buy any of the year’s best-sellers.

What endures from this transitional period is something of a grab bag. We have tracks from both long-beloved artists—a sweet sigh from Everything But The Girl’s last album (until 2023!), Aimee Mann’s Magnolia soundtrack triumph, another indelibly-titled Pet Shop Boys single—and good stuff I didn’t hear until much later: Le Tigre’s unstoppable party anthem (not fully appreciated by me until its inclusion in the 2006 film Reprise), Super Furry Animals’ Tropicalia-by-way-of-Wales, The Negro Problem essaying a heavenly ballad leader Stew would include in his Tony-winning musical nearly a decade later. And yet, I recognize selections I knew and loved at the time, like the lead-off track to Beth Orton’s mostly forgotten second album, Ben Folds Five’s flop follow-up to “Brick” (how did their label think that could be a hit in the mook-rock era?!), Blondie’s underrated (in the US, anyway) reunion single and an Indigo Girls tune that didn’t trouble the pop charts but received heavy rotation on Boston’s WBOS (then a decent Triple-A station).

Of course, I was never going to hear The Magnetic Fields or Sleater-Kinney without actively seeking them out. Same goes for Jason Falkner, whose second LP Can You Still Feel was a lucky library find not long after its release. As for Fiona Apple’s impossibly-titled second album (which I picked up in early 2000), today it less resembles 1999 than an ongoing future/past/present, even on such heavily indebted-to-the-past (in this case, the Beatles and the Great American Songbook) three-minute masterworks like “Paper Bag”.

1999: When It Costs Too Much To Love

1. Le Tigre, “Deceptacon”
2. Beth Orton, “Stolen Car”
3. Jason Falkner, “The Plan”
4. Everything But The Girl, “No Difference”
5. Supergrass, “Moving”
6. Fiona Apple, “Paper Bag”
7. Pet Shop Boys, “You Only Tell Me You Love Me When You’re Drunk”
8. Tom Waits, “Hold On”
9. Tori Amos, “Bliss”
10. Aimee Mann, “Save Me”
11. Steve Wynn, “Cats and Dogs”
12. Ben Folds Five, “Army”
13. The Magnetic Fields, “All My Little Words”
14. Hedwig and the Angry Inch, “Wicked Little Town”
15. Blur, “Coffee and TV”
16. Indigo Girls, “Peace Tonight”
17. Fountains of Wayne, “Red Dragon Tattoo”
18. Meshell Ndegeocello, “Bitter”
19. Moby, “Why Does My Heart Feel So Bad?”
20. Sleater-Kinney, “Don’t Talk Like”
21. Blondie, “Maria”
22. Super Furry Animals, “Northern Lites”
23. Guster, “Fa Fa”
24. Ani DiFranco, “Everest”
25. Roxette, “Wish I Could Fly”
26. Delirium feat. Sarah McLachlan, “Silence”
27. Cibo Matto, “Spoon”
28. Emm Gryner, “Disco Lights”
29. Dido, “Here With Me”
30. The Negro Problem, “Come Down Now”
31. Madonna, “Beautiful Stranger”
32. The Chemical Brothers, “Let Forever Be”
33. R.E.M., “The Great Beyond”