I think about this album all the time. There are just times throughout my week that a tune from Of Montreal’s best album, The Gay Parade float into my head, and I end up whistling the melodies to “Old Familiar Way” or “Neat Little Domestic Life.” This is an album from a very specific moment in the indie music landscape, and Of Montreal’s reign as the height of whimsical indie pop was firmly established on this album. It’s not their only great album in this specific style, with Coquelicot Asleep in the Poppies and (to a certain extent) Aldhils Arboretum both continuing the style.

After that? It’s a totally different band, and yeah, obviously Kevin Barnes is the through-line, I find it difficult to match, say, The Sunlandic Twins with The Gay Parade. Good for the band, good for Kevin Barnes, all that — I’m not feeling resentful about it, and I can find room in my heart for both iterations of the band’s style. But it’s sure different, isn’t it? It’s all playful, but in decidedly different ways. And maybe that’s the through-line — that playfulness.

This album has so many amazing songs contained within. “Old Familiar Way” is a perfect opener; “Fun Loving Nun” with its incredible use of an organ, both for musical and lyrical reasons; “Jacques Lemure,” which might be the best song ever written about a volunteer fireman; “Neat Little Domestic Life,” which is as lovely a pop song as anything that came out in 1999; and, of course, “My Favorite Boxer,” about the fictional Hector Ormano.

I listened to this album so much in high school. Of any album on this list so far, it’s absolutely the one that I listened to the most within five years of its release. And you know what? I still go back to The Gay Parade sometimes, and I’m always happy I did. There are some songs I’m happy to skip these days, but that’s why this album is at #27 and not, say, #7.

A few things I learned while writing about this album:

• Kevin Barnes played keyboard on the Bright Eyes album Letting off the Happiness, which came just a year before this album. Isn’t that something!
• I guess I only needed one bullet point here. I did learn a bunch, but did I learn anything I can put a finger on? Not really. Hmm. Sorry?
• Anyway, this album reminds me that I really should listen to more psychedelic pop. You know, the stuff that’s all shockingly just about to turn 60 years old.