I don’t know what you did during Thanksgiving break, but I wasted most of mine trying to order an impossible list. 

I also ate pie. (Though not nearly as much as I wanted).

Ok, first things first, I went into Thanksgiving vacation with plans to do jack shit. There would be intentionally bad Netflix choices and lots of sitting around in my PJs, of course, but not much else.  After the a few traumatic years— three with a cancer-stricken mom worrying/enjoying through what would potentially be the “last one” and then last year trying to rally through the traditions as an orphan who never even liked “The Holidays” in the first place —this was the year of togetherness with my emotionally exhausted nuclear family expending as little effort as possible.

The thing about having no schedule and no place to report to is that it frees up a lot of time and headspace. And I’m sure if you’ve been reading my column, I’ve told you already that being alone with thoughts is not my favorite.

So there had to be some kind of task to occupy my mind while remaining as physically idle as possible.

Somehow I decided refining one of my playlists in iTunes would be an amusing time suck. Jen’s Top 500 seemed the obvious choice.

I know, just the title sounds daunting, but honestly when I threw 500 songs into a playlist over the summer I didn’t think much about it. I captioned it, “The playlist to be played at my funeral or really any event where you are celebrating me.”  But it wasn’t really in any order.

Because who would be daft enough to rank 500 of their favorite songs?

Well, me, last weekend. And when I say last weekend, it took all four days and then I spent a more than a couple hours messing with it this week too.

The list is public on Apple Music and you are free to giggle and gawk at it. I’m not claiming its the 500 best songs, but they are my ordered favorites. Though crafting this list gave me very little pleasure.  It was hella stressful. (And I remind you that pot is legal in California). 

But it’s something I challenge you all to do. Maybe not 500 songs because that’s just ridiculous, but when you start listing you’ll find 100 is too little and any other number just sounds random and weird.

Also with 500 songs you are allowed to not take yourself so seriously. It gives you the freedom to add the guilty pleasures. But you have to compare and contrast songs of many genres and that is a challenge.

Does a perfectly crafted song trump sentimentality? What does it say if your wedding song can’t make it into the Top 50? Is it fair to put a ballad that makes you fall into a soggy pile of tears every single time to your personal dance anthem?

Every song deserves a “why” as it moves up and down the list to its eventual home and that leads to some serious self-reflection and disgust. Or maybe that’s just me.

It also becomes quite a mess toward the middle. When you can’t just see/hear all the songs at once it’s difficult to know if you treating the ones at the end fairly. I mean, yes #283 – “It Won’t Be Long” by The Beatles is better than “A Little Fall of Rain” from Les Mis, but there are some really great songs in the low 400’s like Lou Reed’s “Satellite of Love” that might have stood a better chance in comparison had it not been added originally with songs like “As Tears Go By” by The Rolling Stones or “Because I Do” by X standing between them the mid-300’s. Like life, ranking isn’t fair. It’s about what got added first and the competitors in their immediate neighborhood.

At the end of this I didn’t learn much that I didn’t already know, but I was reminded of some things I’d forgotten. Like, for one, how much I’ve changed. I say “changed” very specifically because, as I was reminded, we don’t really always grow, sometimes we regress, sometimes we veer into really freaky tangents, and then sometimes we bullshit ourselves into pretending we’re better than we are and that turns out to be some excellent fertilizer.

Music is an excellent way to drive through your psyche. Try it.

It’s also a pretty good way to get some stats on what a total nerd you are. Though that I would immediately start collecting stats kind of already tells you what kind of a nerd I am.

In any case, behold these, perhaps slightly embarrassing, facts about me:

The band with the most songs is 10,000 Maniacs (19 – not counting another two from Natalie Merchant solo) with Liz Phair (15), X (14), and U2 (11) trailing behind. I would have told you last week that I don’t really like U2 that much and I wouldn’t have known I was a liar.

There are multiple songs I hijacked from my kids’ music. Hey Taylor Swift! Hey Miley Cyrus! (But spending time with my daughters tells my story too, so duh!)

“Wicked Little Town” from Hedwig and the Angry Inch shows up in 4 different versions on the list, yet the first appearance of it isn’t until Lena Hall’s at 211.  And arguably it isn’t even my favorite song from Hedwig. “The Origin of Love” is at #36

Among the genres there is everything from musicals to punk to sugary pop to singer-songwriters, but it’s very mid-1990’s heavy which would indicate that I was probably happiest in my mid-twenties. This would have been news to me in my actual twenties.

If you take me up on the challenge, please make sure to leave a comment on where I can listen!