No doubt, the question I get asked most frequently when I meet readers of this site is, "Jason, where do you want me to come?" The answer to that one is simple: on the floor, if possible – I just washed my sheets. No doubt, the question I get asked second most frequently when I meet readers of this site is, "Jason, you have incredible taste in music, but how do you organize your music?" That answer is a bit more complicated, but fortunately does not involve any ejaculate errantly landing on my night table.

(Most of the time, at least.)

I’ve recommended hundreds of songs to y’all over the course of the site (just search "Six Songs" in the archive box if you don’t believe me), but I never really got into the best way to store music on your iPod and iTunes. I realized recently that this means that I’ve only been getting you halfway there, because how you arrange your music is just as important as the music itself (this is not true, but bear with me). So for your gratification and to learn you a lil’ bit, here are four of the best ways to organize your personal music collection on your iTunes-based iPod or similar mp3 player.

By Theme
This is the most obvious way to organize music on your iPod, by creating playlists of similarly-themed or similarly-sounding songs. This is a method that I employ with such adroitness that when I think about the perfect playlists I create, I arouse myself. Since the concept is simple enough and doesn’t require additional explanation, below are some examples playlists from my iPod to help further illustrate the idea:

- "Executive Pump Up Mix" — My primary workout mix that ranges from heavy stuff like Black Sabbath’s "Supernaut" to lighter fare like Maroon 5′s "Makes Me Wonder." I know it’s a strange mix, but really, whatever it takes to keep me moving on the treadmill, I’m willing to try.

- "I am a middle-aged black man" — Everything ranging from (more obscure) Otis Redding to Solomon Burke to Curtis Mayfield to Gil Scott-Heron. If you’re black, and in your 50′s, you would like this playlist.

- "Let’s Make Out or Something" — formerly titled "Mood," this is my make-out mix. Yes, laugh if you want, but it’s legit. I recently bedded a ladyfriend who I warned about this playlist before putting it on. She laughed. Her response, a few songs into it: "Ok, this is actually a pretty good playlist." This list contains less-popular (you won’t find U2′s "One" or "In Your Eyes" by Peter Gabriel) mood-enhancing songs like "One By One" (Billy Bragg and Wilco), "You’re Only King Once" (Beulah), "Bubble Gum Years" (Gomez) and "Post-War" (M. Ward), to name a few.

- "New" — Boringly titled and not exactly theme-based, but necessary nonetheless. This is purgatory for any new songs I’ve downloaded, many of them via your recommendation (keep those music recommendations coming, by the way).

- "Sad as Fuck" — If you want to wallow in self-pity, this is your list. The title says it all. Songs like "All My Little Words" (Magnetic Fields), "Valentine’s Day Is Over" by Billy Bragg (the live version with just him and the guitar) and Jeff Buckley’s cover of Dylan’s "Momma, You’ve Been On My Mind." Tread carefully.

- "What? I’m Drinking and Washing My Balls" — The mix I listen to when, well, I’m drinking and washing my balls, getting ready to go out. Similar to "Executive," but without the anger: "Even If You Don’t" by Ween, "Slaveship" by Josh Rouse, and "Time Bomb" by The Format are prime examples.

- "Whiskey, You Son of a Bitch" or "To Hell With You, Woman!" — Pretty much everything ever written by Ryan Adams and George Jones.

Chronologically
This idea is the simplest, but if you’re OCD, it may drive you to murder.

This method was the one I employed on my old PC before I switched all of my music over to my new Mac. I had five basic playlists, representing each of the most recent decades: "60′s", "70′s", "80′s", "90′s" and "00′s" (note that the "60′s" playlist included everything pre-1960 as well). The advantage of this is that you essentially have lil’ radio stations on your iPod. New music in "00′s", oldies in "60′s", high school memories in "90′s", etc.

The disadvantage, which is great, is that this type of organization requires a ton of work. On my old PC, I had roughly 7000 songs – and I organized every last mother fucking one into these categories. This was, as you might imagine, a long and laborious process. Not only that, particular artists gave me fits. For example, I have a Marvin Gaye box set that contains 80 songs from the 60′s to the 80′s. Do you know how stressful it was for me to properly categorize each and every one of these songs? It took me literally weeks to put that bad boy into the proper decades.

(Have I mentioned that I don’t have a girlfriend? Just checking.)

As mentioned, I abandoned this method when I switched computers. Simply, I couldn’t live with the stress of having un-chronologicalized songs on my computer. I was actually losing sleep over whether or not "Can’t You Hear Me Knocking" by the Rolling Stones was 60′s or 70′s (it was released in 1971).

If you have only a small amount of songs that range in eras, this is a good way to go. But if you have over 3000 or so songs, good luck and godspeed.

By Rating
My friend Lauren introduced me to this style of playlist and I think it is highly effective, user-friendly, and most importantly, fluid. iTunes has a built-in feature that allows the user to rank songs on a star system, one star to five stars, both while using iTunes on the computer and when the song comes on the iPod itself. This last part is key. If a song comes on your iPod while you’re walking around Soho, making women uncomfortable by staring at them, breathing heavily, and rubbing pantyhose on your face, and you think, "Damn, this is a great song," with a few clicks you can rank it as a five star song. Then, when you get home and sync your iPod to your iTunes, that ranking is transferred to your iTunes. Fucking sweet.

I use the rating style religiously, mostly because of this fluidity. While it does require ranking each and every song on your iPod, it’s much easier than organizing songs chronologically precisely because you can do it on the fly (whereas you need to be at your computer to move songs into chronological playlists).

I have playlists that are based solely on this star rating system.

- "Fuckin’ A Right" — This list contains only five-star songs, a rating I am very stingy about handing out. I have 8000 songs in my iTunes library and only 75 have five stars. These are songs that I not only find myself listening to every time they randomly come on my iPod, but usually make me weep with delight, rage, or sadness. Fuckin’ A right. Random sampling: "Victoria" by The Kinks, "He’s Gone" by The Grateful Dead, "Ain’t That Enough" by Teenage Fanclub, "Death Letter" by The White Stripes.

- "Seriously Good Shit" — Four and five star songs. There are currently 1417 of these bad boys. To be a four star song, you have to pass one test: If I were driving in my car and this song came on the radio, would I turn it off? If the answer is "no", you get four stars. Random sampling: "A.M. 180" by Grandaddy, "Prison Sex" by Tool, "This Guy’s In Love With You" by Herb Albert, "New Amsterdam" by Elvis Costello.

- "Good Shit" — Three, four and five star songs, totaling 3681. This list is quite a mix because it contains genuinely good songs as well as stupid songs that are worthy of a listen and songs that everyone knows. Examples of these include "Here I Go Again" (Whitesnake), "Pretty Woman" (Roy Orbison), and "All She Wants To Do Is Dance" by Sir Don Henley. Random sampling: "Every Picture Tells A Story" Rod Stewart, "Voodoo Lady" by Ween, "Talk Talk" by Talk Talk, and "Someone Else’s Bell" by Squeeze.

I have no playlists for two and one star songs, because I do not include these on my iPod at all. I don’t like my iPod filled with clutter and shitty songs, so getting that three star rating is really key for a song.

[…]

[I just read this post over and I realize that I sound like a complete, obsessive-compulsive maniac. At least I’m almost done. And if I can help one person – just one person – better organize their music, then it’s worth it.]

[And screw you for judging me.]

By Number of Plays
What better judge of how much you love a song than by how much you’ve played it? This is another organization technique that I employ, breaking songs up into playlists by how many plays they’ve had. It’s all relative depending upon the user, but I have a playlist called the "25+ Gang," which features 56 songs that have been played at least 25 times on my iPod and iTunes. Complementary to this list is the "15+ Gang," which has 156 songs that have been played, um, at least 15 times. This is an easy way to organize music because you only have to periodically sort songs by play count and move them into their respective lists, and as mentioned, there are few better barometers for how much you like a song than how many times you’ve listened to it. There are two problems with this, however.

The first is that songs in certain playlists will be played more often than others, not necessarily because they’re your favorite. For example, I make out a lot. When I do so, I play my "Let’s Make Out or Something" playlist. Therefore, songs on that playlist are played more frequently than other songs, just because I’ll put that playlist on, make out, pass out, and let the list play through and repeat. So the songs in that playlist accumulate play counts more quickly than others based upon their placement in that playlist. Dig? The same goes, to a much lesser extent, to my gym playlist. I wouldn’t consider "Someday" by The Strokes one of my favorite songs, but yet it’s been played 38 times because it’s good a song to run to.

The second caveat is that some songs suffer from what I’ve just right now decided to name the "Sooner Or Later" syndrome. "Sooner Or Later" is a tremendous song by the band Marah that ends with over a minute of an organ outro. Typically, when the song proper ends and the organ outro begins, I’ll skip to the next song, thus robbing "Sooner Or Later" of a play count (off the top of my head, another rocking song with a long outro is Ted Leo’s "Timorous Me," which ends with over forty seconds of screeching feedback). By listening to most of the song but skipping to the next song before the song has played through, I’m hindering these songs inclusion on these play count-based playlists, and thus compromising the integrity of the playlists themselves.

(The most played song on my iTunes? "Echo Park" by Joseph Arthur with 78 plays.)

******

I hope these ideas are helpful to you. If not, at the very least, you have learned something new today: I am borderline obsessive compulsive. And I have learned something new today: Perhaps my borderline obsessive compulsive is related to my functional impotence, specifically how I can only get erections at funeral. I’m gonna think about this one for a bit.