Version 1.1

Classic version of iTunes. It improved visual effects and it bundled with Mac OSX v10.0. The bundling was what made this version a standout. Don’t get me wrong, I was pleased with the improved visual effects, but that’s just an aesthetic upgrade, or what I like to call the shallow part of the version. The bundling, though, the bundling was the core. The first version of iTunes didn’t bundle with Mac OSX v10.0 at all, and to be honest—and please excuse my language here—that really fucking pissed me the fuck off. My thinking at the time was, if you’re going to do iTunes, and put in all that effort into doing iTunes, you might as well do it right. Right? You have to bundle it. Heck, you bundle until you’re blue in the goddamn face as far as I’m concerned. You can’t bundle enough, is what I’m trying to say. Understand? It just makes sense. So after this update, I knew the people at iTunes knew that bundling was important, which gave me confidence in the product going forward. Confidence in things is good. That’s why this version—and I’m speaking specifically about the bundling—is one of my favorites.

Version 2.0

Many of you know I am a huge sound guy. I am very big into sound enhancers, cross fading, and equalizing. So, I was pretty thrilled when this version of iTunes added sound enhancers, cross fading, and equalizing. When it came out, I must have spent four months straight just sitting in my apartment enhancing the sound of my music, cross fading it, and then equalizing it. I became a legend in my neighborhood for doing that.

Version 4.9

Seven words: Motorola ROKR E1 mobile phone support added.

iTunes version 7.0.2

In order to talk properly about 7.0.2, I think we need to take a step back and look at the embarrassment that was 7.0.1. It was an embarrassment to me, my family, and to God. On paper, it sounded good: Video playback/purchasing improvements, iPod games, major GUI changes, gapless playback, sync purchase content from iPod to computer, and cover flow added. Yes, I like cover flow a lot. However, let’s be honest here, were the GUI changes really that major? I would say no. I would say they seemed like pretty minor GUI changes. Pardon me, but when I hear the word “major,” I’m expecting something revolutionary, a bold leap forward, a brand new way of approaching the GUI. If you asked someone what he remembered about iTunes version 7.0.1, they wouldn’t say the brilliant GUI. They would say that this was when iTunes lied directly to our faces and made us feel like fools. This was the version of iTunes that spit on our grandparents’ graves, took a plastic bag, and put it over our heads until we suffocated and begged for mercy. This was the version of iTunes that showed us Hell and made us wonder, “If the world can be this dishonest and horrific, do we even want to live in it?”

Version 7.0.2 fixed all that stuff I just talked about.

Version 10.2.3

This was a good one!!!!!!!!!!! A really good one!!!!!!!!!!!!!!!!!

Version 10.7

This is sort of one for the niches. But if you were the type of person (and I totally was) who kept on asking yourself, “When is iTunes going to drop its support for PowerPC-based Macintosh processors,” then this update was for you. If you weren’t that type of person, this pick probably doesn’t resonate with you as much, so let the hate mail roll in, I guess.

Version 11.0.3

This is a sentimental pick with a story behind it. I was 10 years old, and my dad came home from work after a long day at the shop. I always got excited when the old man came home because it excited me. So I ran down to hug my father, and he said, “Seth, I have a present for you.” The second he said that, I knew it was version 11.0.3 of iTunes. I had been talking about it forever. How he afforded it I’ll never know because my dad was $350,000 in debt and only made $4,000 dollars per year. Anyway, he opened up his briefcase and gave me the new version, and I asked him, “Does this have a new feature that allows the MiniPlayer to be tweaked so that it can show album art, while at the same time keeping the player controls hidden? Also, does it reinstate the MiniPlayer progress bar?”

He just started crying.

You see, mom passed away 40 years ago and it was just us. Also, we weren’t exactly living in a house at the time. It’s hard to describe but it was more like a small, enclosed space with no rooms whatsoever. It wasn’t a studio so don’t think that. There was garbage everywhere—just mounds and mounds of trash. And I think that any time we were able to have these father-son moments where all the pain went away, dad would become very emotional. So this one holds a very special place in my heart.