I remember walking into my friend’s dorm room one day back in the late 90’s. He wasn’t there, but all the lights were on and Phil Collins’ In The Air Tonight was playing on his computer. Back in those archaic times, using your computer as a stereo system was still something of a novelty. Only recently had I acquired a computer that had a color monitor AND could connect to the internet. I could log on to wellsfargo.com and check my account balance any time I wanted! From my computer! The future had arrived! Well, sorta. It took a little while longer before the “dot com” boom actually boomed. In the meantime I was sated by checking my meager bank funds eight times a day, much to the annoyance of my roommates who wanted to use the phone line for things like, you know, making phone calls. Ahhh, I almost miss the ol’ bang-and-shudder of that dial-up modem. But that computer was no jukebox. Before “mp3” had even entered my vocabulary, I had close to 500 CDs to suit my every musical whimsy, carefully alphabetized on a nifty spinning carousel rack, plus maybe fifty tapes. (Yeah, CASSETTES! Remember those?) The jukebox in my life was a mini shelf system my parents bought me for Christmas back when I still thought Vanilla Ice was cool. 
It had a three disk carousel changer, two tape players, and a clear top so I could watch the disks twirl around, which was very exciting. (I’m nothing if not easily amused.) With this technological marvel I could keep up to around 40 CD-bound songs continuously on tap and could dub to tape, an important feature before the arrival cheap CD burners and recordable disks. (The exchange of mixtapes as a cultural expression of friendship and goodwill put the phrase “I’ll make ya a tape” right up there with “There’s an app for that.”) Never mind that once a year the CD player would start skipping and stuttering worse than that Max Headroom guy until I took it in for a professional cleaning. I grew up on tapes, so just the fact that you could skip directly to the good tracks made CDs totally worth it. (Anyone else remember the days of FF, Play, FF, Play, FF, Play—Crap I went too far—Rewind, Play, Rewind, Play…?) Sure, they sound better too. Whatever. Gimmie the good song! Now! But you know what would be even better? The artist and song name displayed on the player. And now, finally, I could see on my friend’s computer monitor, indeed, the future had arrived. Displayed in Winamp 1’s original green-on-black font, scrolling back and forth, was “Phil Collins – In The Air tonight”. Never mind that it only scrolled one character width at a time like cheap Christmas lights, that was still cool shit!
It remains a mystery why I remember the exact song that was playing when I first gazed upon Winamp’s countenance. Could be just that I really like that song, however unfashionable Phil Collins may be at the moment. It’s amusing how we, as a culture, jump on these totally unjustified bandwagons either dethroning or glorifying our icons. I mean, seriously, despite the recent spate of Chuck-Norris-is-so-cool one liners, truthfully he’s kind of a geek. Not that that’s a bad thing, but how is it that a conservative, uber-religious, mild mannered, B-rated actor well past middle age rather suddenly became “cool”? Meanwhile, Phil Collins gets the opposite treatment to such an extent that he felt compelled to publically assuage fears that this treatment had precipitated his retirement. Few people actually think much one way or another about either man, though nearly everyone likes to feel ‘part of the group’. We’re such lemmings. But I digress…
So there I was, 14-ish years ago, ogling Winamp on my friends’ computer, barely understanding that CDs come encoded with “data” which can be extracted to audio files and played on a computer. Interesting, but not very practical. With a 5 GB hard drive on my laptop, I simply didn’t have room for very much music. Besides, I certainly wasn’t going to bust out my laptop every time I wanted to listen to some tunes. (Connect my laptop to external speakers? You can do that?) But a couple years later, it was a whole new world: Napster suddenly went mainstream, I got a new computer with waaaaay more storage space, and mp3 players (as they were called before iPods monopolized the market) were EV-REE-WHERE. Just like everyone else in the herd, I steadily gravitated away from CDs and toward mp3s. Eventually I ripped my entire collection and sold the all disks off in one shebang on eBay. (Weird. I haven’t thought about eBay in a loooong time. Looks like they’re still doing well. I’m kinda surprised.) Soon the only CDs I still used were filled to the brim with mp3 files. Gone forever were the days of only 12 measly songs per disk. Gone, too, was my mini shelf system with the 3 disk carousel. And throughout it all, Winamp was my media player of choice.
For the longest time, Winamp seemed vastly superior to other media players, all of which struck me as clunky or bloated or both. Even though I had a brief love affair with iTunes after I got my first iPod, it didn’t last long. Whereas Winamp lets you tweek just everything about it, iTunes is generally resistant to change. Going from one to the other feels a bit like prancing around naked just prior to donning a straitjacket. So back to Winamp I went. Oh, maybe I was just used to Winamp, I don’t know. Maybe it was some misplaced loyalty. But somehow something always seemed to be missing from other players. Like global hotkeys or desktop popup notifications or the ability to write a quick query right there in the UI to return a very specific list of songs. Plus, and this was a biggie, ShoutCast radio isn’t supported everywhere and that was an absolute must-have.
The problem was that Winamp increasingly felt outdated. When I think back to when I first discovered it in my friend’s dorm room, I’m reminded that its interface hasn’t changed much since 1997. Sure, the text scrolling is much smoother now, but that sort of thing just isn’t impressive anymore. I could skin the UI if I wanted—there’s roughly 1 trillion skins available on winamp.com—but they all seem too cheap or too flashy or as outdated as the native UI itself. As time went on and Winamp seemed permanently stuck in the purgatory of version 5.0, I found myself looking for a newer, fresher alternative.
Unfortunately, googling “media players” just yielded the same old hits. Winamp. Windows Media Player. VideoLAN. I found some “best of” lists which led me to the likes of MediaMonkey and Songbird. All of them had serious flaws that I can’t even recall at the moment, even though some—Songbird in particular—had pretty nice UIs. This was depressing. Winamp, anachronistically, still reigned supreme.
When I finally found a media player good enough to unseat Winamp, it wasn’t in the form a desktop app. Since I’ve historically been completely disinterested in subscription-based streaming services, it was quite a surprise when I found—and loved—Rdio.com. I liked it so much that I was willing to let go of some features I thought I couldn’t sacrifice. It includes no global hotkeys and no desktop notification when the song changes. Hell, it doesn’t even display the name of the song in the browser tab title. All major irritants, but among other winning features, the UI is elegantly simplistic and 95% of the music I want to hear is available. Pandora-style “radio stations” are nice sometimes—and Rdio has those too—but most of the time I want to hear the full album from a particular artist. I went crazy the first few months on Rdio, listening to albums I was scared to pay $9.99 for because there was a strong chance the one song I had already heard would be the only good one. Also, Rdio has most of the music I already own, nicely organized. My mp3 collection is a 106GB disaster zone, replete with duplicates and triplicates, mangled ID3 tag information, and sub-128/kbps files. Remnants of those wild Napster days and exchanges among friends of large mp3 filled hard drives. Now when I click on The Joshua Tree, I only get one of each track in my playlist. Ahhhh!
The final nail in Winamp’s coffin came when I built a new computer in November and was reinstalling all my software. When Winamp’s number came up, I hesitated. Instead, I gave Windows Media Player 12 a whirl. Since I now did most of my music listening online, away from my local mp3 collection, I deemed WMP “good enough” and forewent the Winamp install. For the first time in almost 15 years, I have a computer that is sans-Winamp. Between Rdio.com, ShoutCast.com, and RadioParadise.com, I’m pretty satisfied. Excluding my car, where I permanently keep an old 30GB iPod, there’s only been a handful of times I had to dig back into my local collection to hear what I wanted.
I’d like to think NullSoft/AOL will eventually spawn Winamp 6.0 and give it’s awesome feature set a fresh look, but given that there hasn’t been a major release since version 5.0 in 2003, I’m not holding my breath.