It’s Weird ’90s Week on Stereogum. All week long we’re looking at the strangest musical moments and trends of the decade. Check out more here.

The ’90s were the last gasp of a music industry coasting on hubris. Its longstanding structures were famously shook down — if not straight-up taken down — in the decade’s last few months by the introduction and widespread adoption of Napster and its normalization of music as a zero-cost listener investment. And in the nine-year run-up to that foundation-rattling moment, music fans also had to reckon with the irritating wastefulness of the longbox (which wasn’t discontinued until 1993), the lossless Digital Audio Tape being commercially smothered in the United States by the RIAA over copyright-violation panic, the phasing out of the wide-release single in favor of the more lucrative single-and-filler full-length, Garth Brooks’s (unsuccessful) push against used CD sales, repeated yielding to Wal-Mart-enforced censorship, and a set-in-stone pushing-$20 price point for CDs that bordered on the usurious. All this while the industry was making the kind of profits that it had only dreamed about during the market-glutting ’70s or the tentpole-album ’80s.

That’s probably why there’s so much ridiculousness in the era’s tinkering countless new formats, all but one of which turned out to be less popular than the CD/cassette/vinyl triumvirate that traditionally drove sales in the previous decade. The ’90s music industry was nothing if not a masterclass in consumer-gouging, and considering how many efforts by labels and electronics manufacturers alike absolutely turfed out, it seems lucky in retrospect that things didn’t get worse. After all, the same RIAA push that killed the DAT as a possible successor to the cassette tape uncharacteristically yielded to computer manufacturers’ demands to be exempt from 1992’s Audio Home Recording Act — which proved to be a problem for the record business when CD burners started coming standard with new desktops. So let’s salute some of the industry’s attempts to find new ways to sell us music in the ’90s — as well as a few more successful ways people found out how to get it for free.

Waveform Audio File Format (.WAV) (1991)

One of the most enduring digital audio formats available since its early ’90s introduction, the .WAV isn’t exactly a Sam Goody stock item. But it’s long been the standard for lossless digital audio — whether for professional sound editors, sample-based producers, or home-mix-CD burners. A proprietary format co-developed by IBM and Microsoft for Windows 3.1, there’s not a lot of exciting backstory to the .WAV, but considering how integral it’s been to operating systems it’s easily one of the most-heard, most-used audio formats in existence. (This could technically make Brian Eno’s Windows 95 startup “Microsoft Sound” the format’s answer to Thriller.)

Digital Compact Cassette (1992)

MiniDisc (1992)

Philips and Sony had collaborated on the creation of the modern Compact Disc starting in 1979, developing the Red Book standard in 1980 and collaborating to ensure that CDs and CD drives would have widespread, universal hardware compatibility. But as competitors, they’d wind up launching their own separate new format concepts in the same year — neither of which entirely caught on, especially at a point when the market for records was already split between cassettes and CDs. Philips’ Digital Compact Cassette was an attempt to create a more advanced audiotape variant, simultaneously marketed as a cheaper alternative to DAT while still being more state-of-the-art than the decades-old standard cassette. It had a sliding data-protection door like a 3.5″ floppy disk, loaded into the DCC player tray like a VCR, and featured encoded data that would allow the player to jump to the beginning of any track on the tape without making the user fast-forward and hope for the best. But even the DCC player’s promise of backwards compatibility with standard cassettes couldn’t move units, and the format was discontinued in 1996 with less than 250 titles seeing release in the format. Sony’s own offering, the MiniDisc, could be said to have won just off longevity alone — though what advantages there might have been to having a slightly more portable format was severely mitigated by the inferior audio compression of the ATRAC codec and the dearth of early adopters in the record industry. The discs were recordable, but blanks were expensive, as were the players, and the emergence of CD-Rs by the middle of the decade eroded what little market share the MiniDisc had outside Japan. Some DIY musicians still record onto them for demos and limited-edition releases, but otherwise it’s a forgotten format, scarce consolation for Sony losing the VHS-Betamax wars.

DVD-Audio (1999)

Super Audio CD (1999)

If the format war between the Digital Compact Cassette and the MiniDisc was a battle of attrition based around total impracticality, the one between DVD-Audio and Super Audio CD was a tired shrug of a feud that flailed through redundant irrelevance. The question wasn’t whether one sounded better than the other — with a comparable capability to store more data than standard CDs, and multiple options for multichannel playback, blind listening tests revealed little discernible difference between the two. The issue was whether they even sounded better than standard discs in the first place. And after a September 2007 study, a damn-near-definitive conclusion arose: oh heck no way they were not. Some audiophiles complained at the study’s results, their rage possibly correlating to how much time they spent trying to bypass DVD-Audio’s convoluted, preamp-nerfing copy-protection measures or how quick they were to buy Sony’s $5,000 (!) SCD-1 SACD player. When you’ve lost the gearheads, there’s nobody left to pick up the slack when ordinary consumers blanch at the investment; naturally, both formats were irrelevant by the end of the ’00s. Then again, when the entire record industry spent the mid-late ’90s ramping up the nuance-destroying brickwall levels thanks to the loudness war, audiophilia itself could’ve been the real casualty of all this.

RealAudio (1995)

Streaming audio… on the internet? RealAudio made that possible, or at least that’s the format that gets the credit; Progessive Networks launched the first version of the audio-streaming technology in April ’95 after the multicast backbone known as the M-bone proved the viability of live internet broadcasting. Less than a year and a half later, RealAudio 3.0 debuted with an audio quality comparable to Stereo FM over 28.8 kbps modems — and if having that touted as a spectacular breakthrough didn’t sound 1996 enough to you, keep in mind that A&M Records marked the occasion by using the service to broadcast the debut of Sheryl Crow’s single “Hard To Make A Stand”. (Crow’s official statement on the event: “RealAudio 3.0 rocks!“) For the next several years, RealAudio held a presence as a sort of by-default format for the next few years, but media-streaming inroads by a competitor in Microsoft’s NetShow — later Windows Media — took a decent-sized chunk out of their dominance, and the bursting of the dot-com bubble finished what a receding demand for ephemeral livestreaming audio started. RealNetworks made a point of suing Microsoft with an antitrust lawsuit based around Windows bundling Windows Media Player with the OS. But even after receiving a nearly half-billion-dollar settlement in the case, RealNetworks never quite regained that same level of prominence in a media landscape now dominated by Spotify, Pandora, and Apple. And within 10 years of Sheryl Crow’s endorsement, RealPlayer had earned a rep as a complete privacy-violating nuisance of a software package, to the point that PCWorld ranked it second only to America Online as one of the worst tech products of all time.

MP3 (1993)

And so we come to the one real lasting legacy of the ’90s format frenzy — a digital standard that wasn’t super-high-fidelity or readily monetized by the record industry or packed into a tech advancement any fancier than a new codec and a freeware copy of Winamp (“it really whips the llama’s ass”). But dang, MP3s were pretty damned portable — easy to share, easy to burn, easy to make into customized playlists, and real easy to download en masse. Karlheinz Brandenburg’s 1989 Ph.D dissertation on digital audio compression was the end result of intense research that dated back to the early ’80s. And Brandenburg’s team of German electrical engineers — using the original a cappella version of Suzanne Vega’s “Tom’s Diner” as a test bed — eventually nailed down the MP3 as we know it by 1991. They submitted their proposal to the International Organization For Standardization’s subgroup known as the Moving Picture Experts Group — their abbreviation, MPEG, should ring a few bells — and after consolidating a handful of similar proposals, the standard of ISO-MPEG-1 Audio Layer 3 was established, with its first public release in 1993.

The following year, Fraunhofer l3enc became the first software that could convert .WAV files to the MP3 format. The following year, the official .mp3 filename extension was established, and WinPlay3, the first real-time MP3 software player, was made available. The year after that, a warez organization called Rabid Neurosis formed, and eventually became one of the first and most notorious groups dedicated to leaking albums in MP3 form. And the year after that, the launch of both Winamp and the independent artist-bolstered site mp3.com gave the fledgling format the legitimacy that would eventually make it the definitive audio format of the ’00s. By the end of the ’90s, Shawn Fanning — who was roughly the same age as the file format he’d wind up spreading to millions of hard drives — had a long-building base of interest to help make Napster the phenomenon it was. That the most successful new format of the ’90s was the most damaging one to the record industry … that pretty much says everything, doesn’t it?