1.) First Generation iPod

Although the iPod is still as popular today as it’s ever been, the specifics of the product have changed greatly since the first iPod came out in October 2001. Originally containing a mechanical scroll wheel, the device could hold up to 5GB of music. The wheeled iPod is currently branded as the “iPod Classic”

2.) Sony Walkman

The first ever portable music player changed the way people consumed music. Using tape cassettes, the on the go music player became instantly popular.

3.) Sony Minidisc

Sony launched the Mini-Disc in 1992 where it only sold 50,000 devices within the first year.

4.) Sony Discman

Released in 1984, the portable music player was brought to the public two years after CD’s had started to become mass produced. The initial device, the D-50 retailed for $350.

5.) Laser Disc

The first optical disc to be used for home media. First available on the market in 1978, the discs are roughly 5 times larger than a standard DVD disc. The technology behind the Laser Disc laid the foundation for future media resources such as the CD, DVD, and Blu-Ray DVD.

6.) Audio Technica Sound Burger

Ever wanted a convenient way to show off your record collection and have that true vinyl sound on the go? Say hello to the Sound Burger by Audio Technica. Unfortunately you couldn’t strap it on to you and go, the device only worked while on a solid surface.

7.) AMFM Headphones

Made popular by Steve Bartman, these devices used to be seen all over sports stadiums to allow fans to listen to play by play broadcasts of their hometown announcers while watching the game live. Also a great way to get your XRT fix on the go.

8.) Apple Power CD

One of Apple’s first attempts to integrate their products. The CD player could be purchased as an add on to Apple speakers and was able to read audio, photo, and data CD’s.

9.) MPMan F10 MP3 Player

The first mass produced MP3 player made its debut in 1998 from the South Korean company SaeHan Information Systems. The players came in either 32MB or 64MB models with the 32MB device selling for $200-$250.

10.) Rampage Portable VCR Player

Imagine if everyone on the L that was streaming Netflix, Hulu, or YouTube on their phone carried one of these around to watch video.

11.) VideoNow

This portable video device only played custom four inch discs. Holding up to a maximum of 30 minutes of content, each video plays in black and white.

12.) HitClips

Made out of similar technology of a memory card of a digital camera, HitClips played one minute of a song. Helping to make pop sensations like ‘N Sync and Britney Spears the pop culture icons they were. The device grossed over $80 million.

13.) Boombox

Nothing defines old school cool more than this. Unfortunately boomboxes are becoming harder to find and there is a disappointing lack of people walking down the street rocking a boombox on their shoulder.

14.) Nintendo Gameboy

One of the first portable video game systems, the Game Boy has become a cult classic. Selling over 118 million devices in its history, the Game Boy has been enshrined as one of the best gaming systems of all time.

15.) Tiger Handheld LCD Games

When discussing 90’s culture, it would be hard not to mention these games as staples. Each game came as a separate device and with over 100 games to choose from, it was easy to stockpile a drawer’s worth of games.

16.) Portable DVD Player

First released in 1998, the very first portable DVD players would retail for around $1000. With instant streaming services like Netflix and Hulu now available, these devices are not nearly as practical as they once were.

17.) Seiko TV Watch

Such a cool concept but the device did not carry much commercial success. Released in 1982, the watch had a 1.1 inch screen that required the user to be connected to a portable receiver at the time.

18.) Sega Game Gear

Released as the main competitor to Nintendo’s Game Boy, Sega’s Game Gear featured a larger screen along with colored game play. Oddly enough, Nintendo announced in 2011 that their 3DS virtual console will feature old Game Gear games.

19.) Apple Newton PDA

Apple’s version of the PDA has widely been labeled as one of the biggest failures in Apple’s history. With over $100 million spent on developing the product, Apple could never decide whether to use the PDA as a standalone product or as a component to existing device.

20.) 8 Track Player

What used to be the standard broadcast cart format at radio stations was found in most cars throughout the 60’s and 70’s. In some cases, 8 track tapes were set up to be played straight through like some albums were arranged.