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Regency TR-1
This is where carrying music around begins. The TR-1 reached U.S. stores in October 1954 at $49.95, built around four germanium transistors from Texas Instruments, and it was the first transistor radio American shoppers could buy.
You could not choose the songs, only the station, but you could take the station anywhere in a coat pocket. More than 100,000 were sold, enough to put the word "transistor" into everyday speech. Every pocket player after it, from cassette to hard drive, owes something to the idea that music no longer needed a living room.
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Walkman
Sony Walkman TPS-L2, 1979
The player that made private listening in public normal. It went on sale in Japan on July 1, 1979, for ¥33,000, and cost $200 when it reached the U.S., where buyers in 1980 faced a month-long wait for stock.
What makes the first model worth knowing is how sociable Sony assumed it would be. It had two headphone sockets, and an orange "hotline" button faded the tape down so you could talk to the person beside you without taking your headphones off. Its successor, the WM-2, dropped the hotline for a simple mute button on the headphone cord, an early sign of how quickly people embraced listening alone.
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Discman
Sony D-50 Discman, 1984
The D-50 put the compact disc in a bag barely two years after the format arrived. It appeared in Japan in 1984 and was the first of Sony's Discman family, measuring roughly 126 by 130 mm and only 39 mm thick. The story that it was designed to be no deeper than four stacked CD cases is often told, though it may be more legend than brief.
It was not cheap: the first British buyers paid £279.99. It still mattered, because it turned digital sound from something that lived on the hi-fi into something you could carry to a friend's house, and it gave the Discman name to a whole generation of portable CD players.
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Walkman
Sony Sports Walkman WM-F5, early 1980s
The first Sports Walkman took the cassette player outdoors, into the kind of weather and activity that would have ruined an ordinary one. Sony fitted soft rubber seals around every opening to make it splash proof, and it added a built-in FM radio.
Its loud yellow case became the standard livery for the Sports models that followed, which is why a yellow Walkman still reads as the 1980s at a glance. For anyone who ran or cycled with music, this is the model that showed a player could be rugged as well as small. Sources date its debut to 1983 or 1984, so expect both years in listings.
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MiniDisc
Sony MZ-1 MiniDisc Walkman, 1992
The MZ-1 introduced MiniDisc, and with it the idea that you could record your own digital mixes onto a disc small enough for a shirt pocket. It used the first version of Sony's ATRAC compression and recorded up to 74 minutes, from a microphone, a line input or an optical digital feed.
As a first model it was too big, too expensive and short on battery next to cassette Walkmans, and collectors should know that. The format it launched went on to win a devoted following as the mixtape medium of the 1990s, with tracks you could erase or combine in seconds while the rest renumbered themselves, which made it the closest thing to a playlist before MP3.
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MPMan
Saehan MPMan F10, 1998
Before the Rio got the headlines, a South Korean company got there first. Saehan launched the F10 in March 1998, and it is widely credited as the first commercially released portable player that could handle MP3 files. It held 32MB of flash memory, enough for only a handful of songs at 128Kb/s, and loaded them over a PC's parallel port.
In the U.S. it sold for $250, later $200. Nothing moved, so nothing skipped, and that is the real breakthrough here: music as a file rather than a physical thing you had to carry.
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Rio PMP300
Diamond Rio PMP300, 1998
The Rio matters as much for the courtroom as for the hardware. Released in September 1998 at $200 with 32MB of memory and a SmartMedia slot for more, it was sued by the Recording Industry Association of America within weeks.
The RIAA lost. A judge refused to block sales, the appeals court held that the Rio fell outside the Audio Home Recording Act because it could not copy from CDs, tapes or broadcasts, and the two sides later dropped their litigation. That outcome helped clear the way for the MP3 players that followed, the iPod included, which is reason enough to know this modest-looking player.
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Creative Nomad
Creative Nomad Jukebox, 2000
This is the answer to anyone who thinks the iPod invented the pocket music library. Creative began shipping the Nomad Jukebox in the U.S. on September 18, 2000, with a 6GB hard drive holding over 100 hours of music, roughly 150 CDs' worth, more than a year before Apple's player.
The catch was size and price: it was about as big as a portable CD player and cost $499.99. That bulk is exactly why it belongs here. It proved people wanted their whole collection with them, and it set the target the iPod would hit in a far smaller case.
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IPod Classic
Apple iPod, first generation, 2001
Apple did not invent the hard-drive player, but it made one people actually wanted to carry. The original iPod put 1,000 songs on a 5GB drive in a 6.5-ounce case that fit a pocket, played for up to 10 hours, and went on sale on November 10, 2001, for $399.
The quiet advantage was FireWire, which Apple said could load an entire CD in under 10 seconds, so filling it was no longer a chore. Pair that with the scroll wheel and you have the design that the rest of this list either led up to or reacted against.
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IPod Mini
The iPod mini is where the iPod became a fashion object. Announced in January 2004, it squeezed the original's 1,000 songs into a 4GB player half the size, weighing 3.6 ounces, in an anodized aluminum body offered in silver, gold, pink, blue or green.
It also brought the touch-sensitive Click Wheel, built for one-handed navigation. At $249 it was not cheap for the capacity, and the trade-off against a roomier hard-drive iPod was real, but choosing your color turned a music player into something personal in a way the white original never was.
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IPod Shuffle
iPod shuffle, first generation, 2005
The shuffle made a virtue of what it left out. Apple pitched it against flash players with tiny displays and complicated controls, then shipped it with no screen at all and built it around playing your songs at random.
It cost $99 for 512MB, about 120 songs, or $149 for 1GB, was smaller and lighter than a pack of gum, and doubled as a USB flash drive. For runners, gym bags and anyone who just wanted something on, it was the most affordable iPod yet, and it made letting the player choose a feature rather than a compromise.
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IPod Nano
iPod nano, first generation, 2005
The nano showed how fast flash memory had caught up with hard drives. Thinner than a standard pencil and weighing 1.5 ounces, it still had a color screen and held up to 1,000 songs in its 4GB version, for $249, with a 2GB model at $199.
Set it beside the iPod mini from the year before and the leap is obvious: similar capacity in a fraction of the thickness, with no spinning drive to worry about. It is the point where a full-featured player became something you could forget was in your pocket.
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Zune 30
Microsoft's answer to the iPod arrived on November 14, 2006, with a 30GB drive, a bright 3-inch screen, a choice of black, brown or white, and a price of $249.99, essentially the same as Apple's 30GB iPod.
Its real idea was social. Wireless Zune-to-Zune sharing let you send a full-length song to a friend's player nearby, and they could then listen to it up to three times over three days. Those limits made the feature feel cautious, but it pointed toward music passed between people rather than synced from one computer, and it gave the iPod a rival with a genuinely different idea. If you want one today, the brown finish is the most distinctive of the three.
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SanDisk portable media players
SanDisk Sansa Clip, 2007
The Clip is the strongest case that the best player of the iPod years did not have to come from Apple. It arrived in the fall of 2007 at $39.99 for 1GB or $59.99 for 2GB, measured about 34 by 54 by 10 mm, weighed around 25g, and packed a small OLED screen and an FM radio. In one review it ran for close to 14 hours.
Unlike the screenless shuffle, it showed you what was playing, and later Clips added FLAC support, a welcome extra for anyone who cared about file formats. For anyone who wanted a cheap player to clip on and forget, it was the quiet favorite.
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IPod Touch (1st generation)
The iPod touch is where the dedicated music player started turning into something else. Announced in September 2007, it was 8 mm thin, used a multi-touch interface on a 3.5-inch widescreen display, and was the first iPod with Wi-Fi, which let you browse and buy from the iTunes Wi-Fi Music Store without a computer.
It played up to 22 hours of audio and started at $299. Everything on this list before it was built to hold music you had already gathered. The touch let you fetch it from the air, which is why it makes a natural end point: the next step was the phone in your pocket doing the same job.
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