1.
2. 1979 (TPS-L2)
This is the first Walkman ever made and is widely regarded as the first ever portable music player. Everything that came afterwards came from this. The TPS-L2 cost around $200 and despite the high price, did really well.
One really cool feature was the Walkman came with two headphone jacks, a microphone, and a button to lower the music so people could share an Walkman and talk during the song. Though it seems sort of strange now, these were included because Sony co-chairman Akio Morita was worried that “it would be considered rude for one person to be listening to his music in isolation.” HA!
Sony hadn't really got the naming down at that point, early versions just had "stereo" on them. When the name Walkman was suggested, Sony was worried that it sounded too Japanese for native English speakers, so the player was named "Soundabout" in English-speaking countries, and "Walkman" everywhere else. The U.K. and Sweden were the exceptions: they called the device "Stowaway" and "Freestyle," respectively. Obviously "Walkman" eventually stuck, and for good reason. I'm not convinced that "Stowaway" would of had the same staying power.
If you had this version, you'd be listening to The Sugar Hill Gang's "Rapper's Delight”
3.
4. 1981 (WM-1 and WM-2)
Oddly enough, the WM-2 ( Also known as "Walkman II") actually came out before the WM 1. It replaced the TPS-12 as the smallest cassette player, being only slightly bigger than an actual cassette. Despite being more expensive ($140) than many of the previous models, the WM-2 was the best-selling of all the versions. It was similar to the first Walkman, retaining the dual headphones and mic, but everything was made a little bit more compact.
The WM-1 was the first of the models purposefully priced down to help make the Walkman more accessible and as a result, was a sort of a step back technology wise. This was basically a bigger, cheaper Walkman than the WM-2. While the cost was still pretty high at $100 dollars, it helped open up the market and paved the way for the Walkman's cheapest models.
If you had this, you'd be listening to the Dead Kennedys' “Too Drunk To f*ck.”
5.
6. 1982 (D-50, WM-3 and WM-7)
The first ever Discman, then called "compact disc compact player" was put out 1982, just after the release of the first ever CD. As you probably remember, the Discman had no mechanism to stop the CD skipping, so walking with it was a challenge. Also, batteries weren't built into this model, so you had to get a separate battery case which bulked the Discman up and added considerable weight.
Two Walkmans were also released this year (check them out below) and were pretty similar to other models, with a slight change: for the first time the play button (which had previously been listed as "listen") was changed to "play."
I think it's necessary at this point to take a minute and think about how both the Walkman and the Discman didn't fit in people's pockets. The Discman had a place to attach a shoulder strap so you were essentially carrying around a stereo, while Walkmans had a clip that you attached to your jeans which Sony marketed as an ill-fated fashion statement.
If you had this, you'd be listening to Michael Jackson's “Thriller.”
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11.
12. 1983 (WM-10 and WM-4)
The WM-10 was the smallest cassette player ever made. It was actually smaller than a cassette—you had to expand it to insert and listen, so it functioned more as a headline grabbing, "look how small we can make things" product for Sony than an actual practical music player. On the complete opposite end of the spectrum, the WM-4 was pretty massive: it needed four (four!) AA batteries. In comparison, the WM-10 survived on just one). However, its size worked in the WM-4's favor, as the extra power made it one of the loudest models.
If you had this, you'd be listening to Talking Heads' "This Must Be The Place."
13.
14. 1984 (WM-22 and WM-DD2)
1984 was a big year for the Walkman; Sony put out six different versions. Rising from the chaff was the WM-22, the first cheap Walkman, on the market for about $40. Up until now, the device's cost had mostly been in the hundreds, but this cheaper model helped solidify Sony's place in the market and made Walkmans go mainstream. It also came in a lovely blue shade.
As an aside, the WM-DD2 looks like one of the Walkmans they were putting out in the 2000s. The $40 model seems so strangely retro in comparison.
If you had this, you'd be listening to Run DMC's “It's Like That.”
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18. 1985 (WM-75 and WM-W800)
Marketed as the "sports Walkman," the WM-75 came in banana yellow and was waterproof, complete with rubber openings and waterproof controls. To add to the nautical theme, they added a little porthole through which you could watch the cassette turn. Though "Pretty Woman" most likely used a later model, Sony clearly had this sort of chilling in mind when they invented this model. They later went to make another version that actually floated which I really think should be revived.
In the same year, Sony introduced it's first twin tape deck model, the WM-W800, which obviously was made for old school pirating (read: copying your mate's cassettes).
If you had this, you'd be listening to The Jesus and Mary Chain's "Just like Honey."
19.
20. 1986 (WM-3000)
In 1986 Sony released the Walkman-3000 as part of the "My First Sony" collection, which included a boom box and walkie talkies, among other things. This red Walkman came with safety features such as rounded edges and a volume control so kids wouldn't damage their hearing.
The highlight of the 'My First Sony' series was the unabashedly obvious attempts at indoctrinating youth into the Sony brand: the trailer for the series has kids singing about loving their first Sony's, and ends with a very disconcerting “it won't be your last.”
If you had this, you'd be listening to "My First Sony's" incredibly creepy theme song.
21.
22. 1987 (WM-F107)
While other models were released this year, the Solar Walkman is really the only one worth discussing. The idea is too sick: you couldn't forget your charger because your charger was the sun!
Granted, the design wasn't perfect. Namely, it took time to charge. The radio ran with minimal sun charging but to listen to the cassette, the Walkman had to be left out in the sun a couple hours at least. To counteract this, they included an extra battery-powered option. So in actuality the solar mechanism was mostly used to power the radio.
The idea of solar tech is still interesting, and beginning once again to gain steam. A quick Google search brought me to a solar-powered laptop, so obviously Sony was way ahead of its time.
If you had this, you'd be listening to The Smiths "Girlfriend in a Coma"
23.
24. 1988 (WM-B39, WM B-10 and WM-B52)
In 1988 Sony released three Walkmans with some interesting features. The WM-B52 built on the Solar Walkman from the previous year with a Walkman that had a solar alarm clock intended as a tanning aid. Understandably, it had a few mechanical difficulties. Only the clock was run on solar: the alarm function was battery-powered, and the cassette player was mechanically separate to the alarm. This aspect most likely caused a couple sunburns. If you were listening to a cassette, you wouldn't be able to hear the alarm.
The WM-B10 came in various colors and introduced the tag line “An essential item for modern life. Amazing sound any time, anywhere.” The WM-B39, meanwhile, was the first to feature the brilliantly named "mega-bass" which was designed to improve audio quality on the worst headphones.
If you had this, you'd be listening to N.W.A's “Straight Outta Compton.”