My portable music player lineage.
Nomad MuVo (Creative, 2004)
Ah, when 30 songs seemed like a luxury. Being able to plug in via USB and drag+drop from my Windows PC was the main selling point here.
CD Walkman D-EJ001 (Sony, 2005)
My laptop had a CD burner and CD-Rs were insanely cheap, so I burned tons of custom playlist CDs for busrides to/from high school, in addition to backing up a ton of data on CD-R too (mostly BitTorrented anime).
Zune 1st Gen (Microsoft, 2007)
What a wonderful device. Version 1.0 of the Windows software was a mere Windows Media Player reskin, but 2.0 onwards had a industry-leading interface. 3.0 introduced custom apps and XNA publishing, and I loved tinkering with the SDK and C# as a teen hobbyist.
ODROID-S (Hardkernel, 2012)
Given as a gift for helping with a South Korean manufacturer's website, this served me well when I moved to Boston in the ~2 months before I finally got a smartphone.
Smartphones (Google's Nexus & Pixel lines, 2012-present)
Once you get cellular connectivity and apps, it's hard to go back. Streaming has been great too (I enjoy YouTube Music Premium).
My biggest MP3 desires back in the day...
iPod Video (Apple, 2004)
Mowed so many lawns saving for this... But I guess other things came up instead.
iPod Shuffle 1st Gen (Apple, 2005)
The definition of futuristic. Was in love after seeing this at my first YGO tournament.
Zune HD (Microsoft, 2009)
Despite debuting during my hype for Android smartphones, the Zune HD called to me. Amazingly designed even a decade later.