1984. Before I was 16, I was limited by my allowance, but this is what I had.

Jethro Tull - Aqualung
Jimi Hendrix - Smash hits
The Cars - The Cars
Black Sabbath - Greatest hits
Pink Floyd - The Wall
Pat Benetar - In the heat of the night
The Rolling Stones - Rewind
Wings - Greatest Hits
Bob Dylan - Live at Budokan
Elton John - Greatest hits
Tom Petty - Damn the torpedoes
Cream - Strange brew best of
Deep Purple - Deepest Purple best of
Guess Who - best of
Billy Idol - Rebel Yell

I was given a Bolla wine gift box (without the wine). It was perfect for my cassettes.

Never had a Walkman, but listened to all the tunes below, then and now.

I was mowing laws the summer I got a Walkman. My go-to cassette was Motley Crue's Too Fast For Love, which is still in heavy rotation on my iPhone now. Always lots of VH, Iron Maiden and Loudness too, both then and now.

Mostly Grateful Dead bootlegs. But I always put on Yes's Going for the One album while skiing at Sugar Bowl. Good times.

Pretty much only used mine when skiing and had several mix tapes of azz kicking R &R as well as the usual '60's fare - Doors, Stones, Cream, Tull, et'c. A few mellow tapes just in case. Fanny pack or backpack with tapes. Next to last Walkman died at Alta with a full frontal plant with it in my chest pocket. BIG chest bruise and lots of parts and shards.
Still use my ipod and quickly appreciated more music in a much smaller package without hauling tapes. Plus better sound. Many more mellow cruising tunes these days.