Ask HN: What 1980s/90s-era shareware did you purchase?

DSZ - Zmodem (Chuck Forsberg) WinRAR 4DOS PKARC

TheBat! - a pretty slick email client for the late 90s

Not Shareware exactly, but once I started earning money in the mid 90s, I purchased physical copies of Slackware on CD-ROM to support the distro that taught me Linux. It was also much more convenient than downloading dozens of floppies from ftp.funet.fi or whatever FTP server I was using at the time. As for my Amiga and C64 days, I was too young to have a lot of money, and piracy was rampant in Europe, where I lived. Even if I had wanted to pay I wouldn't have known how to send money overseas.

Doom, Decent, Hexen, Quake, and KidPix. Everything else was purchased full price (Marathon, Photoshop, MS Flight Simulator, Corel Draw, Word Perfect, Compuserve). There was other software but that was mainly it in the late 80s/early 90s. Mac kid until 91 or so. Somewhere around 92 is when we got our first windows machine and I discovered Id Software.

By mid-90s we had IRC and the wonderful Wild West that DCC brought. By late 90s we had P2P services like Napster and LimeWire.

  - Commander Keen, Wolfenstein 3D, Doom, Decent
  - Telix and OS/2 terminal software for modems
  - PKZip and other archivers
  - Composer 669 -- 8 channel tracker on a 386 using flat protected memory
  - Megaroids -- Asteroids clone for Atari ST
  - Kedit -- large-buffer text editor for OS/2
  - DeScribe -- word processor for OS/2

Of all the games the Decent series was my addiction, got the flight stick/throttle and just couldn't get enough of being almost lost in 6-DoF trying to stay alive! This might have been a shrink-wrap game though, can't recall.