In the 90s i used perhaps half a dozen pieces of shareware with any regularity but only purchased three (in no particular order):
1) TheDraw - an ANSI/ASCII art editor, which i briefly used for creating animated screens for use with dial-up BBSes.
2) 4DOS/4NT was a command.com replacement for DOS/Windows which offered features such as the command-line editing available in all modern shells.
3) DOOM, which my two housemates chipped in to help buy. We played the hell out of it, multi-player on two 486/66's connected with a serial cable.
All of the purchases arrived via snail-mail, with TheDraw and DOOM on floppy disks and 4DOS on a CD. A couple weeks after buying it, one of my housemates took the DOOM disk(s?) to his father's place and ended up infecting it with a virus.
What shareware, if any, did you purchase back in the day (and what did you use it for)?
Edit: there was a 4th: WinRCS was a Windows front-end to the RCS version control system. It didn't get much use but it was my introduction to source code control.