This shirt comes from season 5 episode 5 “Treehouse of Horror IV” specifically the short “Terror at 5 and a half feet”. The Treehouse of Horror episodes have always been among my favourite episodes as they spoofed some great classic tales and gave the writers some creative freedom as the shorts are not canon to the Simpsons universe. This specific short mimics The Twilight Zone’s “Nightmare at 20,000 feet” which was originally released back in 1963 and starred William Shatner. Interestingly enough, the Twilight Zone episode is based on a short story written in 1961. But anyways before I go too far down that rabbit hole, in the episode Martin is shown wearing a “Wang Computers” shirt. As hilarious as that company name is, it was an actual electronics company founded in 1951. It attempted to compete with IBM, essentially lost, and was absorbed by a Dutch company in the 90s. But again, that’s not a rabbit hole I’ll go any further down for now.
Here’s the link to the product as a sticker, but you can view the design on multiple items if you’re interested.
