The show was finally canceled when Aaron Sorkin decided to concentrate on his other show, The West Wing (1999). Despite low ratings on ABC, it got several attractive offers to continue on cable TV. All the deals included Sorkin as a writer, but Sorkin declined.
Clark Gregg was offered one of the lead roles. He had to turn it down because he was working on the pre-production of What Lies Beneath (2000). Gregg ended up playing the recurring role of The Stranger.
The tapes and decks used on the show are U-Matic (aka 3/4") format, which would have been very out-of-date in the late 1990s. At the time, the standard would have been Betacam. U-Matic equipment looks very much like Betacam equipment, and would have been much cheaper, especially for use as a prop.
During one episode, Dan shakes writer's block by reminding himself why he got into writing in the first place - to impress women. Josh Charles, who plays Dan Rydell, was also in Dead Poets Society (1989) in which Josh's character wrote poetry also to woo a woman.