For as much of a fondly remembered, out-of-the-gate success Spider-Man: The Animated Series was during its 1994-1998 run on Fox Kids, the production side of things could not have been more chaotic. Joining the show to replace departing showrunner Martin Pasko, John Semper found himself trying to right a fast-moving ship with an eye toward accurately replicating the feel of classic Spider-Man comics. Even then, airing on broadcast network television left the series to the whims of interests beyond the Fox Network and Marvel Comics alone. There was also a need to keep toy manufacturing partner (and then-recently absorbed Marvel subsidiary) Toy Biz happy by featuring a steady supply of characters in the series suitable for inclusion in the accompanying toy line.
This resulted in the series' infamous decision to feature the Hobgoblin prior to the Green Goblin. After an action figure and deluxe accessory were in production for the 1994 holiday season based on the choice by Semper's predecessor to change the order of their introductions, Semper reluctantly accepted it after meeting with Toy Biz CEO Avi Arad. Their fragile working relationship ultimately came to a head over the inclusion of one character, however. Crafting a storyline that brought elderly, immobile clairvoyant Madame Web into the series, Semper's outline was rejected by Arad, the latter dead-set against the action figure-unfriendly character appearing in the series. Nevertheless, their confrontation had a surprising outcome, one most evident in the toy aisles.
Cassandra Webb aka Madame Web was introduced in 1980's Amazing Spider-Man #210 by Dennis O'Neil, John Romita Jr., Joe Sinnott, Bob Sharen and Jim Novak. Appearing once more by her creators in #216 (O'Neil, Romita Jr., Jim Mooney, Sharen and Novak), she returned during the classic two-part story "Nothing Can Stop the Juggernaut!" in Amazing Spider-Man #229 and 230 by Roger Stern, Romita Jr., Mooney, Glynis Wein and Joe Rosen. Left gravely injured and seemingly no longer possessing either her clairvoyance or knowledge of Spider-Man's secret identity, Madame Web made a final brief appearance in Amazing Spider-Man #239 by Stern, Romita Jr., Frank Giacoia, Wein and Diana Albers. Although the character returned in 1998's Peter Parker: Spider-Man #96 (by Howard Mackie, Norman Felchle, Scott Hanna, Gregory Wright, Richard Starkings and Liz Agraphiotis) and would make regular appearances across several Spider-Man titles thereafter, the five original appearances were all Semper had to draw from for the animated series.
Not that he was intent on bringing a fully accurate page-to-screen representation of the character onto Spider-Man: The Animated Series. Her cameo appearance at the end of the third season premiere, "Doctor Strange," where the Sorcerer Supreme himself referred to "Being watched by someone whose powers dwarf my own" was a solid indication the character would be fairly different from her nominally super-powered comic book counterpart. Voiced by Joan B. Lee, wife of Spider-Man co-creator Stan Lee, Madame Web would recur throughout the season, offering the ominous warning that she was training Spider-Man for an incoming "Horror beyond belief!" Her refusal to assist the Wall-Crawler in locating a missing and presumed dead Mary Jane Watson in the season finale saw him sever ties with her.
With a 65-episode order already locked in for the series, Semper had the luxury of plotting several seasons worth of storylines well in advance for a long game. To that end, the introduction of Madame Web was one piece toward the final season and an abridged adaptation of Marvel's Secret Wars crossover (which itself was originally created in service to a toyline). The arrival of the Beyonder would be the seeming payoff for the earlier warning, even if it didn't completely line up with the reveal the character was working to save the universe. The three-part "Secret Wars" episodes led to a series finale that gathered several alternate Spider-Men to combat a rogue Peter Parker bonded to the Carnage symbiote and seeking multiversal collapse. It was this eventual payoff that convinced Arad of the worth of bringing the character in, even if he remained ever-insistent, as Semper later recounted, he couldn't "Make a toy out of an old broad."
With the January 31, 1998 series finale concluding with Spider-Man and Madame Web venturing forth to recover a cosmically displaced Mary Jane Watson, it wouldn't be very long before Toy Biz went back on Arad's impassioned protestations and introduced Madame Web into 1998's "Sneak Attack: Flip 'N Trap" wave, one of the final releases tying into the animated series. Semper recounted the fight to get Madame Web on the series in a 10th anniversary interview with Marvel Animation Age, noting that the figure became "One of my most prized possessions." He later re-shared the anecdote on social media after Joan B. Lee's 2017 passing, offering credit for the success of the character to her performance.
Despite the shot-in-the-arm gained by her showings on Spider-Man: The Animated Series, Madame Web's return to comics in 1998 saw the character quickly deaged, a status quo all-but ignored in later appearances circa the Civil War crossover. Madame Web was one of several Spider-Man family characters swept up in 2010's "Grim Hunt" storyline, which ended with her giving her powers to former Spider-Woman Julia Carpenter before dying. Later animated series Ultimate Spider-Man featured a composite of the two incarnations of Madame Web portrayed by Cree Summer. Although the in-production Dakota Johnson-starring Madame Web film developed for Sony's adjunct Marvel Cinematic Universe seems to be jumping to Julia Carpenter's Madame Web, it remains a strong possibility that Cassandra Webb herself will make the leap to the big screen in some form or another. After all, stranger things have happened.