In addition to being Spider-Man's first big-screen adventure, director Sam Raimi's 2002 classic also featured many famous faces in small or cameo roles. Ever since 2012's release of The Avengers broke all kinds of box office records, the Marvel Cinematic Universe has reigned supreme at or near the top of the theatrical charts nearly every year. Before that though, it was a trio of late-1990s/early-2000s Marvel-based movies that served to set the stage for the company's coming dominance.
The first was 1998's Blade, which was a huge financial success despite being R-rated, and helped make Marvel movies seem cool again. Then in 2000, the first X-Men movie was released by Fox, also becoming a huge hit, and spawning one of the longest-running superhero movie franchises to date. Completing the trio was Raimi's Spider-Man, which made even more money than the other two, earned great reviews from both fans and critics, and became a pop culture phenomenon.
While the cast of Tobey Maguire, Kirsten Dunst, James Franco, and Willem Dafoe will always remain towering figures in the memories of Spider-Man fans, Raimi's first Spidey movie also featured lots of other recognizable faces. Some of them were already famous, while others were still a few years away from breaking out as stars.
Joe Manganiello (Flash Thompson)
Long before he was Zack Snyder's Deathstroke, or the most muscled-up celebrity Dungeons and Dragons player, Joe Manganiello played the role of Flash Thompson in Spider-Man 2002. He began the film as Mary Jane's boyfriend and a jock who bullied Peter Parker. That all changed when Peter acquired his powers and struck back, sending Flash flying. Flash would later appear briefly in Spider-Man 3, attending the funeral of a fallen, but redeemed, Harry Osborn.
Ted Raimi (Hoffman)
Sam Raimi often includes his brother Ted Raimi in his movie and TV projects. In Spider-Man, Ted plays Hoffman, the top yes-man to Daily Bugle boss J. Jonah Jameson (J.K. Simmons). He's supremely dedicated but usually mistreated. He remained loyal though, still working for Jameson onscreen in Spider-Man 2 and Spider-Man 3. Since Raimi is part of the MCU now, and so is Simmons' Jameson, a Hoffman MCU cameo could be gold.
Bruce Campbell (Ring Announcer)
Bruce Campbell, who became an icon due to playing Ash Williams in Raimi's Evil Dead trilogy, actually cameoed as three different characters in the Spider-Man trilogy. In the 2002 original, Campbell plays the ring announcer at the pro wrestling show Peter participates in to win some cash. Memorably, he comes up with the Spider-Man name in-universe after being dissatisfied with the name Peter tells him to say. One wonders if Campbell will cameo in Raimi's Doctor Strange in the Multiverse of Madness too, one of many upcoming MCU movie and TV projects.
Elizabeth Banks (Betty Brant)
While not one of his high school friends like in the MCU, Elizabeth Banks' Betty Brant - secretary to Jameson - still made an impression in her brief appearances in Spider-Man 2002. Banks' star wouldn't really begin to rise until the mid-2000s, but her interactions here with Peter are fun and flirty, and her exchanges with Jameson are also amusing. Banks returned as Brant in Spider-Man 2 and 3, where it became more and more obvious that she was romantically interested in Peter.
Randy Savage (Bonesaw McGraw)
Perhaps the most famous cameo role in Spider-Man 2002 belongs to late pro wrestling legend Randy "Macho Man" Savage, who played Bonesaw McGraw, the champion wrestler who expects to make mincemeat out of Peter inside a cage. Little does he know that there's more to Peter than meets the eye, although Savage's now-MCU-canon Bonesaw himself would've surely appreciated Peter's high-flying offense. It's a memorable scene, watching Peter use his powers to win, and illustrates just how big a pop culture footprint Savage left behind.
Octavia Spencer (Check-In Girl)
Long before Octavia Spencer became a household name thanks to movies like The Help and Hidden Figures, she played a bit role in Spider-Man 2002. She handles the check-in desk at the pro wrestling show and is understandably incredulous when a guy as small as Peter Parker wants to get in the ring. In hindsight, at least in a roundabout way, if Peter had listened to her warnings against wrestling, the unfortunate events that led to Uncle Ben's death wouldn't have been set into motion.
Macy Gray (Herself)
Primarily known as a music star, Macy Gray made a cameo as herself in Spider-Man 2002, performing at Oscorp's Unity Day Festival, which of course sees The Green Goblin show up and vaporize some folks, before targeting Mary Jane. Gray had a song on the movie's soundtrack, so it makes sense that they would call her to make such a cameo. Gray has actually appeared in a surprising number of movies for someone who isn't a full-time actor, including Training Day, Scary Movie 3, and Idlewild.
Lucy Lawless (Punk Rock Girl)
Lucy Lawless, who of course gained fame starring in the Sam Raimi-produced Xena: Warrior Princess, makes a quick but funny cameo in Spider-Man 2002. Following Spider-Man's arrival in New York City, various residents are surveyed by the news about their opinions of the hero. Lawless' punk rock character is for Spider-Man since a "guy with eight hands" "sounds hot" to her. It's far from a Xena and Spider-Man crossover, but it's the closest anyone's likely to get on film.
Stan Lee (Man in Fair)
The late Stan Lee of course needs no introduction for just about anyone, as after creating or co-creating many of Marvel's most iconic characters, he went on to become a pop culture icon in his own right. Lee's cameos throughout the MCU's Infinity Saga will always be legendary, but his first Marvel movie cameo actually came in Sam Raimi's Spider-Man. Appropriately, the web-slinger's co-creator appeared during The Green Goblin's attack on the festival, with Lee running over to save a girl from being crushed by falling debris.