Some fans consider Zoolander one of Ben Stiller's best goofball comedies. The movie presents an original comedy taking place in the elite world of fashion. The film pulls audiences into the industry thanks to some of its famous faces including Tommy Hilfiger and Donatella Versace.
Characters like Derek Zoolander and Hansel MacDonald are meant to be some of the most famous models in the universe of the movie. As such, recognizable celebrities appear in cameos and help develop their notoriety as stars by singing their praises. Over two dozen celebs make cameos, but the best appearances are made thanks to the memorable lines these entertainers say, and the interesting conflicts they contribute to.
Lenny Kravitz
Perhaps the first memorable conflict in Zoolander comes during the ceremony at the beginning of the film. Derek believes he is a shoo-in for Male Model of the Year. However, he seems to have a misunderstanding after Hansel is crowned the victor, and Derek heads to the stage to accept the award anyway.
Lenny Kravitz appears in this sequence. He introduces the nominees before Hansel and Derek's career segments are presented. When Derek comes on stage, Kravitz is forced to whisper into his ear and tell him what he's missed. He directs him toward the massive screen behind him declaring Hansel the winner.
Fred Durst
Many fans might say one of the most memorable sequences in Zoolander comes when Derek is hypnotized at a "day spa." He is given instructions to assassinate the Prime Minister of Malaysia during a fashion show. During the process, Jacobim Mugatu, one of Will Ferrell's funniest characters, prepares Derek with a mock runway.
He warns Derek not to be distracted by "the beautiful celebrities," as cardboard standees of a few begin to appear. At the end of the film, the same real celebs show up during a show. Fred Durst is one of the best cameos because it shows how Zoolander is such a time capsule, putting relevant entertainers of the time on display who have since moved on to different things, like Durst's transition to film director.
Tyson Beckford
Tyson Beckford is one of the most prominent male models featured in Zoolander. He appears during the most notable conflict between Hansel and Zoolander, during the infamous walk-off sequence. Part of the gag with the scene is Hansel and Derek having break corners with "coach" figures as if they are in a boxing match.
Beckford acts as Derek's coach and hype man during the competition. When Hansel begins his moves, Beckford can be heard saying, "play school, baby." He rubs Derek's shoulders and gets him refreshments. Perhaps Beckford's funniest moment is when he warns Derek to not emulate Hansel's underwear disappearing trick, and his reaction when Derek doesn't pull it off (literally).
Natalie Portman
The opening sequence in Zoolander showcases the lion's share of celebrity cameos. Several notable members of the fashion industry and Hollywood elite are put on display singing the praises of Derek Zoolander. However, some appearances are more memorable than others.
Natalie Portman showcases one of the more notable cameos from the film's introduction. She spouts funny lines and implies she wants to date the coveted model. She says Derek might be too good looking, which would be the main "deterrent in, you know, considering . . . a relationship."
Cuba Gooding Jr.
Zoolander may not give Cuba Gooding Jr. one of his best roles, but he gives the movie a funny cameo. He presents one of the other more memorable appearances in the film's opening sequences. While some celebrities only say a short phrase about Derek, the camera seems to linger on Gooding Jr.'s part.
Cuba Gooding Jr. praises Derek's look in his appearance. He spouts what appears to be an off-the-cuff improvisational line, saying his hair is "almost like the new afro for the white man, but it's beautiful." It cuts between the line and Derek showing off his eccentric signature hairdo.
Fabio
Fabio is showcased in Zoolander early on. He appears after the opening sequence, as a fellow model at the ceremony the main characters attend. He is shown accepting an award before Male Model of the Year is awarded.
Fabio's lines are funny, thanking the audience for naming him the best "actor slash model, and not the other way around." His moment is made more memorable by the film's cuts to Derek's reaction. He rolls his eyes and claps unenthusiastically.
Winona Ryder
Winona Ryder gives Zoolander one of its richest cameos. She is showcased for more than most of the film's cameos, talking to Derek at a party as if the two are old friends with romantic chemistry. She praises Derek for his foolish actions after losing his award to Hansel, underscoring the film's running gag of Derek's massive popularity despite his obvious flaws.
She calls his actions "so courageous," seemingly deep in conversation. Derek responds that he has to pee but that he'd really like to "continue talking about this conversation when [he comes] back."
Billy Zane
Fans probably remember Billy Zane's cameo from Zoolander, as he presents funny lines and is referenced by multiple characters. Just before Derek and Hansel's walk-off, Billy and Derek have a friendly exchange. When Hansel and Derek confront each other, Billy gets more involved.
As tensions rise when Hansel and Derek begin to argue, Billy Zane hands his drink to another partygoer and stands behind Derek to support him. He warns Derek not to perform in the walk-off. Hansel tells Derek, "listen to your friend Billy Zane, he's a cool dude." When he tries to warn Derek further after the challenge is announced, Derek cuts him off saying, "put a cork in it, Zane!"
David Bowie
David Bowie isn't credited for his role in Zoolander. However, it is hard for audiences to argue that he doesn't present the most memorable cameo in the movie. As the infamous walk-off sequence begins, Hansel asks the crowd who will judge it. Bowie emerges and offers to do the job as his name flashes on the screen.
The audience gasps and Bowie gives the two instructions for the competition. He is then presented in several reaction shots. Perhaps Bowie's most notable non-speaking moment comes, like Tyson Beckford, when Derek is defeated in the sequence's final moments.