(Also, as an aside, certain stars simply love being in music videos and have racked up three or four appearances in total — but that is another story entirely.)
A very late '90s Zooey Deschanel appears in the very late '90s Offspring song, "She's Got Issues," as the aforementioned girl who has, um, issues. Thematically, the song is pretty similar to its massive hit, "Self Esteem," the redheaded Deschanel is a Katy Perry prototype, plagued by hallucinatory cartoons, a lame job, and some pretty extreme boot-cut jeans. If this is what constitutes as "issues," then, we'll be damned.
Anna Nicole Smith in Kanye West's "The New Workout Plan"
Before he was making over Kim Kardashian's wardrobe, Kanye West was enlisting Anna Nicole Smith to help ladies "get right for the summer." (Apparently, once upon a time, West had a sense of humor. Bonkers.) The wobbly enthusiasm of Anna Nicole is oddly surreal, and a hilarious second cameo by Tracee Ellis Ross pushes the whole thing over the top. What's that jacket,
(Also, the breakdown at the end of the song is still one of the hottest things he's ever done.)
Mila Kunis in Aerosmith's "Jaded"
Aerosmith has featured Jessica Biel, a pre-famous Alicia Silverstone, and front man Steven Tyler's daughter, Liv, but we have a soft spot for Mila Kunis in "Jaded." The video has Steven Tyler and Co. acting as a sort of house band for what appears to be a Tim Burton movie or a leftover scene from Moulin Rouge. Mila Kunis is presented with an assortment of wonders, but she doesn't care, because she is jaded. Like the song title. Bam.
Robert Downey Jr. in Elton John's "I Want Love"
This isn't just any cameo. This appearance by Robert Downey Jr. in 2001 marked his first gig after cleaning up his party-boy act and becoming the grown-up version we love today. The director of the video reportedly shot 16 takes, but ultimately used the last one because of RDJ's relaxed composure. Maybe having to sing "a man like me is dead in places" over a dozen times felt like a little bit of therapy.
Natalie Portman in Devendra Banhart's "Carmensita"
It was after appearing in the Bollywood-esque video for "Carmensita" that Natalie Portman started dating hippie folk-rocker Devendra Banhart, but their oddball relationship didn't last long. While their love may have faded, we'll forever have the memory of Portman smiling gamely at Banhart as he sings in Spanish.
Keanu Reeves in Paula Abdul's "Rush, Rush"
Keanu Reeves was a well-known quantity at the time "Rush, Rush" debuted — it was after Bill and Ted but before Point Break — but that didn't diminish his performance in this Rebel Without a Cause-inspired video. That hair, however, didn't age well.
Nicole Kidman in Pat Wilson's "Bop Girl"
We won't blame you if you've never heard of '80s Australian pop singer Pat Wilson, as she never really achieved the same level of stardom as some of her American contemporaries. Her single "Bop Girl," however, did peak at #104 on the Billboard pop chart, but not thanks to an appearance by a 15-year-old Nicole Kidman in the music video. It was Kidman's first on-screen performance and certainly her frizziest.
Zach Galifianakis in Fiona Apple's "Not About Love"
Fiona Apple's "Not About Love" off of her third album Extraordinary Machine is a low-fi, handheld piece of weirdo verité cinema, except Zach Galifianakis lip-synchs all of Apple's lyrics. He also minces around and shoves his hand in her face more than once, making us wonder why she was in love with him in the first place.
Norman Reedus in Björk's "Violently Happy"
The Walking Dead star accompanied Björk and a cast of crazies in her video for "Violently Happy," in which Reedus et al dance with scissors and teddy bears in a padded room. You know, because the '90s.
Angelina Jolie in Meat Loaf's "Rock 'n' Roll Dreams Come Through"
If one must rank Angelina Jolie's best early roles, the top picks would be Hackers, Gia, and the video for "Rock 'n' Roll Dreams Come Through" in that order. That's not to say it's bad — it just has a very unbalanced lip-pout-to-aging-rocker-on-a-hog ratio. Jolie worked with what she was given, and her bewildered runaway is tops. Watch out for exploding jukeboxes!