10. Katy Perry: "Smurfette," The Smurfs Obviously, it's hard to comment on exactly how weird Perry's appearance in this upcoming live-action/CGI adaptation of the popular children's TV series will be, since the movie isn't slated to be released until next year. However, if Perry's commentary on the role--she mentioned she wasn't allowed to watch the show when she was a kid because her parents felt Smurfette, the lone female character, was probably "slutty"--is any indication, it's going to be fucking bizarre.
9. Will Smith: "Will Smith," The Fresh Prince of Bel-Air Since Will Smith's role in The Fresh Prince of Bel-Air catapulted him into an acting career from which he never turned back, a lot of people probably don't even remember that Smith was a rapper in the '80s--a really successful one; his second album with DJ Jazzy Jeff, He's the DJ, I'm the Rapper, went multi-platinum. But yeah, as hard as it is to believe, Will Smith was once a rapper. You can tell because the series theme--penned by Smith--is probably the most memorable TV theme song ever (Cheers aside).
8. Elvis Presley: "Scott Heyward," Clambake For years, Elvis Presley demanded an astounding (for the time) salary of $1 million for every movie he made; Clambake was the last of his films to garner such a salary. Both typical and outstanding in his filmography, Clambake is almost sublime in its lameness, from the theme song (lyrical sample: "Clambake / Gonna have a clambake") to the plot, which is established within five minutes. Featuring an almost-but-not-quite-yet fat Elvis at his most irrelevant, Clambake represents a turn toward precipitous decline in the King's career.
7. Britney Spears: "Lucy Wagner," Crossroads It's not that weird that somebody would cast Britney Spears in a teen movie. Consider: At the time (2002), Spears was at the height of her career, with "...Baby one More Time" and "Oops...I Did it Again" (she loves ellipses, apparently) behind her and great things ahead. But it is weird, watching Spears so young and innocent, to consider where her life almost immediately went from there--who'd have thought K-Fed would turn out to be the better parent? And the fact that Dan Aykroyd is in it--well, sigh.
6. Ice Cube: "Nick Persons," Are We There Yet? What's weird is that Ice Cube, former frontman of pioneering gangsta rap outfit Niggas With Attitude and the man responsible for "Fuck tha Police," is now a G-rated commodity. What's weirder is that Are We There Yet? capitalizes on that incongruity, casting the Cube as a chip-on-the-shoulder gangsta type who hates kids and yet cares for two of them out of ruthless self-interest and learns some important life-lessons in the process. You cannot watch this movie without feeling sad.
5. Ice T: "Scotty Appleton," New Jack City Similarly to the other Ice, the incongruity of Ice-T's role comes from his early image as a gangsta. To be fair, T's infamous single "Cop Killer" didn't come out until 1992--a year after he played an undercover cop in New Jack City, but still, you have to admit, pretty weird (notably, after "Cop Killer" he went back to playing cops in Law and Order: SVU). Nevertheless, a surprisingly solid performance from T and a supporting cast that includes Wesley Snipes and Chris Rock make this film a classic.
4. Prince: "The Kid," Purple Rain Probably because the movie was conceived as a marketing vehicle for Prince's music--albeit a tasteful one with an artistic vision, some would argue--it essentially functions as a ninety-minute theatrical music video (think Lady Gaga times 10). The plot is secondary, the acting is pretty terrible, and Prince basically plays his inscrutable self, with plenty of stage time. It's already weird, but viewing it from the lens of the intervening 26 years and knowing how Prince would go on to become a mind-warping self-parody makes it positively otherworldly.
3. David Bowie: "Jareth, the Goblin King," Labyrinth David Bowie plus a George Lucas film featuring muppets: Could there possibly be anything weirder? Gratuitous weirdness aside, this movie is actually pretty awesome, and rather than detracting from the film, Bowie's performance augments it. His creepy-yet-introspective portrayal of Jareth, the Goblin King, is spot on. And the soundtrack. Seriously, how good is it?
2. Michael Jackson: "Scarecrow," The Wiz Before the multi-platinum success of Thriller, Michael Jackson experimented with a short acting career that began and ended with The Wiz, a blaxploitation spinoff that refurbished The Wonderful Wizard of Oz with an all-black cast (including Diana Ross and Richard Pryor) and an urban mythos. Jackson played the Scarecrow, which, in this version, is made out of trash. Not weird enough for you? Check out Jackson singing "You Can't Win" while appearing to be lynched and surrounded by dancing bird-monkeys.
1. Ringo Starr: "Larry the Dwarf," 200 Motels Though he also provided narration for the 80s-era Thomas the Tank Engine series and, of course, participated in the Beatles' film oeuvre, Ringo Starr's acting career was about as limited as his drum fills. But that doesn't make his appearance in Frank Zappa's 1972 film 200 Motels any less memorable. Playing "Larry the Dwarf," who is "large for a dwarf" and also, for some reason, impersonating Frank Zappa, Starr manages to make an impression among a cast of notables--like Keith Moon, Zappa himself, and Donald Duck--in a movie already impressive for its sheer incoherence. Seriously, the film makes about as much sense as the trailer.
