A local production of the musical “Hairspray” got us thinking of some of our favorite TV and movie characters who cross gender lines in dress. This List is not a drag!
10. The trio in “To Wong Foo, Thanks for Everything! Julie Newmar”
Noxeema Jackson (Wesley Snipes), Vida Boheme (Patrick Swayze) and Chi-Chi Rodriguez (John Leguizamo) take off on a cross-country road trip in an old school Caddy and hijinks ensue. It’s kind of like “Thelma and Louise,” only not super depressing.
9. Terry Griffith in “Just One of the Guys”
In this classic ’80s teen comedy, Terry feels sexism is in play at her high school newspaper so she dresses up as a guy and writes for a rival high school. The lengths we journalists will go to get the story.
8. Hedwig from “Hedwig and the Angry Inch”
This rock ’n’ roll musical is a modern classic in our books, thanks to the titular character and his titular inch (the result of a botched sex change). Also, try to listen to “The Origin of Love” without tearing up.
7. Dean Pelton from “Community”
Dean Pelton (Jim Rash) dresses up in many outfits, and not all of them are technically cross-dressing. Still, when he brought out a costume that was both man and woman, he took it to another level — he had to go to the bank that day.
6. Joe and Jerry from “Some Like It Hot”
What’s the best way to escape the mob after witnessing Saint Valentine’s Day Massacre? If you’re Joe (Tony Curtis) and Jerry (Jack Lemmon), you dress up as women to join an all-girl band and hang out with Marilyn Monroe.
5. Babs Johnson in “Pink Flamingos”
Divine was pretty much John Waters’ muse, and we’ll take her in Waters’ most over-the-top trashiest movie — which pretty much makes it the most over-the-top trashy movie ever. Take that, Middle America.
4. Ed Wood in “Ed Wood”
One of Johnny Depp’s best performances, the “world’s worst director” and his predilection for dressing in women’s clothing were handled sweetly in what may be Tim Burton’s best film.
3. Mrs. Featherbottom in “Arrested Development”
Tobias Fünke’s well-intentioned desire to see his family came in the form of a Mrs. Doubtfire/Mary Poppins parody that will live in pop culture infamy.
2. Dorothy Michaels in “Tootsie”
Michael (Dustin Hoffman) can’t get acting jobs because he’s difficult to work with. So he disguises himself as Dorothy in one of the great rom-coms of all-time thanks to a great cast and an indelible performance by Hoffman.
1. Dr. Frank-N-Furter in “The Rocky Horror Picture Show”
Dammit, Janet, Tim Curry’s “sweet transvestite from Transexual, Transylvania” is an icon.