Previously: Male comedians in drag, ranked by attractiveness.
No woman, regardless of orientation, can long resist a boyish woman dressed in a well-tailored men’s vest. Whether it was this scene from Just One of the Guys:
Or this scene from Young Americans:
there came a time in your young and vibrant life when you were shocked to alertness by the quick-moving, wicked-smiling presence of a woman dressed as a man on a screen in front of you, and that alertness has lived in your stomach ever since. Let us rank these women now in order of how they won and wrung our eager hearts, because who is there to stop us?
23. Amanda Bynes, She’s The Man. Awful. Just awful. It’s like she’s not even trying. Do you know who is a more convincing boy than this? Vanessa Bayer as Jacob the Bar Mitzvah boy on Weekend Update. Have some respect for the craft.
22. Julie Andrews, Victor/Victoria. It’s a little unfair to put her in the same category as the others, because she does spend a lot of the movie playing a man pretending to be a woman. Nevertheless, a verdict must be reached: not great. Stylish, but not great. Sort of like Fred Astaire’s bloodless twin. I respect the hell out of her, but I do not want to seize her by the bowtie and become one. It’s the eyebrows.
21. Cameron Diaz and Drew Barrymore, Charlie’s Angels. Included mostly because of how good Lucy Liu looks in this shot. Diaz is nice enough, in a slight, anemic, “ah-me-I-was-a-pale-young-curate-then” sort of way. There is something horribly unsettling about Drew Barrymore in drag. He is not un-handsome, but he is not right. Like something very small and very determined is wearing Will Forte as a suit.
20. Rachel Stirling, Tipping The Velvet. Maybe the only actually lesbian character on this list. I regret to inform you that I do not find Nan to be particularly convincing. It’s partly the eyebrows, but that’s not the only drawback. She looks like one of the thousand other soft butches in newsboy caps who were standing outside smoking in front of The Abbey and The Cubbyhole and the Lexington in 2003.
19. Anita Yuen, He’s A Woman, She’s A Man. Perfectly nice, but unremarkable.
18. Ossi Oswalda, I Don’t Want To Be A Man. Perhaps a trifle too round-faced, but exceedingly pleasant. Strangely reminiscent of Dave Foley, who many have noticed looks like Isabella Rossellini when he dresses like a woman; the gender serpent eating its own tail.
17. Keira Knightley, Pirates of the Caribbean II. Just for a few minutes, if I recall, and it wasn’t terribly convincing, but she makes for an enchanting boy. I’ll never understand why she isn’t a bigger lesbian icon, Bend It Like Beckham aside.
16. Alana Austin, Motocrossed. There is not a very good reason for a Disney Channel movie to be on this list; this is a very chaste and heterosexual film about a girl who likes to race dirt bikes, but I watched it every day for an entire summer until obsessively rewatching what I wanted but didn’t understand made me dizzy.
One of the most difficult parts of male drag for women to pull off is the jawline; men have almost no fat in their faces, which I will not criticize them for here. Find the right jawline and you’re halfway there.
15. Imogen Stubbs, Twelfth Night. Almost, but not quite, a Cary Elwes type. A lack of something, although she rolls up her sleeves nicely during the pool scene.
14. Tilda Swinton, Orlando. It grieves me deeply that Tilda Swinton does not rank higher on this list. By all rights she should, this David-Bowie-lookalike shapeshifting gender wraith. By all rights she should be queen and master of this list, sailing it around the midnight seas. But nobody looks their best in a curly ginger wig and a foppish ruff. Only magnificent.
13. Pretty much everyone in the Takarazuka Revue. “A Japanese all-female musical theater troupe based inTakarazuka, Hyōgo Prefecture, Japan. Women play all roles in lavish, Broadway-style productions of Western-style musicals, and sometimes stories adapted from shōjo manga and Japanese folktales.” Second from the right, then all of them, then the second from the right again.
12. Liselotte Pulver, The Spessart Inn. GIRL ROBIN HOOD. GIRL ROBIN HOOD. If there is no part of you that has longed for the warm hands and the light laugh of GIRL ROBIN HOOD, then I do not know what to say to you. The best movies about crossdressing women generally feature rich and lusty-laughed tomboys longing to escape to the freedom of the woods. This is one of them.
11. Mulan, Mulan (live-action and animated). Put a woman in drag, and you please us for a day. Put a woman in drag and then armor, and you have the hearts of the people forever.
10. Park Shin-hye, You’re Beautiful. Everyone in this actively perfect K-drama is so floppy-haired and perfect-skinned and androgynous. It’s a wonderful festival of gender chaos, and she’s the crown jewel. If festivals had jewels, I guess.
9. Milla Jovovich, The Messenger. Overcame a disastrous haircut to still rip my heart to shreds with her impossible jaw. Joan of Arc’s not a male character, obviously, but she still passes herself off as a soldier and gets mistaken for a male at least once in the film (I think) so she stays.
7. Salma Hayek, Frida Kahlo. I have no words. I have no words; they should have sent a poet. I WANT TO KISS YOU WITH THE KISSES OF MY MOUTH.
6. Janet McTeer, Albert Nobbs. She looks like Clive Owen. The world has given us a woman with strong shoulders and glossy chestnut hair who wears immaculate ties and who walks upon the earth with her own two feet and looks like Clive goddamn Owen. Thank whatever wretched god bore you and your kin.
5. Gwyneth Paltrow, Shakespeare in Love. GWYNETH. YES. I AM HERE FOR YOU. I AM HERE FOR YOU IN THAT SAUCY LITTLE GOATEE AND THAT INSOUCIANT BLUE JACKET. I would have made out with you so hard at Homecoming. (An aside: Gwyneth Paltrow is Katherine Moennig’s cousin; they are to my knowledge the only family members on this list.) You have a weird newsletter now but once you were the boy-girl of my dreams, Gwyneth, and I’ll never forget you for that. I’m not mad you won the Oscar for this; look at this audition scene. HOT GIRL HIDDEN IN A BOYSUIT HAVING FEELINGS REAL BAD AT THE CEILING.
4. Cate Blanchett, He’s Not There. I didn’t see this movie. Nobody saw this movie. Everybody just watched Cate Blanchett’s scenes on YouTube and wished desperately we were a cigarette between her nervous, slim fingers. I feel nothing for Bob Dylan, but I would follow Cate Blanchett’s Bob Dylan anywhere.
2. Katharine Hepburn, Sylvia Scarlett. If you have not seen Sylvia Scarlett, might I suggest doing so at your earliest convenience? It’s very exciting that she wore the occasional pantsuit in Cary Grant’s Girlfriend Gets A Job, of course, but you haven’t seen Hepburn in menswear until you’ve seen Hepburn In Menswear. (She kisses girls, and puts her hands in her pockets just so, and Spencer Tracy was a goddamned beard and I will go to my grave saying so).
1. Katharine Moennig, Young Americans. Before there was Shane, there was Jake Pratt. And it was good. Young Americans was a summer replacement for Dawson’s Creek that ran for eight episodes, all of which I carefully taped on VHS, even when my family went on vacation the week “Will Bella Scout Her Mom?” aired. I am reduced here to mere syllables: UUNF. HUUURRNNGH. AAAUUUNGH. GNEHHH.
More than almost anybody else on this list, Jake sells maleness in a wholly believable and unique way. There’s no forced “hey-dude” in her voice and very little put-on swagger in her walk. She wears masculinity as well as she wears that motorcycle jacket in episode seven.
Special Category: Music Video
3. Lady Gaga, whatever her male Italian alter ego is. It’s a little James Deen, a little Joyce Hyser. Definitely solid. Excellent pompadour, good jawline.
2. Beyoncé, If I Were A Boy. It’s not drag, exactly, so much as it is a few props that telegraph maleness, but great God, does she look good in a uniform. Ma’am. Sir. Ma’am. Whatever pronoun you like, as long as you’re still in charge.
1. Ciara, Like A Boy. Dear Ciara, Thank you for making me gay.
Doris Day in Calamity Jane, who is not technically cross-dressing only inasmuch as she is always female-identified and acknowledged as such throughout the movie. That said…look at her. I never thought being sexually attracted to Doris Day was possible, but here we are.
Please enjoy “A Woman’s Touch” from that same movie. Hello. What? Yes. How. How. How. But yes. Hello.
Cissy Meldrum from You Rang, M’Lord? Again, not passing herself off as male — just a jolly lesbian in Edwardian-era England with a fondness for Savile Row menswear. The lesbian answer to Niles Crane.
God bless you all and keep you.
Mallory is an Editor of The Toast.