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SuPer’s Drag Race: Judging Our Heroes’ Cross-Dressing Efforts

Eileen Gonzalez

Contributing Editor

Eileen's primary literary love is comic books, but she’s always on the lookout for her next literary adventure no matter what form it takes. She has a Bachelor's in media studies, a Master's in digital communication, a smattering of published short stories, and a seriously cute dog. Follow her on Bluesky.

Drag is nothing new. Exactly how old it is depends on how you define the term, but it certainly goes back at least as far as the Victorian era, when folks like Boulton and Park in England and William Dorsey Swann in America ran afoul of the law for looking just too fabulous.

Today, in an era when anti-drag and anti-crossdressing laws are once again springing up across America (and, you’ll be happy to know, being shot down as well), I thought it might be nice to remind everyone that even our favorite superheroes have indulged in a bit of drag once in a while — all in the line of duty, but still, drag is drag.

But the real question is: are they any good at it? So today, I’m going to be judging them based on three main criteria:

  1. Plausibility: These disguises are supposed to convince someone that our hero is a woman. Does it work? For how long?
  2. Style: Does our hero manage to capture the style of the era they live in or that they are trying to imitate?
  3. Pizzazz: Anyone can put on a dress, but it takes the right mindset and personality to WEAR a dress. Does our hero have what it takes to commit to the bit?

All of the examples here are of men disguising themselves as women rather than vice versa. Why? Don’t women get to have any cross-dressing fun? Sure! In the real world, they’re called drag kings.

But when superheroines dress as men, it tends not to be as showy (and, let’s face it, played for laughs) as much as when the guys dress as girls. You mostly get things like Supergirl and Lightning Lass dressing as their male counterparts, which allows the artists to just draw “Superman” and “Lightning Lad” looking normal until the big reveal. So while the gals’ disguises are very effective, they don’t give me much to say about them. Unlike these examples…

Captain America in Captain America #2

Captain America, disguised as an old woman, lounges on a bed while smoking a pipe and plotting with Bucky to go to Buckingham Palace.

Plausibility: While everyone seems convinced that Steve is really a grandmother, I have to side-eye his carelessness in these panels. What happens when the maid comes in to clean and smells pipe tobacco? 7/10

Style: For an old woman in the early 1940s, this seems about average. Not “stylish” for sure, but when you want to blend in (especially given that Steve is over six feet!), average is where you want to land. 9/10

Pizzazz: Okay, so Steve is no glamor queen, but I admire his commitment to his own theme. Show him from the waist up and stick a quill pen in his hand, and he looks like he’s one of the Founding Fathers about to sign the Declaration of Independence. 7/10

Overall Score: 7.7/10

Batman in Batman #266

Batman, disguised as a wealthy Southern widow, barges into a hotel and gets a suite.

Plausibility: Batman is truly prepared for any occasion, and that means having this alter-ego of Bertha Carrington-Bridgewater, complete with a seriously detailed backstory, waiting in the wings when Commissioner Gordon needs him to lure out a jewel thief. I totally buy it. 10/10

Style: Alas, we only get to see the coat here, plus all those fancy jewels, so we don’t actually know what he’s wearing. But he put enough effort into the hairdo that I’m willing to give him a decent score. 7/10

Pizzazz: The accent! The attitude! The swagger! Batman has never been so pizzazz-y before or since. 10/10

Overall Score: 9/10

Robin in Batman #626

Tim Drake, dressed as a female medical intern, fends off advances from a male intern and then complains about his disguise to Alfred via a comm link.

Plausibility: Even though it’s the dead of night when there are presumably fewer people around, in the time it took Tim Drake to enter this morgue and get to where he needed to go, he was apparently hit on SEVERAL times. Amazing. 10/10

Style: The scrubs may fit the occasion, but the hair looks a little haphazard. Even in a drawing, it looks like a wig to me. Going by the dialogue, it sounds like Alfred may have been more invested in making sure, ahem, other parts of the disguise were sufficiently convincing. 6/10

Pizzazz: Tim spends the entire time whining about his assignment. He does manage to keep it together around others, but his whole attitude is basically the opposite of pizzazz. Loosen up, Timbo. 2/10

Overall Score: 6/10

Deadpool in Deadpool #4

Deadpool, wearing Marilyn Monroe's iconic white dress and a blonde wig, stabs Zombie President Kennedy while speculating that Jackie was the second shooter.

Plausibility: This is clearly just Deadpool cosplaying as Marilyn Monroe. On the other hand, he does manage to fool Zombie President Kennedy, even after JFK gets a peek up his skirt. 5/10

Style: I assume Deadpool had Monroe’s ensemble from The Seven-Year Itch just stashed in his closet, awaiting the right moment. And it’s impeccable. Look, he even got matching earrings! It’s the details that make or break a disguise. 10/10

Pizzazz: It’s Deadpool. You know he’s got enough pizzazz for both the Marvel AND DC universes. 10/10

Overall score: 8.3/10

Jimmy Olsen in Superman’s Pal, Jimmy Olsen #10

Julian Olsen eagerly dances with "Sue Donym." When her wig falls off, he realizes she is his allegedly dead brother Jimmy.

Plausibility: I docked him a point because his wig falls off very quickly — you’d think he’d know better, given that he’s cross-dressed so much I could do this whole article about him alone — but on the other hand, Jimmy is so convincing as “Sue Donym” that his own brother falls for him, which is, um. An achievement of sorts. 9/10

Style: Jimmy opted for a simple yet very effective and classy ensemble this go-round. The gloves make for an extra glamorous touch. 10/10

Pizzazz: He easily handles every other guy drooling over him at the party but gets flustered when his brother (who also tried to kill him) starts putting the moves on him. Understandable, but I still docked ol’ Jimminy for that. 8/10

Overall Score: 9/10

I can’t believe I’m saying this, but it turns out Batman and Jimmy Olsen have tied as the ultimate superheroic drag queens. Jimmy doesn’t surprise me at all, but Batman? One hopes that there will someday be a comic about these two facing off and trying to outdo each other with their awesome drag skills.