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So there was a giant tumblr meme going around where you genderswap cast shows/movies/what have you. Which is, by the way, both fun and way harder than it looks. I say this because I hadn't seen anyone do a Community genderswap (though I did, in the process of making this, get linked to two, oops), so I decided to take it on.
A week and a half later, it's done, and it was hard. My massive, massive heartfelt thank you goes to
falulatonks, who gave me a million ideas, put up with my whining, and was pretty much the best ever.

Jeff Winger (Joel McHale) → Jen Winger (Colbie Smulders)
Colbie Smulders is someone who gets used a lot in gender-swap casting because she's just so under-appreciated but good. She'd be perfect for Jeff because Robin Scherbatsky is so much like Jeff (that would really be a good cracky crossover pairing, actually), they're both lovable misanthropes who pretend they're just so above everything but really, really care. Plus Colbie Smulders doing deadpan sarcasm is, like, my favorite thing ever next to her being a teenaged pop sensation.

Britta Perry (Gillian Jacobs) → Brian Perry (Chris Pine)
In this casting, we're just going to pretend that we have unlimited funds to make this happen. I know you're all like dubs tee eff Chris Pine? Action hero dude? But yes. Chris Pine would make a magnificent douchey pretentious hipster because he is a douchey pretentious hipster. He does beaten down but with a spark very, very well, which is exactly what the Britta character needs to be hilariously un-hilarious.

Troy Barnes (Donald Glover) → Tricia Barnes (Mindy Kaling)
Oh god, this was by far the MOST IMPOSSIBLE CASTING EVER. First, the problem was I was extremely attached to keeping girl!Troy black because it's such a very different role for a black woman that we hardly ever see - this sort of adorable idiot savant who's hilarious and lovable because of the dimness, but you never feel like you're picking on them or making them the butt of the joke. Actually, it's weird to have a POC female who has a personality that isn't sassy snapping in Z formation (and isn't Zoe from Firefly, who I love forever). The problem is that Hollywood is... a really racist place. It was hard to think of any young black actresses, and thinking of a young black comedic actress is impossible. Except for maybe Raven. Which... no. But even when I said okay, I will literally take any actress, it was still really hard, because in addition to being racist, surprise! Hollywood is also sexist.
But even if it wasn't, the fact of the matter is that Donald Glover is so unique. He's nearly irreplaceable. Mindy Kaling is the only person I would ever entrust the female!Troy to because she has that stupid, but not really stupid, just differently smart, you want to be their best friend vibe. Plus, she can rap. Ding ding!

Annie Edison (Alison Brie) → Andy Edison (Andrew Garfield)
Again, we're pretending I have all the money and influence in the world to make this happen, because how amazing would this be? This role is so perfect for Andrew. He could totally pull off the neurotic over-achiever thing (he could always study Jesse, y'all), plus a lot of what's so inherent to the Annie character is that underlying kittenish and vulnerable sexuality, and you need to sympathize with Annie even when she's neurotic and controlling, you need to make her that everyperson, and that's Andrew's wheelhouse.

Abed Nadir (Danny Pudi) → Abra Nadir (Natalie Morales)
Defense time! I was super-devoted to keeping the minorities minorities, but again, Hollywood sucks, etc etc. Plus, in my defense, Danny Pudi is really half-Indian, not half-Middle Eastern/Arabic/Muslim. So yeah, Natalie Morales is what is referred to in the business as "racially ambiguous", which means basically you don't look at her and know what she is right away and would buy it if she said all sorts of things. So there. Let's pretend my inadvertent racism is justified by decades of racism!
But the real reason I chose Natalie Morales is she's an excellent straightwoman. She's good at being adorable without being vulnerable. She can play the butt of the joke or wide-eyed observer, and you don't feel sorry for her because she's got this core sort of strength. You more feel like, yeah, that chick is cool. I'm with her. You go, Natalie Morales! Which I think, when you have a character who's as disconnected from normalcy as Abed, you need so it doesn't become a pity party. Also, she is tragically under-used in showbiz. And I love her. A lot.

Shirley Bennett (Yvette Nicole Brown) → Sheldon Bennett (Dulé Hill)
My reasoning for this one is simple. One: Gus on Psych pretty much is male!Shirley, and two: Dulé Hill is magnificent and needs to be in everything ever.
No other explanation required.

Pierce Hawthorne (Chevy Chase) → Peggy Hawthorne (Jessica Walter)
Originally, I wanted to cast Jan Hooks as she-Pierce after I saw her play Verna on 30 Rock, but when I went to search for pictures, I couldn't find any, and that's when I remembered Tina Fey saying in a commentary track that she's retired and they were super-lucky to get her at all, so that's out. I was initially eh on casting Jessica Walter because even though she's great at playing the boozy grand dame, the Pierce character is supposed to be a lot less falsely classy. The thing I realized, though, is that while I was semi-rightly picturing her as Lucille Bluth (because she's kind of the female version of Pierce) when she'd probably play the part differently because, you know, she's an actress and that's her job. And she really is a great, great actress who I love and who deserves better than... what bullshit is she on now? 90210?
Though no offense to Jessica Walter (because she's magnificent), but I'd still choose Jan Hooks over her.

Señor Ben Chang (Ken Jeong) → Señora Bonnie Chang (Margaret Cho)
Had to do it. Just had to. They even look related. And I don't mean that in a racist all-Asians-look-alike thing, because Ken Jeong doesn't look like, say John Cho or Grace Park, I mean that in a seriously, they look like siblings, can we please get on that, casting department of Community.

Dean Craig Pelton (Jim Rash) → Dean Cindy Pelton (Jane Lynch)
This is simply gratuitous, because it would be nothing short of emotionally magnificent.
Also, I decided not to go into recurring guest characters, because then I'd have to deal with the reality of a female Starburns, but Ian Duncan (John Oliver's character)? Would be played by Miranda Hart. Such fun!
A week and a half later, it's done, and it was hard. My massive, massive heartfelt thank you goes to
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Jeff Winger (Joel McHale) → Jen Winger (Colbie Smulders)
"What is it about me that makes broken people flock to me? Is it my height? Do huddled masses mistake me for the statue of liberty?"
Colbie Smulders is someone who gets used a lot in gender-swap casting because she's just so under-appreciated but good. She'd be perfect for Jeff because Robin Scherbatsky is so much like Jeff (that would really be a good cracky crossover pairing, actually), they're both lovable misanthropes who pretend they're just so above everything but really, really care. Plus Colbie Smulders doing deadpan sarcasm is, like, my favorite thing ever next to her being a teenaged pop sensation.

Britta Perry (Gillian Jacobs) → Brian Perry (Chris Pine)
"I'm not that cool. I'm not Juno, homeslice."
In this casting, we're just going to pretend that we have unlimited funds to make this happen. I know you're all like dubs tee eff Chris Pine? Action hero dude? But yes. Chris Pine would make a magnificent douchey pretentious hipster because he is a douchey pretentious hipster. He does beaten down but with a spark very, very well, which is exactly what the Britta character needs to be hilariously un-hilarious.

Troy Barnes (Donald Glover) → Tricia Barnes (Mindy Kaling)
Tricia: That's one of my biggest fears.
Abra: What is?
Tricia: If I ever, like, woke up as a donut...
Abra: You would eat yourself?
Tricia: I wouldn't even question it.
Oh god, this was by far the MOST IMPOSSIBLE CASTING EVER. First, the problem was I was extremely attached to keeping girl!Troy black because it's such a very different role for a black woman that we hardly ever see - this sort of adorable idiot savant who's hilarious and lovable because of the dimness, but you never feel like you're picking on them or making them the butt of the joke. Actually, it's weird to have a POC female who has a personality that isn't sassy snapping in Z formation (and isn't Zoe from Firefly, who I love forever). The problem is that Hollywood is... a really racist place. It was hard to think of any young black actresses, and thinking of a young black comedic actress is impossible. Except for maybe Raven. Which... no. But even when I said okay, I will literally take any actress, it was still really hard, because in addition to being racist, surprise! Hollywood is also sexist.
But even if it wasn't, the fact of the matter is that Donald Glover is so unique. He's nearly irreplaceable. Mindy Kaling is the only person I would ever entrust the female!Troy to because she has that stupid, but not really stupid, just differently smart, you want to be their best friend vibe. Plus, she can rap. Ding ding!

Annie Edison (Alison Brie) → Andy Edison (Andrew Garfield)
"I'm not hiding my own pen, you paranoid weirdo! Everybody stay within each other's eyelines please. One of you is a monster."
Again, we're pretending I have all the money and influence in the world to make this happen, because how amazing would this be? This role is so perfect for Andrew. He could totally pull off the neurotic over-achiever thing (he could always study Jesse, y'all), plus a lot of what's so inherent to the Annie character is that underlying kittenish and vulnerable sexuality, and you need to sympathize with Annie even when she's neurotic and controlling, you need to make her that everyperson, and that's Andrew's wheelhouse.

Abed Nadir (Danny Pudi) → Abra Nadir (Natalie Morales)
"I've got self-esteem falling out of my butt. That's why I was willing to change for you guys. When you really know who you are and what you like about yourself, changing for other people isn't such a big deal."
Defense time! I was super-devoted to keeping the minorities minorities, but again, Hollywood sucks, etc etc. Plus, in my defense, Danny Pudi is really half-Indian, not half-Middle Eastern/Arabic/Muslim. So yeah, Natalie Morales is what is referred to in the business as "racially ambiguous", which means basically you don't look at her and know what she is right away and would buy it if she said all sorts of things. So there. Let's pretend my inadvertent racism is justified by decades of racism!
But the real reason I chose Natalie Morales is she's an excellent straightwoman. She's good at being adorable without being vulnerable. She can play the butt of the joke or wide-eyed observer, and you don't feel sorry for her because she's got this core sort of strength. You more feel like, yeah, that chick is cool. I'm with her. You go, Natalie Morales! Which I think, when you have a character who's as disconnected from normalcy as Abed, you need so it doesn't become a pity party. Also, she is tragically under-used in showbiz. And I love her. A lot.

Shirley Bennett (Yvette Nicole Brown) → Sheldon Bennett (Dulé Hill)
"I wasted fifteen years of my life with a woman who left me with nothing but stretch marks and a faulty memory of two great orgasms, and now it's time to get what's mine."
My reasoning for this one is simple. One: Gus on Psych pretty much is male!Shirley, and two: Dulé Hill is magnificent and needs to be in everything ever.
No other explanation required.

Pierce Hawthorne (Chevy Chase) → Peggy Hawthorne (Jessica Walter)
"You all thought I was dead, didn't you?"
Originally, I wanted to cast Jan Hooks as she-Pierce after I saw her play Verna on 30 Rock, but when I went to search for pictures, I couldn't find any, and that's when I remembered Tina Fey saying in a commentary track that she's retired and they were super-lucky to get her at all, so that's out. I was initially eh on casting Jessica Walter because even though she's great at playing the boozy grand dame, the Pierce character is supposed to be a lot less falsely classy. The thing I realized, though, is that while I was semi-rightly picturing her as Lucille Bluth (because she's kind of the female version of Pierce) when she'd probably play the part differently because, you know, she's an actress and that's her job. And she really is a great, great actress who I love and who deserves better than... what bullshit is she on now? 90210?
Though no offense to Jessica Walter (because she's magnificent), but I'd still choose Jan Hooks over her.

Señor Ben Chang (Ken Jeong) → Señora Bonnie Chang (Margaret Cho)
"Guys, I got a confession to make. I took anthropology because I want to be a part of your study group. Now, I gotta do the honest thing and just ask. Is there any room in this pocket for a little spare Chang?"
Had to do it. Just had to. They even look related. And I don't mean that in a racist all-Asians-look-alike thing, because Ken Jeong doesn't look like, say John Cho or Grace Park, I mean that in a seriously, they look like siblings, can we please get on that, casting department of Community.

Dean Craig Pelton (Jim Rash) → Dean Cindy Pelton (Jane Lynch)
"Well, that answers my question. Jen Winger is sexy even in a coffin."
This is simply gratuitous, because it would be nothing short of emotionally magnificent.
Also, I decided not to go into recurring guest characters, because then I'd have to deal with the reality of a female Starburns, but Ian Duncan (John Oliver's character)? Would be played by Miranda Hart. Such fun!