Casey Wilson’s Ambitions Goes Full Trump for ‘Black Monday’

I don’t think I can accurately describe Casey Wilson’s Tiffany Georgina–she’s just someone you have to experience. In true ’80s fashion, Tiff was the heir to a vast denim fortune, but she is going through an identity crisis in Season 2 of Showtime’s underrated Wall Street comedy Black Monday. The series has always walked a line between drama and comedy, but Wilson always takes us into blissful absurdity.

Tiff and Andrew Rannells’s Blair set their sights on Washington, D.C. at the beginning of this new season. Now that Blair has officially come out to Tiff, their relationship lingers in a blurry area. Blair starts a dalliance with a closeted congressman, and Tiff is left somewhat adrift. Blair assures her that they have the modern marriage, but can Tiff truly be happy with a man who doesn’t give her the love that she thought she wanted from him? It’s a sad element to drop into the manic chemistry that Wilson and Rannells brilliantly create in their scenes together.

The entire cast is Emmy nomination worthy, but Wilson has yet to be nominated for any television project. She has a natural ability to elevate every scene she’s in—Tiff is bratty, selfish, and her dreams are grandiose and wide. Remember…behind every good man is a woman…with denim goggles on.

Awards Daily: I do think Black Monday is the most underrated comedy on television.

Casey Wilson: I agree, if I may say!

AD: Please do. How close is Tiffany to Tiffany Trump?

CW: (Laughs) I think quite close. She’s really modeled after an amalgamation of snooty, rich bitches, you know? She might be closer to the mother. I’m forgetting her name.

AD: Oh, yeah!

CW: Ivana Trump. She’s closer to Ivana, I think.

AD: Something that is even more fleshed out in this second season so far is the relationship between Tiffany and Blair. They are so ambitious, but there is something very sad about your character because she has to live with this guy that she had feelings for.

CW: Yeah.

AD: You say to him, “Just because we are fake married doesn’t mean we can’t be real friends.” Does she miss him being more? Is she settling?

CW: I think it’s also a relationship that’s very specific to the time. It’s really evolved. I wouldn’t say it’s full blown abusive, but I thought, in the first season, that he was in love with me in this heterosexual relationship. I was just mean and materialistic and wanting to get ahead, but then he came out of the closet and the relationship took a turn. When he did that he became empowered and he’s on his journey. I do think Tiff does miss their relationship more than he does. I think. I don’t think Tiff is drowning in friends and friendship and connection.

AD: Yeah.

CW: She and Blair had something but she also wants to get ahead and they made the dip into politics; it was a brilliant move for Tiff. She loves that mood, and she got that Princess Diana/Nancy Reagan coif.

AD: The helmet hair.

CW: Yes! But I think there’s a little sadness surrounding Blair. Now he is the kind of powerful man she wanted him to be, but he was hiding this secret from her. With him coming into his own, he’s come out of the closet between the two of them, even if he’s not out in his career.

AD: And it has to be harder because it was originally just a secret from her and now it’s something that she has to help him hide.

CW: It’s another layer, yeah. Trying to get back at her parents who kidnapped her.

AD: Of course.

CW: Never forget that she was kidnapped.

AD: Never forget. I couldn’t if I tried.

CW: At the end of last season, of course, they did a beautiful couple dance to “ The Star Bangled Banner,” but it was a sad moment when they were clinking glasses at this understanding that it was over. I do think Blair loves Tiff, too.

AD: Yeah, I don’t think it’s one-sided. He says something about making their marriage their own and playing by their own rules. Even if the love between them isn’t romantic or physical, there’s clearly affection.

CW: I agree. In the way that Blair can, because he’s going to take some sociopathic turns. (Laughs)

AD: I already thought he was becoming a Trump anyway.

CW: Yes. What’s the character that Christian Bale played in American Psycho?

AD: That’s exactly who I thought he was by the end of Season 1! That’s so funny that you say that. He’s Patrick Bateman.

CW: Yes! That’s where we’re headed! He’s so perfect because Blair is so clean-cut.

AD: So you just have to make sure that he doesn’t start chasing you around with a chainsaw.

CW: I mean, I am worried about that happening so…

AD: (Laughs) There’s a very brief moment at the top of the season where Tiff is kicking another man out of bed after Blair and Roger are almost caught in bed together. And that took me by surprise.

CW: What took you by surprise? When you saw the man’s penis?

AD: Yes, I will be honest. (Laughs) Black Monday does give us everything we need.

CW: I love it to be honest. They don’t do female nudity, but they are very fine with male nudity.

AD: Yes, I demand more of it.

CW: Me, too!

AD: Does she not want Blair to see her with another man?

CW: I think she’s too concerned with it getting out. She’s so all about appearances and she doesn’t want to blow their cover. It will be deeply embarrassing if it comes out that her husband is gay. Tiff is still…quite selfish. (Laughs)

AD: You don’t say.

CW: That never changes.

AD: Going with her selfishness is her ruthlessness that comes out a bit more, especially when she kicks her parents out of their house. Is that only enhanced by Blair or is that deep ingrained in her?

CW: I think it’s ingrained in her from her parents owning this empire and how she’s grown up with everything. Those things are really hard to unwind. Blair joining her in this thirst for power has elevated her. And she’s down, you know? She has that lowest point where not even a homeless person will wear her clothes. Tiff is a fighter and she’s gonna end up on top. In Blair, she finds a partner and it’s thrilling.

AD: There are a lot of moments that made me laugh out loud. One of them was the homeless woman giving you back the jacket.

CW: It’s hilarious.

AD: And I think your first line of the season is, “Ironic that Nancy is partying with a bunch of Washington aides after she spent to much time ignoring AIDS.”

CW: (Laughs)

AD: That…absolutely murdered me.

CW: My husband [David Caspe] and Jordan Cahan were like, “. . . can we say that? You know we can!” And that’s what I want people to know about the show is that it’s a hard, funny comedy that also has some romance between Don Cheadle and Regina Hall and some mystery. But it’s a comedy first. It’s a hard comedy that is a commentary on the times. Most of the time when people say “It’s a commentary” you’re like “Oh gooood” because that’s how I feel sometimes. But it’s a comedy in the style of like 30 Rock, if I may be so bold.

AD: And you get to do a lot more absurd things than most of the other characters.

CW: I do, yeah. When I watched back Season 1, Andrew [Rannells] and I were wondering if we were in the same show. (Laughs)

AD: How much freedom do you have? Do you improv?

CW: Andrew and I do, but mainly in small moments. The scripts are so good to start with, but I’ve never met broad comedy that I didn’t like. I love to do other stuff, too, but it’s great being married to a creator because sometimes people don’t see other things you can do. I think it’s a more mature role than I’ve ever played before—I’m not just playing the thirsty friend. I feel like him and Jordan gave me this gift to be out there and fun. But on the other side of things, Regina is holding everything down in, what I hope, is an award-nominated performance! It’s hilarity mixed with being grounded. She’s doing the heavy lifting over there and I come in and get to have fun with Andrew.

AD: I really want more scenes with the two of you together.

CW: I do, too! Regina is my favorite actress working right now. I selfishly want more scenes with her. Coming up I do get to have a lot of scenes with June Diane Raphael where we host a QVC show together and it’s wild what we are selling. We’re selling these modest pants for religious women, so it looks like they’re wearing a skirt but they’re really pants.

AD: That will tap into my childhood because I would watch a lot of QVC for some inexplicable reason.

CW: It’s hypnotic!

AD: Most kids were watching cartoons and I was watching women hocking tacky rings.

CW: I’ll still turn it on to get those dulcet tones. I sometimes enjoy programming that completely ignores what’s going on in the outside world.

AD Especially now. Just take my credit card and buy all the things I don’t need. I just watched Daddio.

CW: Thank you so much for watching that!

AD: It made me laugh out loud and then ripped my heart. Talk to me about it?

CW: My friends and I were planning it as a feature but getting financing together is really Herculean to make stories like that. Where I’m at in my career, it just felt like less pressure to do it as a short. Because it’s been about 12 years after my mom passed and my dad got a perm, I can look back on it and laugh. There’s enough distance. I wanted to tell that story about what grief is like the year after someone passes, when society wants you to move on, but you’re still a mess. You’re still going through the motions, but really everyone is still worried about you.

AD: Yeah.

CW: And it was helpful to have June and Adam there—my best pals—and Michael McKean was so generous and channeled my father in a way that was scary.

AD: I love that you included the pictures in the credits because some people might think, “What father would actually get a perm?” and you were just like this father would get a perm!

CW: My father! I mean it really writes itself. I even left out an arrest, so I was being judicious.

AD: I mean, I smell a sequel. This could be an entire cinematic universe.

CW: We’ve got a lot more.

AD: There is a line in Black Monday where you allude to Trump and all his failures—as if it’s something that Tiff would consider. You mention Tiff: The Game, and I want to know what that would look like.

CW: I think it’d be like Monopoly with winner takes all and you get to behave as horribly as possible. But it’s also fashion and fun.

Black Monday is available to watch on Showtime.