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Leslie Jones on her badass pirate in Our Flag Means Death: ‘Sign me up, I’ll do this for free!’

‘I’ve always wanted to play a woman like that. A swashbuckling woman on the bad side? I love it!’

Leslie Jones holds a dagger to Rhys Darby’s nose in Our Flag Means Death Photo: Aaron Epstein/HBO Max
Tasha Robinson leads Polygon’s movie coverage. She’s covered film, TV, books, and more for 20 years, including at The A.V. Club, The Dissolve, and The Verge.

The HBO Max pirate comedy Our Flag Means Death starts out slow and accelerates fast. And a key part of its pivot from small-scale What We Do in the Shadows-style humor about inept, self-important sailors to a bigger, broader story arrives when Saturday Night Live veteran Leslie Jones shows up as Spanish Jackie, the undisputed queen of the Republic of Pirates. The story is based on the real-life partnership between Blackbeard (Thor: Ragnarok director Taika Waititi) and “gentleman pirate” Stede Bonnet (Rhys Darby), but the show’s aesthetic leans hard into the larger-than-life pop-culture idea of pirates, complete with grand adventures, grotesque violence, and swashbuckling style.

Jones tells Polygon that this image of pirates was a big part of the appeal in taking the role. “My agent sent it over and said, ‘They’re really interested in having you play this pirate,’” she says. “I was like, ‘Oh, I’m on!’ As soon as they said ‘pirate,’ I was like, ‘Are you kidding me? I get to wear pirate boots? Yes, for sure.’ They told me ‘Spanish Jackie has a wooden hand and like 20 husbands.’ I was like, ‘Sign me up, I’ll do this for free!’”

And sure enough, she did get those pirate boots she signed on for: “I got nice Rick James boots,” she cackles. “The ones that go up to the knee.”

Spanish Jackie, who first shows up in episode 3 and memorably re-emerges as the season’s plotlines coalesce, is a ruthless bar owner with a longstanding grudge against one of Stede’s sailors. Fred Armisen plays Geraldo, her head bartender and one of her many hapless husbands. When a few sailors from the main cast re-enter Jackie’s life and her bar, she gets a grand entrance, complete with her own ominous theme music and a slow, dramatic zoom in to the table where she’s lurking in darkness. Later, Stede is introduced to the jar of severed noses she keeps on the bar, a testament to how many enemies she’s taken down.

Leslie Jones looming over the camera as Spanish Jackie in Our Flag Means Death Photo: Aaron Epstein/HBO Max

“I got to be an all-around badass,” Jones says. “I’ve always wanted to play a girl who is tough as a dude. I got to smoke cigars, to intimidate dudes. People have to be scared of me. I love that. I’ve always wanted to play a woman like that. A swashbuckling woman on the bad side? A thief, who gets to run stuff, and men fear her, and then she’s still charming enough to have 20 husbands? And she gets to look good, too? I love it! I love that she isn’t some dirty pirate woman. She’s like ‘Oh, nah, nah. Y’all can look good? So can I. Where you go and get your velvet? I go and get mines, you know?’”

Jones has been performing stand-up since the 1980s, but she’s also been all over the entertainment field. She’s appeared in movies like Trainwreck and Coming 2 America, and co-starred in Paul Feig’s 2016 take on Ghostbusters. She hosts the ABC game show Supermarket Sweep, and recently released a new Netflix comedy special marking her 50th birthday. In 2014, she became the oldest performer hired to the Saturday Night Live cast, and she stayed with the show for five years. She’s built an entire fandom around her Twitter persona and her live Twitter and Instagram reactions to movies and sports events, including the Olympic Games. But she says it’s still rare for her to get roles like Spanish Jackie, where she’s being asked to play a character instead of a version of herself.

“This pirate thing was different for me because they really was asking me to act,” she says. “I like to do stuff that makes me come out of whatever people expect. So I do look for projects like that.”

For Jackie’s introduction episode, Jones worked with Nacho Vigalondo, director of Timecrimes, the kaiju movie Colossal, and the Blumhouse movie Pooka! “I loved him,” she says. “He was such a good director. The thing I loved about him and [creator and showrunner] David Jenkins is — they came up to me like, ‘We love Leslie Jones, we’re so glad Leslie Jones is here. But we want Spanish Jackie when those cameras come on.’ And I was just like, ‘Yes, I love that!’ Because most times, people are like, ‘Oh, just put some Leslie Jones on it!’ And I’m like, ‘No, I want to play the character. Because that’s what’s gonna broaden my portfolio.’”

Still, Jones says there was room for improv on the set. “You cannot have me and Fred Armisen on a set and not improv. There’s just no not doing that. […] It was so easy to go back and forth with Fred, because he would pick up on what I was doing, I would pick up on what he was doing, it was insane. And then the other actors, I got so many pointers where I was like, ‘Oh, damn, that is — oh, I didn’t know that — OK, that’s how you — wow, this is really good stuff!’”

Part of what she learned on the Our Flag Means Death set, she says, was just about playing action scenes — how to cheat a knife strike at another actor’s face so it looks good for the camera, how to lunge and fall in realistic ways. “The stunt dude that taught us our moves was frickin’ sensational. Steve was off the chain. There was times when I was like, ‘How’s he gonna make this look real?’ And he’d say ‘Just fall this way.’ He would do every move first. He made me look like I could fight.”

But some of the better suggestions she got from Vigalondo were about evoking power with minimal movement and action. “The note I most loved was, ‘You don’t have to lean in so they can hear you. You stay where you are, and they lean into you so you can hear them,’” she says. “‘You don’t have to ask for something — you look at them, and they give it to you, because you’re Spanish Jackie. You won wars. You’ve fought battles. You don’t have to answer to nobody. Commanders are scared of you.’ I was like, ‘Dope.’ He’s telling me this, and my back is getting straighter the whole time. I love it.”

Not that Leslie Jones has any trouble portraying confidence and strength. She’s stood tall and kept her poise through a number of high-profile public battles over the past few years, particularly in the wake of Feig’s Ghostbusters, which turned her into a target for racist and sexist trolls. The harassment campaign that temporarily drove her off Twitter was a bad look for the site, which updated its policies and wound up banning alt-right figure Milo Yiannopoulos for his role in the campaign against her. In retaliation, her attackers hacked her website to dox her and post inflammatory pictures. The online war boosted her profile and drew her widespread support, but has also kept her in the spotlight for exasperating reasons that have nothing to do with her comedy or her career.

Leslie Jones and Fred Armisen in Our Flag Means Death Photo: Aaron Epstein/HBO Max

Asked whether these kinds of public battles have affected her career choices or the roles she takes, though, she just laughs.

“Let me tell you something about me,” Jones tells Polygon. “I’m 54 years old. The battles that I fight in this business ain’t shit compared to what I’ve come from. To make it to where I am, I have fought battles that make those battles look like bitches. […] Nah, I’ve seen things and done things and been places. These new battles don’t so much shape me as inform me of what to do. It doesn’t make me fearful, because I know who I am. I know what I am. I know what I can give.

“And I know I’m not perfect, but I know I’m the shit. You’re not going to tell me better than what the fuck I say in my head. I don’t believe you, I believe me. So people can throw what the fuck they want at me. I love it. I’m a comedian. Do you know how bad I’ve been talked about? When people say stuff about me, I’ll be like, ‘That wasn’t even a good one.’ I want to answer them, like, ‘You know what you could have said that would have been really funny?’”

What does affect her choice of roles, though, is any chance she sees to stretch and surprise people. “I do like to do things they don’t expect me to do. I like to be vulnerable when they don’t expect it. Everybody hears ‘Leslie Jones’ and thinks, ‘Oh, she’s funny.’ Yeah, I’m funny, because I am a comedian. But I also can do dramatic. I want to be a serial-killer character. I want to do everything. I’m not just one base. But you do have to show people first. So that’s how I pick projects. I go, ‘OK, I’ve done Coming 2 America, I’ve done the SNL-type thing. Now let me do something different.’”

There are limits to what she’s willing to do though, even to play a badass, swashbuckling pirate who intimidates and bullies the star of the series. “I don’t know about going on a ship,” she says. “But you know, baby steps.”

And she isn’t angry that she didn’t get a parrot to complete her pirate look. “I don’t want no damn pirate parrot,” she says. “I was like, ‘Can I get, like, a little sidekick or something?’ But no parrot. No. ’Cause I’m one of those people that actually know about birds. Birds are evil.”

Season 1 of Our Flag Means Death is now streaming on HBO Max, with new episodes on Thursdays.