Jacob Dickey doesn’t have a to-do list of musical roles. But if he did have a to-do list, he says, “I feel like Sky Masterson would definitely be on that to-do list.”
Good thing, then, that he’s currently starring as Sky Masterson in the Shakespeare Theatre’s vibrant new production of Guys and Dolls, directed by the Washington National Opera’s Francesca Zambello.
Romping through Runyonland alongside Rob Coletti as fellow gambler Nathan Detroit, Julie Benko as missionary Sarah Brown, and Hayley Podschun as saucy showgirl Miss Adelaide, Dickey cuts a dashing figure in a role he’s practically been preparing for since before his voice changed.
“I saw the movie when I was a kid,” he tells me over a Zoom call a week into the show’s run. “I knew the music, but mainly through the covers from other singers. My husband, for the longest time, is the one who’s been like, ‘You need to play Sky Masterson at some point.’ I’m like, ‘Okay, sure.’ It never comes up, but absolutely. So when this happened, he was just like, ‘Duh.’”
Marlon Brando played the role in the 1955 movie, opposite Frank Sinatra as Nathan Detroit, and the stars’ dapper style made as strong an impression on young Dickey as Frank Loesser’s score. That entire Rat Pack era of smooth crooners and leading men in natty suits imprinted on him.
“I grew up watching Cary Grant and Frank Sinatra and Marlon Brando and all these cool dudes in movies,” Dickey recalls. “I’ve seen it so much that some of the stuff I’m doing in this role, I look back and realize, ‘Oh, that’s because I saw Cary Grant do this at one point in a movie, and now my body’s just doing it because I was so familiar with it.’ Now I’m able to bring it to life onstage with a little bit of my own flavor.”
Bringing his own flavor to a role has been something of a guiding principle for Dickey, who, just under a decade ago, vaulted from a theater degree at Virginia’s James Madison University, to performing on cruise ships, then to Broadway in Disney’s Aladdin following a whirlwind casting camp.
Called in to replace an actor in the show’s ensemble, he wound up going on right away as Aladdin, and stayed with the show for another four years. Since then, Dickey has appeared in the Tony-winning revival of Stephen Sondheim’s Company, and, this year, took center stage alongside Bernadette Peters in the splashy revue Stephen Sondheim’s Old Friends.
Now he’s crooning “Luck Be a Lady” on the Shakespeare’s stage, embodying the legends he grew up on with his own Sky Masterson. “I mean, he’s cool, but I love that he’s pretending to be cool,” Dickey says of the charming gambler.
“My understanding of him is that there is this soft, sweet, romantic underbelly that he hides from a lot of people and that Sarah brings out, which is the best thing to play, because he’s caught off-guard by his own feelings. And I love playing that. I love playing it.”
METRO WEEKLY: So I know you’re a Virginia native and JMU alum, but this is your D.C. theater debut, which is actually surprising to me. What took so long?
JACOB DICKEY: You tell me! I’ve been trying to get into D.C. forever. It just never came to fruition. I think the focus was always New York, New York, New York. And then that ended up being pretty successful for me, which is lovely, but I just have never had a D.C. show come up that worked out the way this one did.
I was thrilled to do it. My husband’s from Norfolk, and so our entire extended family is in Virginia. So being here for this show is special, but also being here for the holidays and seeing my family, which I never get to do, is also doubly special, so it’s a really cool time.
MW: This show is not Shakespeare, but do you think we’d ever see you back here doing Shakespeare?
DICKEY: I would love to do Shakespeare again. I have only ever done one Shakespeare show in my entire life, and that was senior year of college at JMU. I was Romeo in Romeo and Juliet. And you’re like, “Yeah, yeah.”
MW: Well, if you’re going to do Shakespeare, yeah.
DICKEY: It was amazing. I was so nervous going into it. But then there’s a freedom to it. You think Shakespeare’s going to box you in because the language is so specific, but then there’s almost a freedom once you lock into the understanding of what’s going on, and that was really special. I would love to do it again, but I’ve never had the opportunity.
MW: Well, we’ll put that in here and it’s out into the world.
DICKEY: There we go.
MW: Something that you have to play as Sky Masterson that I thought you did well is that we have to believe that love can change this gambler. I know some people who are gamblers, and gamblers gamble. They don’t change easily. What are your thoughts on making that 180-degree turn?
DICKEY: It’s a big musical theater swing, to be honest. You’ve seen the show, the ending, they really just wrap it up, and in a way that I really enjoy. I’m like, “They do not take time.” You have this beautiful buildup, so it’s believable, but that last moment is like, “Oh, he’s changed.” It’s the opposite of Grease, kind of. I’m sorry to anybody who hasn’t seen it. I’m ruining the show. It is what it is. It’s been around for a while.
MW: It’s been around a while.
DICKEY: No, I think that is kind of the overarching story, specifically for Sky and Sarah — love does change you. And it changes Sarah, too. She is able to understand that she has blinders on in life with her sole mission of the Mission. For both of them, this love is completely life-shifting in this moment. And I think that’s something that a lot of people can connect to.
I think in my version — and maybe my director would disagree with this — Sky still has a little bit of fun [after] the show. I don’t think he’s completely like, “I am a Bible Christian.” I think the interesting thing is that there is quite a thread of the Bible throughout it. I do think he has a little bit of faith in him, which is an interesting thing to think about, but I don’t know. I don’t think he’s completely not gambling. I think he’s just honest about it and priorities have shifted, if you will.
MW: I would agree with that assessment. Like I said, I think a betting man is probably always a betting man, even if he’s not betting. Are you a betting man?
DICKEY: No, I really am not. I have no draw to it. I’ve been to Vegas many times, and I’ve been in casinos many times, and I’m great at getting one $20 bill, and when I lose, I lose. I like being around it and like watching people. I have friends who really enjoy it, but I’m not going to be at a table. I don’t want to talk to a real person. I just want to hear sounds, and see colors light up [mimes pulling the lever on a slot machine], and then I get bored. Which is good for me, I think.
MW: I agree with that assessment, too. I have no interest whatsoever in dropping lots of money at a casino. I mean, people bet on everything, just like Sky. Literally, now you can go online and bet on, like, how many times Jonathan Groff is going to spit on the front row. You can bet on anything.
DICKEY: Well, that’s an easy bet. I would actually take that bet, probably. [Laughs.]
MW: Something else Sky gets to do is sing “Luck Be a Lady,” which is arguably the signature song of the show. Do you feel added responsibility or even maybe an honor, in any musical, I guess, when you’ve got the song that you know people want to hear?
DICKEY: Oh, yeah. I mean, it doesn’t make me nervous. It doesn’t add a layer of anxiety, specifically. It just makes me really excited, because also where “Luck Be a Lady” comes in the show, it’s later in the show. So I do think you get this sense that people are like, “Where is ‘Luck Be a Lady?’ It’s got to happen.” Also, the way the song starts, it’s just like a big hit of a chord, and then it’s, [singing] “They call you Lady Luck.” And you can just feel the audience be like, “Ooh.” It’s really cool. It’s a really cool feeling. And I have known that song forever. So to be able to sing that with this beautiful orchestra in this gorgeous theater, I feel lucky. And it’s a sick song. Come on. We added an option up at the end because why not? It’s 2025.
MW: Do you have to put Sinatra out of your head with that song?
DICKEY: I think it’s probably a conglomeration of a bunch of different crooner sounds. I have had to adjust some vowel sounds because the crooners, Bing especially, was always changing vowels when he was singing, and I just love that. But in musical theater, people need to understand what you’re saying. So that was a shift that I had to make. But I’m sure I feel like all of those vocalists are probably in there somewhere. And what’s nice too is, yes, it is a crooner show, but our music director, Jim [Lowe], specifically was like, “I also want a little bit of that classical legit baritone sound.” So I think I try to do a little bit of a hybrid of it because I can and it’s fun to do.
MW: In this production, and I just want to mention it because it’s such a great moment, that song is preceded by a fantastic dance break. You don’t appear in that dance break, but I’m just curious, are you a dancer? How would you rate your dancing onstage in general?
DICKEY: [Laughs.] How would I rate my dancing onstage in general? Listen, I will dance if I need to dance. I always say I definitely have rhythm. I love to dance. I love to dance off-stage. I can learn choreo. But that level of dancing is not my tea. That’s not what I do. I saw those boys, Josh Bergasse choreographed that, and those boys are dancing. It is top-level. Nobody’s doing less than three flips over themselves. Crazy. I watch it every night because I’m just backstage, and we have monitors. I think it’s so exciting. My husband saw it, and he was like, “It’s just thrilling. It’s like you’re just excited by how much stuff is happening onstage.” Yeah, I think that’s probably one of my favorite parts of the show, and especially because I don’t have to do it.
MW: That is a sensational part of the show. Actually, that makes me think, I’ve seen lots of other good dance breaks this season, Fiddler on the Roof, Damn Yankees. Have you seen any other shows here while you’ve been here?
DICKEY: We saw Damn Yankees the first week we were here. I loved Damn Yankees. That was actually also my first time being at Arena Stage. I thought it was amazing. I knew nothing about the show leading up to it except for maybe one song, “Lola.” But I thought it was awesome. I thought the production was so smart and obviously the talent is incredible there.
MW: So what was the first musical you saw that made an impact?
DICKEY: First musical I saw… I grew up with movie musicals, so I think the first two I can think of are West Side Story and Singin’ in the Rain. Those two were kind of on repeat in my house. My mom’s Puerto Rican, so I think that was the draw to West Side Story, and then obviously it’s an amazing musical. But in person, the first show I saw live that I can remember being like, “Oh, this is something,” was Thoroughly Modern Millie on Broadway. That was my first Broadway show when I was in seventh grade. And that was like, “Oh, wait, this is something. This audience…” I just remember laughing, in seventh grade, laughing so hard at it, and everyone else laughing and realizing, “Oh, you can do this live.” Because I’d had so many movie musicals growing up. So I think those are probably the first ones.
MW: The male lead in Thoroughly Modern Millie, what does he get to do?
DICKEY: Oh, he gets like one great song, [singing] “I turned a corner, stopped on a dime.” And then he gets another one in act two when he’s in jail, something like that. I forget. But honestly, it wasn’t even that I saw myself in him. I think I just wanted to be Millie. You know?
MW: That’s what I was trying to get at.
DICKEY: Oh, well, I mean, Millie, she was funny, and she was sexy, and she did dance a lot, which in my version she wouldn’t be dancing as much, but she did dance a lot.
MW: We’re going to get you dancing. I want to see that.
DICKEY: Listen, I mean, I was in Aladdin for so long. There’s a lot of dancing. It’s not that I’m incapable. I just would rather not. [Laughs.]
MW: I know you grew up with a military background. Did you have to come out as a musical theater kid?
DICKEY: I love that. No, my parents are both very musical. They both love music. My dad taught himself the drums. He’s an incredible drummer and guitarist. My mom’s a singer. I was in piano and we were very church-based growing up, and so they were also always involved in the worship team. So music was always a part of my life, and that was my gateway into it. I started singing in church. And then we moved a lot. So we ended up at a church that had a great kids’ theater program that they did.
MW: Lucky you.
DICKEY: I did that, and then I went to a community theater, and then it was high school. So it kind of just developed from there. I was homeschooled until eighth grade, so activities were huge. I mean, they always are for kids, but especially when you’re at home every single day. My mom’s like, “Get out of the house.” So activities were big, and they just loved it when we loved something. So we played sports. I played sports my whole life, but also performing was just kind of part of it.
Then, when I decided to go to college for theater, my dad — and I’m now in my mid-30s, and he was correct — he was like, “Maybe have another thing you can do to make money.” Now I’m at a point where I’m like, “That would’ve been really smart.” But at the time I was like, “No, Dad.” And obviously, it’s worked out, but I think people hear military, homeschool, raised in the church, and they’re like, “How did you survive?” And my parents, they just wanted us to be happy and do something that we were successful at. And I’ve been successful at this, and I’m very happy.
MW: It sounds like good fortune. I’ve read about your debut on Broadway, but I would love to hear it from you. I know that Disney hosted an Aladdin performer camp, which was not necessarily going to lead to those performers, or you in particular, doing Aladdin on Broadway, but that is exactly what it led to. At what point from finishing the workshop to getting to do the show did you learn what you would be doing on Broadway?
DICKEY: Well, I mean, speaking of good fortune, the good fortune for me started before that, because this is how this industry works. It’s like who you end up working with ends up being the next job. And my first professional job from moving to New York was on a cruise ship. I did Mamma Mia on Royal Caribbean. And at the time, Eric Woodall was the resident director for all Mamma Mia productions, a lot of them. And he happened to be the director for that one. He also happened to be the head of casting at Tara Rubin, who cast Aladdin. So I was Sky [in Mamma Mia] and at one point during rehearsals, he asked had I ever been in for Aladdin? I’m like, “No, I can never do that.” Because also Aladdin taps in it. And I remember thinking, “Can’t tap.” I say that in quotes, as I learned [to tap] later. But Eric Woodall got me into those auditions and really pushed me through the rounds, because I was a baby. I knew what I was doing, but I didn’t know what I was doing. And especially for that big of a part, and Disney, they look for specific things. So I had actually gone through a whole audition process the fall before Aladdin camp, for Aladdin. It didn’t go my way, in the sense that I didn’t get Aladdin at the time, but they wanted me to come back for Aladdin camp.
MW: You were on the radar.
DICKEY: Right. And Aladdin camp was like a four-day thing with a bunch of other guys. I think that was in January. And then I got the call for an immediate replacement to be an understudy ensemble player in February. So it was maybe even less than a month later, a guy was leaving to do another show. And they called me and then offered it to me on a Friday. I accepted, and I went in for a fitting the next day, and then was in rehearsals the next week, which is crazy, but an immediate replacement is an immediate replacement. They’re not joking.
MW: I knew that companies, especially a big company like Disney, developed talent. I wasn’t aware these camps were specifically built around a show. Had you done any for any other show?
DICKEY: No. And I actually don’t know if they do them anymore. They did them at the beginning of the run. It had started as a Genie camp because Genie is such a specific role, so demanding, that they had that for a while. And then at some point, I’m not even sure in what number I was, but at some point, they started doing the same thing for Aladdin.
MW: Fast-forward to this year, you were on Broadway doing Stephen Sondheim’s Old Friends with, you know, Bernadette Peters. What songs were you singing with Bernadette Peters, and what was that like?
DICKEY: That was really special. I mean, that goes without saying. My big songs were “Hello, Little Girl,” where I sang the Wolf’s part opposite Bernadette Peters as Little Red. And then I also sang “Sunday,” opposite Bernadette Peters as Dot. I played George.
MW: Wow.
DICKEY: Which is crazy. That was a big group number. So we really just started it out with a little bit of scene work, but I mean, scene work, doing that with Bernadette was the craziest thing I’ve ever done. I sang “Being Alive.” We sang the West Side Story “Tonight” quintet — I was Bernardo. I sang the Judge’s part on “Pretty Women,” which was my fun, little bass moment. And then “Waiting for the Girls Upstairs,” which is a song from Follies, which was a cute trio with boys. I think that’s it. I feel like I’m forgetting one, but I had an amazing track in that. That also, again, good fortune, that’s what this industry is. I had auditioned for that show while I was on tour with Company the year prior, didn’t get a call back, didn’t hear anything. And I was like, “Well, that’s weird. I was kind of perfect for that, whatever.” It happens. It happens.
And then the cast announcement came out, and a week later, they called me and were like, “Hey, somebody dropped. We need you to come in.” I booked it within a month. So I joined the cast, myself and Kyle Selig were two replacements, and we joined the cast less than a month before rehearsal started, so it was extra wild. It was so unexpected. I really had no idea what my track was going to be in it. I just knew that I was singing “Hello, Little Girl” with Bernadette. And my final callback was with Bernadette, was like, “We need to make sure that things are good, she’s comfortable, you’re comfortable, we’re all good.” And they were.
MW: So everybody was comfortable?
DICKEY: Everyone was happy. Yeah, it was amazing. I mean, I’ve had a few chemistry tests in my life, but never once with Bernadette Peters. And she was so sweet. I just remember the whole time she was trying to remember her blocking, because she had done the show before in the West End, and she was trying to remember her blocking. And I just remember being like, “I’m just going to follow you. I have no blocking, so please do whatever you need to do.” But she was doing it from a sweet place of like, “I want it to be right for you. I want to make sure,” because it was being filmed and Cameron Mackintosh was watching it.
But she was so sweet, and she was everything that I was hoping she would be, just generous, and lovely, and funny, and she loved playing Little Red. That little moment with us was one of the only sexy parts in the show, and Bernadette loves to be sexy, so we were both sexy together.
MW: Damn, why isn’t that on YouTube? They need to put that up.
DICKEY: I don’t know. I wish it was on YouTube. It was so fun. I was wearing fake leather pants, and wolf ears, and you know, it was quite a furry experience.
MW: I found a quote of yours from around the time when you first got Aladdin. I’m going to throw a quote at you that you probably haven’t heard for a long, long time.
DICKEY: I love that, I love that. Of course.
MW: You had advice for aspiring actors that started with you pointing out that you think “What sets people apart who are successful is those who come into the room like, ‘This is who I am, this is what I have to offer, and I’m not pretending to be anything else.’ Be yourself and accept how special you are because that’s what will make you succeed.” Which sounds like really good advice. Has that advice changed at all in the eight years since that article appeared in JMU’s newspaper The Breeze?
DICKEY: No, it hasn’t. That was good advice, young Jacob. It hasn’t. That’s still stuff I say to young kids. I would say I was probably giving that advice to myself as well, because I can look back, and being a gay man coming into this industry, and being a gay man with the look I have — which is, to be honest, like a straight leading man. I look like a straight leading man. And I was aware of it from a young age. And so I remember in my early career, probably around this time I was saying this, I was always going into rooms kind of pretending a little bit. Yes, I was offering what I could do, but I remember really thinking, “Okay, they want this character to be straight. So drop your voice, buck up, keep your legs apart.”
And that was also just part of Aladdin. I remember, it was a different time, but a lot of the direction was “Hide any sort of femininity.” Mind you, I look back at that time and I was the deepest-speaking Aladdin they had. But in my head, I’m like, “Well, I’ve got to speak deeper, because they keep giving me notes.” But it did teach me a lot. And I think that was what I was probably getting at, and I feel even stronger today.
It’s like I walk into a room who I am. Yes, I’m going to be aware of what the role is. Yes, I’m going to be aware — is a character straight? Is the character gay? I’m a good actor, so I’m going to dip into whatever that may be, but I’m always going to be myself. And I think that that has not only been helpful in my career, but it’s just been helpful in my life.
So much of what we do in this industry is pretending. I mean, we’re pretending to be other people. So when I walk into the room, I try to be my most authentic self, so people know who I am as a person. It also just makes me feel better because 90 percent of my time is not in an audition room and not onstage, and it’s so much more important to prioritize the life outside of it, which is probably something that I’ve shifted toward in my thirties from my younger self, who was talking about that. It was very career-focused advice, which I appreciate from young Jacob. But now I’m always saying, “Just be happy. Find things outside of theater that bring you joy because theater will bring you joy, but it is not consistent. You’re not always going to be doing this.” And that also ties into, “Just find what you love and who you are as a person and it will reflect in your career.” So I think it’s good advice.
MW: It is.
DICKEY: I don’t know if Jacob was taking it at the time, but it worked out.
MW: You mentioned something about being a gay man playing straight leading man roles, which I’ve actually just been reading about this week as it pertains to people like Jonathan Bailey and Colman Domingo. We have — more these days than in previous eras — actors who are leading men and out, and not like glass closet out, but like everybody knows they’re out. I’m not going to mention a name, but there is a really prominent glass closet out movie star at the moment.
DICKEY: Oh, yes, correct. I know exactly who you’re talking about.
MW: And everybody knows. It’s like he’s the Jodie Foster of our moment. But do you think that the industry has shifted a little bit in that, not just the audiences, but the people who make the hiring decisions are okay with actors who everybody knows are gay playing straight leading roles?
DICKEY: I think it’s shifted. I mean, I think there’s always a way to go. I think we still haven’t seen… Well, the actor we have not named has played a Marvel superhero. For the most part, I think Jonathan Bailey honestly is a big shift in the culture because he’s gay, gay, gay, gay, gay, gay, a gay boy. He’s gay. And his early career was, and still is, obviously, playing straight romantic leads. But he’s such a great example of like, “That’s just who he is.” He just is this incredibly sexy, confident individual. And I think it’s a great example of Hollywood giving it a chance of, “Oh yeah, sexy is sexy. And a good actor is a good actor.” And the level he’s gotten to this year, I think, is going to pave the way for a lot of things because the higher-ups are, sorry, everyone’s close-minded. Everyone, they look at the numbers and they’re like, “Well, there’s never been a gay man out who has been a superhero, who has led a box office hit, so it could never happen.” And then now it does. And they’re like, “Oh, wait a second. Yeah, I’ve always thought that.”
So I think Jonathan Bailey, and Colman Domingo, too. Colman, the work that he’s done, he’s a chameleon. His ability to dip in and out of these roles is crazy. I’ve seen him in things where I didn’t even realize it was him until halfway through the movie.
I think having those incredibly confident, sexy, smart, intelligent, successful gay men leading these powerhouse films is really important. Now, does that translate to theater? I think theater is so interesting and strange when it comes to gay men, because theater is gay. Theater is gay. It’s gay. But so much, in my experience, not naming names, but I do think there is quite — maybe I’ll get in trouble for saying this — there’s this sense of internalized homophobia that comes from the older generation who are creating the works. Because you look at some of these — I’m just saying it — you look at some of these straight boys who are leading shows, and you’re like, “Now, how did you get there, babe? How did you get there? I know quite a few gay men who are hot as fuck, or who are amazing at that role. Maybe it’s not even about sex appeal, but you got it.” And when I’m in those rooms, I can see that there is that yearning, there’s that fantasy of a gay man of like, “Oh, this straight man.” You know?
MW: Yeah.
DICKEY: Amongst all communities, not just theater. And I think it’s interesting when you look at little casting things, and who’s who, and who’s getting noticed. And I think it’s kind of prevalent through theater in a really strange way, considering so much of it is gay, but that’s my own personal thing.
MW: Not just yours. Actually, the last person I interviewed had that exact thing to say about theater, that everybody considers it a really gay or just queer-friendly community, and there are aspects of it that are really still closed-minded about that.
DICKEY: Yeah. I mean, it’s who’s making the decisions at the top, at the end of the day. And if those people are not opening their minds and allowing different perspectives to come in, then it’s going to stay the same.
MW: Well, it’s shifting with some people.
DICKEY: Oh, totally. Totally.
MW: So, now I can just go straight to the last really important question, your one hard-hitting question: Are you watching Heated Rivalry? Have you had time?
DICKEY: [Laughs.] Wow. I can’t believe you’re asking me this now. I haven’t started it. The thing is, here’s the thing, I am going to start it. I just don’t know how it’s going to draw me in, because I’ve heard that while the booties are good and the bodies are good, and the sex is hot, there’s not much else going on. I could be incorrect. I’m glad to be proven wrong, but I haven’t started because I need to be pulled in, in other ways too. But let me tell you what, I’ll be Googling those images.
MW: You said that you’re a sporting guy, maybe it’ll change how you think about hockey.
DICKEY: I’ve never once thought about hockey. That’s not my sport.
MW: Well, here’s to making that change, because you’re going to watch it.
DICKEY: I am going to. It’s inevitable. I’m going to be infected by some bug that’s going to have it on at night. Although I did say to my gay friends here, I’m like, “I don’t know if I can watch this in a group setting because…” Okay.
MW: In certain groups. It’s not for post-Thanksgiving dinner with the family.
DICKEY: Oh, I didn’t even mean it’s going to make me uncomfortable. I meant, I’m going to be ready to go. You know what I mean?
MW: Okay. Well, then find the right group.
DICKEY: There we go. See? I need to find the right group.
Guys and Dolls has been extended through Jan. 8 at Sidney Harman Hall, 610 F St. NW. Tickets start at $43. Call 202-547-1122, or visit shakespearetheatre.org.
Follow Jacob Dickey on Instagram at @js_dickey.
Source: Metro Weekly – www.metroweekly.com
