Meet the Cast of Guys & Dolls: Sky Masterson

Our upcoming production of Guys and Dolls is quickly approaching, and our two Sky Masterson’s are excitedly awaiting opening night! These two men have, for the past few months, put their heart and souls into developing their portrayal of the confident, charming gambler! Here’s what they have to say about their experience:

How would you describe Sky Masterson? Matt: “Sky is a confident and independent person who came from very little and has become the best at what he does. The very definition of the self-made man. But for all his swagger, he knows there is something missing. And when it (in the form of Sarah Brown) finally finds him, he finds himself in the unexpected and unusual position of not knowing what to do for probably the first time in his life.”

What is the most difficult part about becoming Sky? Matt: “Matching the bravado that defines him without it appearing hollow or phoney. Sky's confidence is not a facade to cover up insecurity. It's the essence of who he is.” Adam: “When I first started playing Sky I was trying too hard to be cool and suave and controlling. The definition of being suave is to be confident, and to not try hard: Sky may ask Sarah to dinner, but you know that it doesn't matter if she says no - it's all the same to him (or at least he'll have you believe!). The banter with Sarah is also as much about what's not said as it is about the lines. It was difficult, but incredibly rewarding to work with Justine on how to work in that flirtation with those seemingly-innocuous lines, followed by a knowing wink.”

What is the most interesting part about portraying this particular role? Adam: “How truly complex he really is. Sky is not a bad person, but he's no saint either: he's a man of God who can quote scripture, but only because he believes God works on his terms; he's a legend with the NYC gambling crowd, but he was in fact raised from nothing; he coerces Sarah to Havana on a bet, but he nearly ruins his reputation with the gamblers to save her mission from closing. On a more personal note, the scene/song of "My Time of Day" is a favourite moment of mine where we get to see Sky pull back the curtain a bit and explain to Sarah just a little bit of how his world works... and what his real name is (but you'll have to see the show to find that out!).”

How does Sky grow as a person throughout the show? Matt: “Sky learns that he can still be himself but also make room for something more. Sacrificing something, even a big part of your life, is not necessarily the same thing as compromising your true self. And corny as it sounds, love conquers all.”

What is your favourite part of the show? Matt: “I love all the great comic bits of the show- the hilarious scenes with the gamblers, the relationship of Nathan and Adelaide, etc...but I have to admit that selfishly, my favourite part of the show has to be Luck Be a Lady. The chance to sing one of the iconic tunes of the musical theatre repertoire has to be any actor's dream come true.” Adam: “I think it's a tie between "Guys and Dolls" and "If I Were a Bell". "Guys and Dolls" is such a juicy sardonic number: from the very get-go we have this rapid-fire patter of Nicely Nicely Johnson and Benny Southstreet as they almost try to outdo each other with anecdotes about how women have changed the world for "smart businessmen" like themselves. We find it funny because these characters aren't the sharpest tools in the shed and I love how Loesser uses that character trait to turn the meaning of their words against them. As for "If I Were a Bell", this song is genius because you get a huge amount of Sky's character developed by him not singing and being a listener - we finally get to see a moment here where Sky doesn't have a witty retort planned, and by the end he's speechless about what he realizes is happening between him and Sarah. Also, it's probably my favourite melody in the play, so I'm sure that helps.”

What makes this production unique? Matt: “Of course, every production is unique in at least small ways. But in this case, having 2 casts with different actors playing 3 of the 4 leads makes for a fascinating dynamic. Watching Adam's version of Sky has taught me a lot about the character, but saying that, I know it's a Sky that I'm not capable of portraying. We are different people, and our interpretation of the same words is therefore very different. The Sarah's and Adelaide's have a similar process, so we've ended up with what are really 2 completely different versions of this great show. So really, the savvy audience member has only choice- come see the show twice! (at least).” Adam: “Sadly, Guys and Dolls has an entirely undeserved reputation - even in theatre circles - as being trivial, the characters one dimensional, and the songs inserted for hum-value only. Of course, none of these things are true, but I think that it's enduring mega-hit popularity has given rise to a lot of bad productions in the last 60 years that have missed the subtleties of Swerling and Burrows' book, as well as the natural way which Loesser's songs roll off the tongue and this has left audiences with this idea that Guys and Dolls is a fluff musical comedy. Wavestage is different because we didn't start at a place trying to copy the glamourized version of the New York gansters and showgirls, but we began with simple people and how different worlds and classes collided, and then dressed them in the robes of Runyonland. Wavestages' Sky Masterson, Miss Adelaide, or Nicely Nicely Johnson could be just as recognizable in 2014 New York as they are in the 1940's, there's none of this hokey gangsterism that I think a lot of people assume when they see the words "Guys and Dolls". It's just people.”


Don’t miss seeing these gentlemen on stage from November 6-9, 2014 at Newmarket Theatre. Tickets are available online at or by calling the box office at 905-953-5122. Tickets are also available for purchase in person at the box office before the show.