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Artfully curated by Culturadar


March 2, 2018

Jennifer Diamond Returns to the Cabaret Stage with "Third Time’s The Charm"

Performer Jennifer Diamond has been busy for the last couple of years: She starred in the hilarious musical comedy Ruthless, went on an international tour with Kristin Chenoweth, and debuted solo shows in two of New York’s most elite music venues.  This month, the veteran of musicals such as Les Misérables, Evita and Into the Woods, returns to the cabaret stage with a new show called Third Time’s The Charm, which she will be performing at the Green Room 42 on March 11.

Jennifer spoke to Culturadar about her experience traveling with a musical theater legend, her dream roles, and her upcoming gig.


Culturadar: You are making your Green Room 42 premiere with "Third Time's The Charm." What is different about this cabaret show from the ones you performed at Feinstein's/54 Below or Joe's Pub?

Jennifer Diamond: I think each show has been a natural next step and progression from the previous.  It's My First Time: Please Be Gentle was more - "Here I am!" and can I even do a solo show?  Then moving downtown to Joe's Pub, I felt more confident and free to let loose, and I invited some special guests to join the party – all while telling my story. Now, coming to Green Room 42 I have a whole new show that not only continues my story but I am bringing my 54 Below and Joe's Pub experience with me.

CR: You recently finished up a run in Ruthless, a relentlessly hilarious show.  Which do you find harder to perform:  musical comedy or dramatic musicals?  Which do you prefer?

JD: Don't make me choose!  But joining Ruthless! was the first time in a long time I wasn't in a dramatic musical with my face covered in dirt so I really got to have fun! I love love love doing comedic material and when it lands it is the most thrilling feeling. I think dramatic musicals have their own unique set of challenges compared to comedy and I don't view one as harder than the other – just very different.  It also really depends who you are working with. Your cast and creative team can make or break the whole experience.  And equally thrilling to laughter from an audience is that intangible excitement before a big dramatic number like "One Day More."  

CR: You performed and toured with Kristin Chenoweth (!).  What was it like to work with such a legendary performer?  How was the overall experience?

JD: Talk about musical comedy genius! Working with Kristin Chenoweth was a dream come true and watching her every night was like a master class. There was a moment during our concert in Melbourne, Australia, we were singing our duet “Enough is Enough” and we were belting our hearts, we caught each other's eyes and I thought “This is it. This is magic.” Touring and singing with KC were some of the best times I have ever had on a stage and she showed me what it is to be a consummate performer.

CR: What are some of your dream roles?

JD: Oh man, well I have to say first and foremost, Elphaba. It just hasn't happened for me yet and I would love to fulfill that dream. Amneris in Aida is a big one for me - and one that I talk about in my new show is Eva in Evita – I have covered the role but never gone on. Other notable roles I would love to do would be Fantine, Aldonza and surprising to some - Amalia in She Loves Me.

CR: You have worked with director Richard Jay-Alexander several times now. Tell us about him as a director and why you enjoy working with him.  

JD: We have! We have known each other for almost 10 years now and have been working together consistently for the last five or six. He's tough and he's tough on me – but that's why I love working with him. There is no time to waste!  He demands excellence at all times and always brings out the best in my work. And even if we disagree on something, I trust that he sees the bigger picture that I don't see and he would never set me up to fail. And he is frustratingly always right!  Always. 


Catch Jennifer’s show, Third Time’s The Charm, on March 11 at Green Room 42.  For tickets and information, visit:

Posted at 1:10 PM