When we first came across Jack Bartholet’s show poster for “ Lady with a Song,” on Instagram, we realized two things—red lipstick and peep-toe heels looks amazing with a business suit and Bartholet is someone we should know.

More than that certain je ne sais quoi, he has an impressive resume as both a tenor singer and artistic director. He has joined voices with Our Lady J, The New York City Gay Men’s Chorus, and appeared in Rocky Mountain Repertory’s production of Almost Heaven: Songs of John Denver. He has also worked as Rufus Wainwright’s assistant.

The next big thing is performing at Pangea’s inaugural Pride festival (June 17-30) on June 27th. If you live in New York or are headed there, get tickets for his show or check out the whole festival.

Several write-ups about you mention that you push boundaries. What should we expect in your latest “Lady with a Song?”

One boundary I push is that I don’t apologize for asking my audience to call me a Lady; A Lady with a Song. In one script draft, I began with an overly wordy preface explaining that by calling myself a Lady I was not attempting to speak for female voices or trans voices. I am a cis-gender gay man and in the speech, I attempted to “get ahead” of potential criticism by explaining that. Fortunately my director convinced me that once people saw me and heard what I have to sing and say, that they’d know “Lady” is simply an affectionate nickname. One that matches some of the silly, femme energy that I bring to the show (and my life) and a title I celebrate. I think the boundary pushing starts there. While I don’t think it’s too, too daring to twirl in a pink petticoat while singing an Ethel Merman song, I also recognize that it’s not necessarily what you might think I’d be doing. I’m not in a suit and tie crooning standards. Without steering my audience into a total sadness, I also bring up some truth that doesn’t exactly provoke a knee slap. 

In one word, what makes a good show?

“Wow!” [the moment you think/feel/say] 

If you had one person, living or dead to share a stage with, who would you choose?

Can I do living and dead?

Let’s say, since it’s nearly World Pride, all hail Judy Garland. Judy would likely be the answer to this question from most gay cabaret singers. Her connection to the LGBTQA community and her icon status are too exciting to name anyone else for me…though her daughter Liza would be equally thrilling. If she agreed to share the stage with me, I’d undoubtedly be upstaged by her monstrous talent and charm, but I’d have shared the stage with one of the world’s greatest entertainers.

Living… I would say my former boss, now friend Rufus Wainwright. I was his assistant for a while a few years ago. I was quickly thrust into the role knowing and respecting who he was and I wanted to do a good job. While I focused on the tasks at hand, I sometimes forgot to stand back and see what an incredible artist Rufus is. The first concert I attended no longer as his assistant was here in New York. I sat in the audience and soaked it all in: what an insanely beautiful, passionate, and unique performer.

He’s done some amazing collaborations and has shared the stage with gads of stars I admire. His voice is so, so powerful. We’re both tenors and share similar sensibilities so I think we’d have fun. 

You seem to promote your events very well… what is your best piece of advice to performers on how to promote their events?

I did a run in January and an encore show in March for a total of four shows. I have only posted four or five times on Instagram and have done a handful of stories. I don’t think you should over do it when it comes to posting promotional stuff. People want to you to be real on social media. I don’t want what I post to be exclusively “Lady with a Song.” I also want to post things that make me laugh, smile and think.

I do my best promotion in person. If I’m invited to an event, I go and I promote my show once I’ve connected to someone. I think it’s good not to be so ultra-branded. You have to believe in your show. Once they do, hopefully you’ll get repeat audiences and word of mouth will spread. (If you’re reading this, why don’t you buy a ticket now?)

You’re performing Lady with a Song at Pangea. What part of performing there excites you the most?

I’m part of their first annual Pride Festival because after my first run of the show back in January, the owners approached me about participating. That’s to say, the two gentlemen who run Pangea [Stephen and Arnaldo] and the whole staff for that matter, are excited about what you’re doing. That makes you feel very supported. They incubate projects and make artistic connections. When I was dreaming up my venue for Lady with a Song, one of the most important things to me was atmosphere. The first show I saw there, [Penny Arcade] I remember thinking how great it was walk to the back of a restaurant to a small stage, to see art on the walls, real candles burning as opposed to fake ones and a thoughtful food and drink menu. Pangea has a cool factor and I like knowing I’m performing in the same room as other artists I respect (Lady Rizo, John Cameron Mitchell, Tammy Faye Starlite).

You participated in a residency at the Orchard Project. What should every artist know before their first residency? 

That’s a great question! I certainly had no idea what to expect myself. After inviting one of my friends, now director Julian Fleisher, to a show I did at The Duplex several years ago I received an invitation to come to The Orchard Project to “cook up a new show.” I had highs and lows in that short, ten-day period. For me, cooking up a new show meant a lot of daydreaming. Listening to and researching new music, getting recommendations, imagining how songs would play out in my mind, talking through these ideas. I beat myself up a little because of all this time spent daydreaming when I looked around and saw other artists cranking out tons of work with their collaborators. Ultimately, I got a lot of ideas out and that was really good.

I’d encourage other people to take whatever space they need to dream up their artistic project and not compare yourself to the other artists around you. There is basically nothing more unhelpful, though it’s very easy to do. I also think you need to ease up on deadlines. While they’re very important, you can’t rush the process. I sat on ideas from my first residency for a year and was lucky enough to return to continue working in a deeper way. Whatever the amount of time that passes in between your ideas and the mounting of your project isn’t worth beating yourself up over. It’s easy to doubt your process and get scared. But it’s up to you to turn that fear around and make big, bold, brave choices. It’s then you’ll discover the joyous moments in your process and you can start to edit. 

You’ve also worked in artist management and festival direction. Do you see yourself returning to those roles?

I always want to work creatively. I love watching artists gain support and making a vision come to life. I started performing when I was twelve and have continued to work in creative spaces my whole life. Working alongside artist managers taught me so much and I do find satisfaction helping to make an artist or a project feel supported enough to share their talents and dazzle the world. Ideally, I’ll be performing a lot more myself…and maybe I’ll need management ;-).

I do have a mind for making things tighter and a number of insanely talented friends, so I wouldn’t be surprised if I used the producer part of my brain more and more. I also have some ideas for a theatre company, Rocky Mountain Repertory Theatre that I’ve worked with over the last ten years and I’d love to see them come true.

How do you manage the stress that often accompanies life as a working artist? 

Well, sometimes I don’t. When I have gigs to perform on the calendar, I’m a pretty happy camper and when I don’t, I find myself in a common valley wondering if I should ever perform again. If that sounds dramatic, it’s because it is! But, I do meditate and journal. I am extraordinarily lucky to have a supportive husband who believes I should continue to create while freelancing. Friends and family who believe in me keep me positive. I try not to put myself down and sometimes I close my eyes and remember watching people connect with and appreciate my work and that fuels me to want to create more.

I also take comfort in the fact that a lot of people I look up to have the same stress and forge ahead. 

Photo credit: Ruthie Darling