On Point With: James Oblak

Imagine being a gorgeous and charismatic musician who is also extremely talented, creative and disciplined enough to have released your own original album. Now stop imagining, because you’re clearly James Oblak… and the new season of your Fire Island show premieres this weekend! [Cover Photo: John Kale]


Thotyssey: Hello James! It’s a lovely day in New York City right now; are you on Fire Island yet?

James Oblak: Yes, I’m out here every weekend. Actually, I’m headed back to the city now.

It’s only been a few weeks, but how has the FI season been treating you so far?

It’s nice. This year I’ve been able to get my own place out there for the weekends, and really treat it like a working vacation. Plus, I’m super excited for my show to start at Cherrys’ on the Bay Memorial Day Weekend!

[Photo: Korey Smerk]

I see you’re from Cleveland… were you always performing in some way while growing up there?

Yeah! I grew up in Ohio, just a bit south of Cleveland. I started playing the piano at a very young age, and my first ambitions were to be a singer / songwriter. I then started getting into acting and musical theatre, and pursued that so I could get a degree and perform. The piano performance kind of came full circle when I moved to NYC and needed some performance work while I auditioned for acting gigs.

You’ve done lots of regional and touring productions of big musicals at this point: Mamma Mia, Avenue Q, Legally Blonde, Hairspray… have you had an overall favorite experience on the stage as far as musicals go?

That’s tough–each show holds a special moment in my career and artistic journey. The Legally Blonde national tour was really special; I played Warner, which was a blast. But I also clicked so well the rest of the members on tour. It was a really good company.

Do you have a dream role on the stage?

Shakespeare in Something Rotten is one I am really getting into. Also, a childhood fantasy would be Fiyero in Wicked.

Your work in the piano bar scene here at venues like Uncle Charlie’s, Club Cumming and the Townhouse is always very well-received. What are your specialties on the piano? And… what’s a really annoying song that everyone always wants to hear, lol?

I love doing female pop covers. The crowd goes wild for some throwback Britney or Taylor Swift.
But I’ll also give you your piano classics like Elton John, Billy Joel and Jerry Lee Lewis.

An annoying song–that’s funny! Honestly, if somebody asks for it and I know how to play it, it’s always a win. It’s annoying when they just expect you to know everything, and they’re super insistent that you play a song that you’re not too familiar with. I’m always like, “okay I’ll play it, but you asked for it if it’s not great,” haha!

Recently a promoter posted on Facebook that he was looking for a really good-looking and talented pianist, and, like, 90 people responded with your name!

Aw, that’s sweet. Maybe the looks compensate for those annoying songs I don’t know how to play, lol!

You released a whole self-titled album in 2019.

Yes! I self-produced the album on my own; it’s all my original music, lyrically driven contemporary pop. I’ve heard it described as a mix of Gavin DeGraw, Mika, and Shawn Mendes. I’m really proud of what I did with what little I had to work with, actually. It was just me and a few friends doing it together. I think we spent two days at a studio in Pennsylvania, and just had a really good time doing it. The first day was just a dream, hearing the things in my head come to life.

I see it as an unfinished process, really. Just something to put my points of view, sound, and style out there. These things shift and change, and as you grow as an artist you listen back and think “oh wow, I totally would have done something different there.” So often, artists don’t publish because they think it’s not perfect or they didn’t produce it with enough spectacle. For me. I just wanted it out there, I kept telling myself, “just do it James, just put it out and the rest will follow.” I’m glad I took [that advice] and just did it.

[Photo: John Kale]

It’s an extraordinary achievement! Do you randomly find yourself writing music as inspiration comes, or do you have to sit down and say “okay, it’s time to brainstorm?”

Both. The music always comes to me at random; maybe it’s a melody, or some kind of hook. But then there’s always a moment where I have to tie the ideas together, and sit down and figure out structurally what’s going on. But I never force it.

Does the idea of maybe writing a whole original musical, or at least the songbook, hold any appeal to you?

That seems like a very big undertaking. But most of my songs are story-driven and work in relation to each other, so I don’t think it’s so far off.

Maybe you’ve already started writing one without realizing!

What year did you start bartending and performing at Cherry’s, and what do you most enjoy about being there?

It was a total accident that I started last year. I was supposed to be touring all year, so my apartment in NYC was sublet. So when everything shut down and I was abroad, I was like, “well dang, I don’t want to kick my friend out of the apartment during the pandemic to just not work and pay NYC rent.” So a friend of mine and I actually contacted a few bar owners on Fire Island to see if we could rent out a room in some staff housing that wasn’t being used. We moved out there super early in the season, with the thought that if things got worse we’d be safe quarantining out there. But if things got better, we could do some outdoor shows / work and also be close enough to get to NYC if we needed.

The fact that the show worked and the community really embraced me is my favorite part. Cherry Grove is such a special place, and I was so lucky that they took a chance on me and gave me a platform. People always show up and support, and to have been able to work and perform during that quarantine summer was an extreme blessing.

Cherry’s (and really all the businesses on the Grove) did very well with managing lockdown protocol last year, but there was still some much lambasted foolishness on behalf of the patrons elsewhere on the Island.

There were so many hoops to jump through to keep the place open and safe. It was an incredible feat; it relied on each person to be responsible and represent ourselves in a way that kept the community safe. Huge kudos to the small business owners of Cherry Grove for taking on the challenge and keeping nightlife performers employed.

Yes! And we’re in for a great season this summer. For one thing, your show “James Oblak on the Bay” premieres at Cherry’s this Friday at 6pm! Tell us what’s in store for us.

A lot of fun! I’m so excited to play out there again. I’ve got a lot of new songs to play, and some usual crowd pleasers. I always try to incorporate some recent Top 40, with my own spin. It actually was quite a good year for new music.

Yes! Did you have any favorite songs or albums from this year, by the way?

I adore Harry Styles, Dua Lipa, and Chromatica of course. I actually like some of the new flavors Bieber gave us this year, too. Kylie Minogue’s comeback last year was also much needed.

Good stuff all around! Okay, finally: what is an amazing trivia fact about James Oblak that the whole world should know right now?

Hmm… loves pineapple on pizza. Currently binging Ryan Murphy’s new show Halston. And I’m trying to read more, since I have these long commutes back and forth to the city. So send any recommendations my way!

Will do! Thanks, James!


Check Thotyssey’s calendar for James Oblak’s upcoming appearances, and follow him on Facebook, Instagram and YouTube. Stream or download his music on Amazon, Apple, Spotify and all related platforms.

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