Maybe Happy Ending‘s Stella Cole Shares Her Playlist of Showbiz Classics

Jazz Monthly exclusive, Helperbots: A new crooner is jazzing up the world of Maybe Happy Ending! That’s right, on October 20, Dez Duron handed Gil Brentley’s trusty mic to jazz-pop artist Stella Cole, who’s making history as the first woman to ever play the character.

“Being part of Maybe Happy Ending is beyond a dream come true,” Cole tells Ticketmaster. “I’ve been dreaming of being on Broadway since I knew it existed. As a five-year-old, I was making my family come up to me and ask to sign their programs. So it feels so surreal to be coming out of the stage door to sign people’s playbills.”

Cole’s stint as Gil — whose name is now pronounced “Jill,” for the record — runs through November 15 at the Belasco Theatre. When it came to developing her own, unique take on the jazz-obsessed Oliver’s favorite crooner-turned-chanteuse, the fixture of the New York City jazz scene looked to the leading ladies of Hollywood’s Golden Age.

“I’m so excited to be the first woman playing Gil Brentley,” she says before adding, “Dez seems very inspired by Sinatra, Nat King Cole and Mel Tormé, so it’s been so fun discovering who I want Gil to be.

“Growing up on movies from the ‘50s has been a huge help, because I’m already so familiar with the vocal style and physicality from that era,” the singer continues. “So I’ve been having fun watching old videos of performers like Jane Russell, Marilyn Monroe, Judy Garland and Barbra Streisand to take inspiration.”

Some of those names also appear on the pre-show playlist Cole assembled exclusively for Ticketmaster to help celebrate her Broadway debut.

The 10-track mix features Babs’ famous turn as Fanny Brice in Funny Girl and a double dose of the original Dorothy, which feels especially appropriate considering Cole points out that she’s “channeling a lot of Judy Garland energy into the role.”

Below, check out stories behind all of the songs on Cole’s pre-show playlist for Maybe Happy Ending, including famous movie musical classics by Julie Andrews, Gene Kelly and more.

1. Frank Sinatra – “Theme From New York, New York”

On the day I graduated high school, I drove home listening to this song on repeat! I was dreaming of moving to New York and being on Broadway, and I actually DID IT!! Wow. I have been listening to this on my way to the theater to remind myself I’m truly living the dream.

2. Nat King Cole Trio – “‘Tis Autumn”

I’ve lived in NYC for five years now, but I’m on tour so much that I’ve never been in town to experience autumn in New York! It’s the most magical time of year, and I’ve been loving my daily walks in Central Park. Nat King Cole’s voice helps me romanticize my walk through Times Square, which can be pretty hectic.

3. Judy Garland – “The Trolley Song”

Now we start on the hype songs to get energized before the show. This is from a movie called Meet Me in St. Louis. Manifesting that someone produces this show on Broadway and I get to star in it.

4. Barbra Streisand – “I’m The Greatest Star”

This is the song I ALWAYS play before a show. Singing along with Barbra Streisand as she sings about being the greatest star is exactly the energy I need to step into my Broadway debut. If I’m ever struggling with confidence before a show, it helps to steal a little confidence from Barbra as Fanny Brice.

5. Julie Andrews – “I Have Confidence”

I grew up on The Sound of Music, and this is another great hype song for me. I could lie to seem cool, but this is what I’m actually listening to pre-show. I’m a true musical theater nerd, just listening to my favorite songs from movie musicals.

6. Dick Van Dyke & Julie Andrews – “Jolly Holiday”

I watched Mary Poppins every day when I was a toddler. This song makes me feel so happy and comforted, like a warm blanket!

7. Gene Kelly – “Singin’ In The Rain”

Another comfort song. Watching Gene Kelly dance with that umbrella can turn my whole day around.

8. Judy Garland – “Overture: The Trolley Song/Over the Rainbow/The Man That Got Away (Medley) – Live at Carnegie Hall/1961”

I am channeling a lot of Judy Garland energy into the role of Gil Brentley, so we’ll go double Judy on this playlist. Her concert at Carnegie Hall was such an iconic moment in music history, and you can feel all the energy from the audience during the overture. It gives me so much energy too! When I ran a 10K a few years ago, I had the thought that I was probably the only person listening to the overture of Judy at Carnegie Hall on repeat. [Laughs]

9. Jonathan Groff, New Broadway Cast of Merrily We Roll Along – “Opening Doors”

Merrily We Roll Along is my favorite musical, and has been since I was 18. When I saw the revival with Jonathan Groff, I just cried the entire show. He has been an inspiration since I was in middle school. I love that he leaves absolutely everything he has onstage, and listening to this reminds me to do the same thing.

10. Dez Duron, Will Aronson, Hue Park – “Why Love”

I am the president of Dez Duron’s fan club. He originated the role of Gil Brentley, and I have been listening to him so much in the last month! His voice is RIDICULOUS!! So smooth, so silky, so relaxed — how does he do it? It’s been an honor to step into this role that he created. He’s been such an amazing mentor and friend throughout the last month.

Buy tickets for Maybe Happy Ending via Ticketmaster.