Ryan James Monroe: What If You Fly?

Back by popular demand, singer and prolific storyteller Ryan James Monroe returns to Chelsea Table + Stage for the third concert of his acclaimed 2025 residency. What If You Fly? is a soaring, soul-stirring evening of music, reflection, and vulnerability—an exploration of the risks we take, the dreams we chase, and the courage it takes to leap.

Known for his cinematic voice, raw emotional honesty, and genre-blurring sound that fuses pop, classical, and rock with theatrical flair, Ryan brings a fresh and deeply personal perspective to the stage. Whether you’re nursing a quiet hope or chasing a dream that scares you, this show will speak directly to the part of you that's wondering, “What if I can?”

Blending original songs, reimagined classics, and deeply personal stories, Ryan invites you into a space where fear meets freedom and hope finds harmony. Whether you’ve been following his residency since the first note or are joining the journey for the first time, this is a night you won’t want to miss.

Whether you're a longtime listener or brand new to his world, come see what happens when fear meets flight.

Ryan James Monroe is a powerhouse singer who commands attention with every note. Known for his rich, soulful voice and raw, emotionally charged performances, he effortlessly blends original songs with reimagined classics, leaving audiences spellbound. A natural-born storyteller, Ryan’s music captures the complexity of the human experience, from heartache to triumph, with an authenticity that resonates long after the last chord fades. Fearless, passionate, and unapologetically unique, Ryan James Monroe is an artist who’s redefining what it means to make music that moves the soul. He has been seen in concerts around the world, most recently at The O’Neill, and other iconic venues such as Carnegie Hall, Joe’s Pub, Chelsea Table + Stage, freeFall Theatre, REX Firenze, and The Duplex. Ryan holds a BFA in Music Theatre from Elon University. You can stream Ryan’s music anywhere you stream and you can keep up with him on Instagram @ryanjamesmonroe.

Tracy Stark (Music Director) is a 16-time MAC Award winner, in the categories of Music Director, Piano Bar Entertainer, and Song of the Year. She is also a Bistro Award winner for Musical Direction, the winner of the Dottie Burman Songwriter of the Year Award, and winner of the Broadway World Award for Musical Direction. Tracy has worked with Lesley Gore, Sarah Dash (LaBelle), Phoebe Snow, Karen Black (Golden Globe Winner), Randy Jones (Village People), Jimmy Osmond, Tovah Feldshuh, Eric Millegan, Tonya Pinkins (Tony Winner), Ann Crumb, Marni Nixon, Barb Jungr, Brenda Braxton (Tony nom), Alice Ripley (Tony Winner) and hundreds of other rock, jazz, and broadway vocalists. She has conducted, played, and sung at all the finest and the sleaziest venues all over the world, including Carnegie Hall and Lincoln Center. She has played/conducted on numerous television shows, including The Today Show. Her songs are included on at least 20 different compilations, and have been winning accolades in songwriting competitions for the past 2 decades. She has 3 CD's of original music, the latest of which is on the MIRANDA MUSIC label, with some amazing special guests, including Lesley Gore, Jane Monheit, Nona Hendryx, Karen Black, Ann Hampton Callaway, Barb Jungr, and other great artists! She keeps overly busy, playing between 75-100 different shows per year. She has worked as MD for the Provincetown Cabaret Festival for numerous years, and the O’Neill Cabaret Conference since 2013.

Music Supervision by Thomas Hodges.

Produced by Lindsay Wormser & Ryan James Monroe.

There is a $25 Food and Beverage minimum per person.

Host or Publisher Chelsea Table + Stage