Present Laughter's Holley Fain on Making it to Broadway (with a Gossip Girl Detour)

Age: 28

Hometown: Leawood, Kansas

Currently: Making her Broadway debut as adorably clueless ingenue Daphne Stillington amidst a bevy of heavyweights (including Victor Garber) in Roundabout Theatre Company’s revival of Present Laughter.

Summer Lovin’: Despite a bubbly offstage persona, Fain explains she was “painfully shy” growing up and didn’t break out of her shell until a seventh grade production of Anne of Green Gables. “I don’t know why, but I auditioned—and got the part of Anne," she says. "It was a terrifying and exhilarating experience, which sums up how I still feel about acting today." Soon Fain spent two summers at the esteemed Interlochen Arts Camp in Michigan, where she “fell in love” with acting: “Being in a conservatory in the middle of the woods surrounded by other kids who shared my enthusiasm changed everything. I learned that this is what I would do with the rest of my life. And I learned I wanted to do plays specifically—I could sing, but not like those musical theater kids could. So plays it was!”

Lullaby of (off)Broadway: After earning a BFA in acting at the University of Illinois, Fain did what many would-be actors have done before: “I went right from the cornfields of Illinois to New York City with no connections, no money and the blind optimism it would just work out!” She sent out out hundreds of headshots, “praying for two-scene, non-Equity Shakespeare roles.” Her big break came when Tony-winning director Robert Falls (Death of a Salesman) cast her in Richard Nelson’s Frank Lloyd Wright-inspired dramedy Frank’s Home at Playwrights Horizons. “Did I ever luck out!” she says of the experience. “I was cutting my teeth with seasoned professionals, and the entire cast and team guided me generously. I’d do anything to work with any of them again.”

Boston Bound: Next, Fain found herself at Boston’s Huntington Theatre Company playing Daphne Stillington, a clueless ingenue ("She just can't take a hint!") hung up on disinterested Garry Essendine, an aging stage idol having a midlife crisis. The play? Noel Coward’s comedy Present Laughter. The aging idol? Four-time Tony Award nominee Victor Garber. “I’ll never forget walking into the rehearsal room and Victor Garber greeting me with the warmest smile ever. The show has felt like home ever since.” As the well-reviewed production (also starring Broadway alums Brooks Ashmanskas and Lisa Banes) wound to a close, murmurings of a Broadway transfer began. “I thought, ‘I’ll believe it when I see it,’” Fain recalls. “Then, after Victor’s TV show Eli Stone was cancelled, I ran into him at a restaurant. He jumped up and hugged me and said, ‘It’s happening—we’re going to Broadway!’”

Broadway Gossip: As Present Laughter waited to transfer, Fain took a TV detour, appearing on shows like Lipstick Jungle and Law and Order while still managing to keep her stage roots close. Take, for example, her arc on the hit CW series Gossip Girl, where she guest stars as Maureen, wife of fellow Broadway player Aaron Tveit as Congressman Tripp van der Bilt. “I’d seen Aaron in Next to Normal and we have mutual theater friends, so were comfortable on set from day one. It’s nice going to work knowing your ‘husband’ is a great guy!” While both Tveit and Fain are sweethearts off-screen, their characters are anything but—he’s a cheater and she’s a cutthroat schemer, something Fain relishes. “I never anticipated how fun it would be to play such an edgy character—I mean, she switches the bodies of car crash victims! Let it be known I’d never do something like that,” the actress says with a laugh. Fain goes on: “In plays, I’m always the ingenue. But on TV, I’m always cast as the meaner girl. It’s become a nice balance.”

Present Happiness: Now, two years after Fain began her journey with Present Laughter, the actress is finally on Broadway, reprising a role she loves. “I can safely say this is one of the biggest events of my life,” she declares. “It’s pretty darn momentous!” Upping the ante is the fact Fain is surrounded by familiar faces from the Boston run, as well as two welcome additions: Tony Award winner Harriet Harris and stage and screen stalwart Richard Poe. “Being able to look on this time of my life and relate it to this cast specifically makes it even more special, if that doesn’t sound too corny. I’ve been dreaming of this moment since I was 12 years old, and when I look at the people around me, I know I couldn’t be in better hands.”