Ron Faber (left) and Stephen Stout (right) in Lucky Stiff. Photo by Peter Cunningham.

This episode of Settling Scores dives into the delightfully offbeat world of Lucky Stiff, the cult-favorite musical that helped launch the legendary songwriting team of Lynn Ahrens and Stephen Flaherty. With its rapid-fire wit, breakneck(!) farce, and charming score, Lucky Stiff showcases the early sparks of a musical theatre partnership that would go on to create Ragtime, Once on This Island, and Anastasia. We'll attempt to outline the show's wild plot and swoon over some lovely musical moments, all while tracing how Ahrens and Flaherty’s unique voice first took shape. Along the way, we unpack behind-the-scenes stories, creative risks, and why this small, zany musical still punches far above its weight. Call it a love letter to joyful absurdity.

Perfect for fans who like their Broadway deep dives smart, irreverent...and perhaps a little feisty!

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Stephen Flaherty and Lynn Ahrens circa 1988

Julie White and Stephen Stout in Lucky Stiff. Photo by Peter Cunningham.

New York Times review of Lucky Stiff from 4/27/1988

John Scamardella (standing) and Steve Mook (seated). Pull-Tight Players Theatre production of Lucky Stiff, 2025. Photo credit: Three Wishes Photography

Jeremy Hargis (left) and Bre Hall (right). Pull-Tight Players Theatre production of Lucky Stiff, 2025. Photo credit: Three Wishes Photography

The incomparable Mary Testa. Photo credit: Michael Kushner

Original playbill from Playwright's Horizon

The *interesting* movie version of Lucky Stiff.