You’ve seen the posters. Maybe you caught the 2023-24 Broadway revival with Jonathan Groff, Daniel Radcliffe, and Lindsay Mendez. Or maybe you're just a Sondheim nerd who’s spent way too much time dissecting the cast recording. Either way, the merrily we roll along characters are some of the most frustrating, lovable, and deeply human figures in musical theater history.
Why frustrating? Because we meet them at their worst.
The show famously runs backward. We start in 1976 with a group of bitter, wealthy, and estranged "friends" and end in 1957 on a rooftop where they’re still full of hope. It’s a gut-punch. Watching these characters "age" into innocence makes their eventual (or rather, previous) downfalls feel inevitable.
The Core Trio: Frank, Charley, and Mary
At the heart of everything are three people who promised to "change the world." Instead, the world changed them.
Franklin Shepard (The One Who Sold Out)
Frank is the engine. He’s a gifted composer who eventually stops composing to become a high-powered Hollywood film producer. Honestly, he’s easy to hate in the first scene. He’s cheating on his wife, he’s arrogant, and he’s surrounded by "The Blob"—his circle of vapid, wealthy sycophants.
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But as the clock ticks backward, we see the cracks. Frank isn’t a villain; he’s just a guy who made one "practical" compromise after another until he couldn’t recognize his own soul. He chooses the money. He chooses the fame. By the time we see him as a starry-eyed kid in the final scene, "Our Time," it’s heartbreaking because we know exactly where that ambition leads him.
Charley Kringas (The One Who Stayed "Pure")
Charley is Frank’s writing partner, the lyricist and playwright. If Frank represents commercialism, Charley represents artistic integrity—sometimes to a fault. He’s stubborn. He’s neurotic. He’s the guy who has a literal nervous breakdown on national television (the iconic "Franklin Shepard, Inc.") because he’s so fed up with Frank’s business deals.
Charley is often seen as the "moral compass" of the show, but he’s not perfect. His rigidity and inability to meet Frank halfway contribute to the death of their friendship. When he tells Frank, "Why can't it be like it was?" it’s the central tragedy of the show. You can't go back.
Mary Flynn (The One Left Behind)
Mary is the glue that didn't hold. She starts (in our timeline) as a bitter, alcoholic theater critic who’s hopelessly in love with Frank. She spent her life being the "best friend," watching Frank marry other women while she pined for him.
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Mary’s journey is arguably the saddest. She was a novelist—she wrote one great book—but she lost her spark. Her alcoholism isn't just a character trait; it’s a coping mechanism for the loss of the "old Frank" and the "old Charley." By the end of the play, when we see her as a vibrant, witty young woman moving into the same apartment building as the boys, you just want to scream at her to run the other way.
The Supporting Cast: Catalysts and Casualties
The trio doesn't exist in a vacuum. The people around them act as mirrors, showing us exactly how Frank’s life went off the rails.
- Gussie Carnegie: She’s the ultimate Broadway diva. Gussie starts as Joe Josephson's wife but eventually seduces Frank, leading to his first divorce. She is glamorous, predatory, and deeply insecure. She represents the "success" Frank thinks he wants.
- Beth Spencer: Frank’s first wife. She’s "midwestern" and wholesome, the woman Frank wrote songs for before the Hollywood lights blinded him. Her rendition of "Not a Day Goes By" remains one of the most devastating moments in the show. She’s the casualty of Frank’s ambition.
- Joe Josephson: The big-talking producer who loses everything. He starts as the guy with the money and ends (well, begins) as a pathetic man who lost his wife (Gussie) and his career to the younger, hungrier Frank.
Why the Character Arcs Still Hit So Hard
People keep coming back to these characters because they represent the choices we all face.
Do you take the high-paying job you hate, or do you struggle for your art? Do you stay loyal to the friends who knew you when you were nothing, or do you "upgrade" your social circle as you move up the ladder?
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The 1981 original production was a massive flop, mostly because audiences found the characters too unlikeable. But time has been kind to Merrily. We’ve realized that the characters aren't meant to be "liked" in the traditional sense—they’re meant to be understood.
Real-World Dynamics and E-E-A-T
Theater critics like Frank Rich and Ben Brantley have often noted that the show’s power comes from its specificity. Sondheim and book writer George Furth (who based the musical on the 1934 play by George S. Kaufman and Moss Hart) captured a very specific New York creative energy.
Mary Flynn, for instance, is often compared to Dorothy Parker—the sharp-tongued, brilliant woman who found herself drowning in gin and unrequited longing. Understanding these archetypes helps make sense of why Mary is so central to the emotional stakes; she is the historian of their friendship.
How to Deeply Understand These Characters
If you’re looking to really "get" the merrily we roll along characters, don't just watch the show once.
- Listen to the lyrics of "Old Friends": It’s the mission statement of the show. It’s about the "small things" that keep people together—and the small things that tear them apart.
- Compare the two versions of "Not a Day Goes By": Notice how the meaning changes. In Act I (1960s), it’s a song of heartbreak and betrayal. In Act II (1950s), it’s a song of pure, hopeful love. The notes are the same, but the context is everything.
- Track the "Rich and Happy" theme: Watch how Frank’s definition of "happy" shifts from creative fulfillment to literal bank account balances.
The ultimate takeaway from these characters is a bit of a warning. The show asks: "How did you get to be here?" It’s a question we should probably all ask ourselves before we reach 1976.
To see how these character dynamics play out in a modern context, your next step is to watch the filmed version of the Maria Friedman production or listen to the 2023 New Cast Recording. Pay close attention to the way Charley (Daniel Radcliffe) looks at Frank (Jonathan Groff) during "It's a Hit." You can see the exact moment the "purity" starts to slip away, and that’s where the real story lives.