Nine and a half years ago, tucked away in the tiny Connelly Theater at the further reaches of the Lower East Side, The Prospect Theatre Company premiered a dazzling new musical – full of wit, intelligence, cleverly written theatre songs and dynamic staging – suggested by F. Scott Fitzgerald‘s semi-autobiographical debut novel This Side of Paradise.

The Pursuit of Persephone had its flaws, but they were flaws of ambition overshadowed by the evening’s exceptional display of musical theatre craft and freshness; a story set in the years just before this country’s entry into The Great War that stayed true to its era but showed a contemporary understanding of the unique storytelling qualities of the American musical.

Peter Mills (book, music and lyrics) and Cara Reichel (book and direction) have been responsible for high points in several theatre seasons since then (Iron Curtain, The Rockae) but Persephone, and the promise of what it could be, remains their zenith.

Retooled and renamed The Underclassman, their smart and fizzy charmer has reached Times Square’s Duke on 42nd Street in a limited Off-Broadway run that, sadly, ends the day this review is posted. Slightly less daring, but smoother in delivery, The Underclassman has its minor second act quibbles but is still vastly above all but a handful of musicals that have had major New York productions since, well, The Pursuit of Persephone.

Less of a romance than a musical comedy of manners, the narrative begins with Fitzgerald’s sophomore year at Princeton, where his interest in studies takes a back seat to his interest in writing a musical for the college’s all-male traveling theatre troupe, The Triangle Club.

For the sake of artistic inspiration, he takes up the challenge of meeting Ginevra King, considered by Ivy Leaguers to be one of the country’s four most desirable debutantes. (A title she plays for all it’s worth.) Being a relatively poor artist with no financial prospects beyond what talent and luck can provide, he sees himself as the lowly Hades pursuing the goddess Persephone. (Which winds up being the subject of the musical he writes.)

Because of distance and social standards, Scott and Ginevra have spent, as one character points out, less than 24 total hours with each other before becoming a serious item. Their relationship is sustained through regular correspondence but, as explained in one of the many clever musical scenes, letter writing in their social circle is not exactly an expression of honest emotions, but more of a courtship game with its own rules and strategies.

When we see the two together, they are surely falling in love with something; perhaps the youthful urge to feel something as poetic and romantic as described in the literature they read. But while Ginevra is drawn to the rebellious act of taking up with a poor scribe, she’s also wary of giving up her accustomed lifestyle.

Since real life provides the well-known ending, it’s not giving anything away to reveal that all F. Scott Fitzgerald gains from the affair is what he sought out in the first place, artistic inspiration. Who knew at the time that her artistic inspiration would motivate him to write an era-defining novel?

Though Mills’ score contains hat tips to the styles of upcoming composer/lyricists of the day, like Irving Berlin and Cole Porter, and a muscular rag of Scot Joplin’s ilk, the character-driven words and music stress immediacy over nostalgia. He saves the pastiche for the Gilbert and Sullivan and Offenbach salutes performed by The Triangle Club.

Surprising, but oh-so-right rhymes populate his lyrics, but they contain the kind of cleverness that’s appropriate for the people he’s writing for. So when Ginevra rhymes her own name with “clev’ra,” or when Scott improvises a love song where the melody is dictated by the notes mentioned in the lyric (“Improvising in the key of A flat / Thinking how it’s gonna be / When the two of us are sharing a flat / Residents of NYC.”), it’s the characters who are showing off, not the wordsmith.

The multiple musical gems are enhanced by Reichel and choreographer Christine O’Grady’s smart and imaginative staging, highlighted early in Ginevra’s “To Beat The Band,” where she twirls through a dance card full of potential suitors while singing of her carefree lifestyle and a drag can-can by the Triangle boys that’s danced for skill instead of laughs.

Matt Dengler makes for a gutsy, empathetic Scott with a charmingly impish humor. Jessica Grové, repeating the role she played at the Connelly, mixes sophomoric worldliness with giddy girlishness and sings and dances up a storm as Ginevra.

Another Connelly vet, Piper Goodeve, is terrifically wry as Scott’s high school sweetheart who is now Ginevra’s best friend, especially when matched with the droll Billy Hepfinger as Edmund Wilson, Scott’s pal who later becomes the noted literary critic. Fine work is also done by Marrick Smith, who nicely underplays his affection for Scott as poet John Peale Bishop.

The Underclassman is set in an era when people would go to Broadway to enjoy the musical theatre offerings the best emerging artists had to offer. This is no longer the case, as season after season Off-Broadway’s musicals show superior craft, talent and inventiveness. The Underclassman is among the best in all three categories.