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The 2020 Broadway Radio Brainteasers By Peter Filichia

Most Sundays of the year, I can be heard on James Marino, Michael Portantiere and I discuss what we’ve seen on stage (which lately hasn’t been easy to do). The culmination of each episode has me giving a brainteaser about musicals and/or plays.

It’s become a rather popular feature, thanks to such scholars as John Baccarella, Jeremy Scott Blaustein, Greg Blazer, Brigadude, Jon Delfin, Steve Garvey, Ed Glazier, Sam Gonzalez, Josh Israel, Alex Lauer, Jack Lechner, Jake Leonard, Robert LoBiondo, Alyssa Maher and Doug Strassler (also known as Broadway’s cutest couple), Mike Meaney, Jed Slaughter, Jeff Vellenga, Cary Winslow and of course Tony Janicki, who’s usually the first to correctly answer, no matter how torturous my question may be.

Each and every April, I select some questions from the previous year and send them your way. Just in case you never or seldom tuned in, here are some of the most challenging. If you care to answer one, two or them all, email me at [email protected]. In any case, I’ll give the answers in two weeks’ time.

1—A song from a ‘60s musical mentions all five of New York City’s boroughs – but refers to Staten Island as Richmond, which was its official name until 1975. What’s the song and from which musical does it come?

2—One of Stephen Sondheim’s most famous lyrics – in a show for which he only wrote lyrics — contains two lines that became the title of a 1970s supper club revue that has received both American and British cast albums; its title song was recorded by one of our most famous recording artists. What are the two lines and the shows and the singer who first brought it to the public’s attention?

3—Of all the major Broadway songwriters, which one had the highest percentage when it came to working on musicals set in France?

4—In 1956, a musical’s opening number was precisely the same as one that opened a musical four years earlier. What is it and what were the two shows?

5—In her first starring role in a musical (one that saw a Broadway revival in this new century), this actress romanced a man whose surname is pronounced the same way as the surname of the character that she would play a dozen years later. Yes, the surnames are spelled differently, but nevertheless pronounced the same. Who’s the actress, the shows, as well as the surnames and spellings of both characters?

6—A musical set in Italy has a title song that colloquially alludes to a piece by an Austrian composer. What’s the show, the title song and the name of the Austrian composer’s work?

7—Around twenty years before this major musical hit officially opened, its composer’s father was the sole musician in a very short-lived Broadway play. It played in the theater directly behind the theater where his son’s major hit would play its entire run. What’s the name of both people, the shows with which they were connected and the theaters, too?

8—A musical written by brothers starred sisters. Who were these men and women and what was the musical?

9—What Rodgers and Hart musical got a reworking by a writer almost exclusively a lyricist who had a splendid enough career to get him into The Theatre Hall of Fame?

10—Name the songs from 110 IN THE SHADE, YOU’RE A GOOD MAN, CHARLIE BROWN and HOW NOW, DOW JONES that offer what we’ll euphemistically call alternative facts.

11—A certain 1960s Tony-nominated Best musical — that wound up winning only one Tony in another category — had a logo that actually pictured the name of the play on which it was based? What is it?

12—He wrote the novels on which two musicals were based – and in each, he’s an actual character. Who is he?

13—The name of a comic book character has been seen on the marquee two times at the same Broadway theater: once in a new musical and once in a revival of a reasonably famous classic play. Who’s the comic book character, what’s the musical, the play revival and the theater?


15—What star appeared in the original Broadway productions of one musical by Bob Merrill and two by Charles Strouse and Lee Adams?

16—A character named Vernon has appeared in two ‘50s Tony-winning musicals. One was DAMN YANKEES. What was the other?

17—What world-famous, Tony-winning musical has its first three songs start with the same letter? (A hint: when the film version was made, the fourth song in the stage score was switched with the third.)

18—A famous one-word musical that has nine letters in its title originally went by an eight-letter title. All eight letters were included in the title we know, but one letter was added up front. What was the original title and what is the now-famous title?

19—In Michael Stewart’s book for HELLO, DOLLY! he has Dolly mention a 19th century stage star who turned up as an actual character in one of Stewart’s later shows. Who is this former luminary?

20—What do these characters have in common: Lily Garland, Joe Hardy, Paul San Marco, Signor Pirelli and Sweeney Todd.

21—A novel in the ‘30s was made into a film in the ‘50s – but there the sex of the protagonist was changed from a man to a woman. When the musical version of the novel opened in the ‘60s, the protagonist was a man again – but a woman wound up stealing the show. What’s the name of the property that never changed its title and the woman who stole the show?

22—A smash-hit play of the 19th century had a character whose full name was repurposed in a Rodgers and Hammerstein hit; there, they separated his first and last names, not by a real middle one, but by a preposition. What was the play, the character’s name, the musical and the character’s expanded name?

23—The composer-lyricist of a musical that would win him a Best Score Tony in that show’s opening number actually quoted three words in six notes from a song he’d written before. Who is he, the show, the song and the song within the song?

24—A “May-December romance” refers to a relationship between a young person and an older one. What musical that involved just such a situation actually opened in May and closed in December?

25—An off-Broadway musical had a leading lady who’d win her first Tony a dozen years after her understudy in this production would win her first and only Tony. What’s the show, who’s the star, the understudy and the musicals that gave them their Tonys?

26—In BYE BYE BIRDIE, Rosie and Albert as well as Hugo and Kim are in love – and yet, the only time we hear “I love you!” it’s said by someone else. Who said it – and to whom?

27—What do these Tony-winning songwriters have in common? Lionel Bart, Jerry Bock, Marvin Hamlisch, Sheldon Harnick, Jerry Herman, Edward Kleban and Maury Yeston.

28—She appeared in a musical in the early ‘60s where she supported one of the most famous entertainers of all time. The song in which they duetted became a popular song. Before this happened, she had been married to a composer who’d later write a big ‘60s hit. Who’s she, her legendary co-star, the name of her ex-husband and the one stage musical that he composed?

30—When this musical opened off-Broadway, this song was sixteenth in the score; when the show moved to Broadway, this song became its opening number. What’s the song and the show?

31—“Lyricists love cleverness,” William Goldman wrote in his landmark book THE SEASON before mentioning “‘uppity’ rhyming with ‘cup of tea.’” Ironically, one of the musicals in that 1967-68 season of which he wrote did have a song in which “uppity” rhymed with “cup of tea.” What’s the song and the show from which it came?

32—When the original cast album of this now-famous and often revived – but NOT Tony-nominated – musical was released, its two stars were above the title. Some years later, the recording was reissued with a new cover, but then the two stars were joined above the title by a third, even though he’d only been fifth-billed on the original jacket. What’s the show and who are the three stars?

33—What musical that ran fewer than two weeks on Broadway had an opening number that became a Grammy-winning, Number One hit?

34—Three performers got together to sing a Kander and Ebb song in one of their musicals. One performer had already won a Tony; one would soon win a Tony; and one had to wait quite a few years for a Tony. Who are the three, what’s the song and the musical?

35—What do Alvin, Bernie, Charlie, Ezekiel and Wilmer have in common?

36—Many a musical movie that has later become a stage musical on Broadway uses the film’s most famous songs in its overture. But what overture that’s more than three minutes long has no songs from its famous film?

37—Two Best Musical Tony-winners that won their prizes nine years apart both start their overtures in the same but most atypical way. Explain why, while also naming the musicals.

38—For the same show, he was nominated as Best Actor in a Musical and she was nominated as Best Actress in a Musical. Each had already won a Tony. And yet, together they had less to sing than two people who are heard more often on the original cast album – two people, in fact, who had never before appeared on Broadway and never would again. The two nominees, however, would make other Broadway appearances. What’s the show in question and who are the two stars? (You needn’t name the two nobodies unless you really want to.)

Take those, Ken Jennings and James Holzhauer!

Peter Filichia also writes a column each Monday at and each Friday at He can be heard most weeks of the year via