The Drowsy Chaperone

The Drowsy Chaperone is a musical which opened on Broadway in 2006, described by the Tagline as "a musical within a comedy". The frame story is about a lonely man named..."Man In Chair", who lives alone with his record collection. One day he feels blue, and so puts on a record from the 1920s - The Drowsy Chaperone. The majority of the musical is the record itself, with comments interjected now and then from the Man to...somebody.

The story of The Drowsy Chaperone is about the wedding of Janet van der Graaff and Robert Martin. Janet has doubts about her feelings towards Robert, and so disguises herself as a French woman and seduces him into kissing her. Of course, Hilarity Ensues as she confronts him about this kissing. Along the way, various other characters end up with marriages that they may or may not want, forcing best man George to arrange 4 marriages when he had originally only planned on one. Then a plane flies in, and they all get married and go to Rio!

...It Makes Sense in Context. Sort of.

For a more detailed plot, see The Drowsy Chaperone's page on The Other Wiki.

As a result of its premise, Drowsy Chaperone has more Lampshade Hanging than a hardware store, usually (but not always) provided by the Man In Chair.

Tropes used in The Drowsy Chaperone include:

Affectionate Parody: Of the Jazz Age, and musicals in general.
All Musicals Are Adaptations: In-universe. The booklet in the CD case for the recording mentions that the show is based off of a short story called Honeymoonin' To Do.
Ambiguously Gay: The Man in Chair. He lampshades it several times.
- Though some productions play him as merely metrosexual.
Analogy Backfire: the song "Love Is Always Lovely in the End", in which the singer, Mrs. Tottendale, is blissfully oblivious to the fact that every couple she mentions in the song (Romeo and Juliet, Henry VIII and Anne Boleyn, Samson and Delilah) had an unhappy ending. Underling tries to point this out to her, to no avail.
Aren't You Going to Ravish Me?: The Chaperone during "I Am Aldolpho."
Asian Speekee Engrish: There's an entire joke about a "rady" and a man.
Better Than a Bare Bulb: The Musical!
Big "What?": Aldolfo. What?
BSOD Song: 'Bride's Lament'.
Busby Berkeley Number: 'The Bride's Lament', according to the Man in Chair, is "a little Busby Berkeley, a little Jane Goodall."
Cape Swish: Adolpho does this. A lot.
Character Blog: During the Broadway run, the Man in Chair posted a series of videos wandering around Times Square, commenting about theatre.
Deadpan Snarker: The Chaperone, Underling, Feldzeig, and Man in Chair all fit this trope at one time or another.
Deliberate Values Dissonance: Hoo boy, Message From A Nightingale.
Deus Ex Machina: Trix flies into the wedding right after they realize they need a minister, and marries all four couples.
The Ditz: Both Kitty and Miss Tottendale.
The Family for the Whole Family: It's hard to take the gangsters seriously when their "weapons" are cooking utensils and everything they say is an Incredibly Lame Pun.
Fourth Date Marriage: Janet and Robert, to the point where "fourth date" might be an overstatement...
Funny Foreigner: Adolpho.
- Twice.
Genre Savvy: Man In Chair.
High Hopes, Zero Talent: Kitty desperately wants to replace Janet, despite her complete lack of talent and very low intelligence.
Hypocritical Humor:
- In the opening monologue, Man In Chair mentions that he hates when musicals break the fourth wall. Guess what the entire point of the show is.
- Man In Chair keeps telling the audience to "keep the magic alive" when something interrupts the play. Even if he's the one interrupting.
- 'Show Off': Janet spends the entire song showing off to her fans and the audience, complete with an encore, while singing about how she's leaving show business.
- In the intermission monologue the Man In Chair delivers, he complains about people opening crinkly candy wrappers. He then proceeds to open and eat a protein bar.
"I Am" Song: 'I Am Adolpho' - hard to get clearer than that.
Insane Troll Logic: Basically how the cast decides how Trix qualifies as a substitute minister. It boils down to; (1) Sea captains can marry people on their ships + (2) Pilots can be be equated with a captain + (3) Planes are technically (air)ships = Trix is a captain of her (air)ship and can do the marriages.
Irrelevant Act Opener: Justified in the case of 'Message From A Nightingale', as Man In Chair accidentally put the wrong record on.
The Jeeves: Underling.
Just for Pun: Pretty much the existence of the two Gangsters.
Lady Drunk: The titular Chaperone.
Large Ham: Adolpho, and by extension, his actor.
- Quoth the Man In Chair: "He was the man of a thousand accents...all of them insulting."
Last-Minute Hookup: All of the characters, including Pair the Spares.
Latin Lover: Adolpho thinks he's this, but in reality he's more of a Casanova Wannabe.
Lemony Narrator: The Man in Chair, in spades.
Letting the Air Out of the Band: A blackout happens right before the last note of 'I Do, I Do, In the Sky'
Married At Sea: Parodied. In the finale, the cast decides that the captain of an airship can marry people, as they forgot a minister.
Mood Whiplash: There are a number of funny or touching scenes interrupted by the Man in Chair giving a glimpse into his (rather sad) backstory. The biggest by far is the rather funny scene where Drowsy is telling Janet to "L-ve while you can." While Man In Chair's accompanying monologue has some funny lines, it is on the whole rather sad.
Musicalis Interruptus: The Man in Chair's phone rings, interrupting George's tap dance going into the next scene.
My Name Is Not Durwood: The Chaperone initially calls Adolpho "Adolface".
Narm: Played with in-universe in "Bride's Lament". As The Man in the Chair says, "Try to ignore the lyrics." They're about...monkeys. Yeah.
- Considering the way he sings along to this song, though, he may have come to see them as Narm Charm, especially considering his backstory.
No Fourth Wall
No Name Given: The Man in Chair, the Drowsy Chaperone, Underling, and the Gangsters.
- I was under the impression that Underling was his first name. Mrs. Tottendale, on the other hand, never has one.
Nostalgia Filter: The way the Man In Chair views the 1920s.
Only Sane Man: Underling.
Out-of-Genre Experience: The beginning of the second act.
Pigeonholed Voice Actor: According to Man In Chair, the fictional actress who played the Chaperone was typecast as an alcoholic.
Pungeon Master: When it comes to this trope, the gangsters really take the cake! ...I'm so sorry.
Porn Without Plot: Invoked by Man In Chair in a monologue about the Show Within a Show's plot.
Show Within a Show
Silly Love Songs: 'Love is Always Lovely in the End'.
Spit Take: One scene consists of nothing but spit takes. Poor Underling!
Stocking Filler: The Chaperone, usually.
Tempting Fate: After 'Show Off' "ends".

Kitty: I'm surprised she didn't do an encore.
Janet: I don't want an encore no more!

Too Dumb to Live: George stops Robert from tap dancing because he could sprain his ankle. Instead he tells him to go rollerblading. Blindfolded.
- Naturally he then sings "I'm an Accident Waiting to Happen."
Weddings for Everyone: How the Show Within a Show ends.