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Hilarious In Hindsight / Theatre

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  • Conversations With My Father, David Krumholtz stars as a younger version of Charlie, which is also the name of his character on NUMB3RS, which also stars Judd Hirsch.
  • Beatrice's line, "No, not 'til a hot January" in Much Ado About Nothing sounds somewhat ridiculous to anyone in the Southern Hemisphere (except maybe Antarctica). It's even funnier, and maybe a little less ridiculous, when you realise she's talking about getting along with Benedick.
  • The entire "We Need a Little Christmas" number in Mame. The entire point of the scene is that the characters are at such a low point in their lives that they decide to cheer themselves up by starting their Christmas decorating early, even though, to quote the lyrics, "it's one week past Thanksgiving Day now". Now that retailers have extended the holiday season to well before Thanksgiving, it's hard to see how Mame and co. are rushing into things; if anything, they're dogging it.
  • Early on in Act II of Iolanthe, the Fairy Queen sings of Captain Shaw (London's fire chief at the time and a fan), and in the premiere she stretched out her arms towards him while singing "Oh, Captain Shaw! Type of true love kept under!". A few years later, Shaw was mixed up in a messy adultery scandal.
  • Nick Jonas playing Marius in Les Misérables opens up an entire can of recursive funny at Eponine's expense. The first is, obviously, her Stalker with a Crush status making her the original Jonas Brother fangirl; the second, she has a crush on her brother. (For those of you not in the know, Nick Jonas originally played Gavroche in Les Mis.)
  • In Bell, Book and Candle, Shep refers to himself as having been "bewitched" — "I didn't say I meant it literally." Guess what Fantastic Comedy Bell, Book and Candle inspired?
  • In Sweeney Todd: The Demon Barber of Fleet Street, Mrs. Lovett calls the title character "Mr. T." Pity the fool...
  • In the 2003 revival of Tell Me on a Sunday, the girl tells her mother that the latter "managed very well going from vinyl to CD" in an effort to urge her to get online and write emails instead of letters in the post (blatant use of the latest technology and references to modern pop culture were the main ways the show was updated for the revival). Now CDs are essentially obsolete, while vinyl is enjoying a resurgence of popularity.
  • Towards the end of Rosencrantz and Guildenstern Are Dead, there's a lot of talk about being, or not being, On A Boat.
  • In the 2008 concert revival of Chess, Idina Menzel plays Florence, signing the line "a battleground for rival ideologies to slug it out with glee". Fast-forward a couple of years, and she's actually on a TV show called Glee.
    • That performance of Chess also features Kerry Ellis as Sveltna, Forence's romantic rival. Both Menzel and Ellis have portrayed Elphaba in Wicked onstage.
  • Wicked: Speaking of Idina Menzel and Wicked, since Idina starred in Frozen, people can't help but notice how many parallels Queen Elsa has to Elphaba.:
    • In Wicked, Elphaba is a misunderstood older sibling, has magical powers, has a dramatic "I Am Becoming" Song ("Defying Gravity"), and stars alongside a blonde-haired actress whose first name is Kristin. In Frozen, Queen Elsa is a misunderstood older sibling, has magical powers, has a dramatic "I Am Becoming" Song ("Let it Go"), and starring alongside a blonde-haired actress whose first name is Kristen. Coincidence? Well, maybe, but that doesn't stop it from being both hilarious and awesome.
    • When Glinda confronts Elphaba near the end and says "I mean they're just shoes... let it go!". Try to hear that now without mentally playing "Let It Go" in your head.
    • One part of "No Good Deed" goes, Is that all good deeds are/When looked at with an ice-cold eye.
    • In "What Is This Feeling?", Elphaba pins Galinda's personality down to one word: "Blonde". What is Elsa? Blonde.
    • A Disney Animated Canon version of Wicked will likely never happen but fans have noticed both Idina Menzel and Kristin Chenoweth have appeared in Disney films — Menzel as Elsa from Frozen and Chenoweth as Maleficent from Descendants. Jokes about Elphaba being a hero and Glinda taking a Heel–Face Turn have popped up.
    • Caissie Levy, the first actress to play Elsa in the Broadway musical adaptation of Frozen, also used to play Elphaba on Broadway, as did Caroline Bowman, the first actress to play Elsa in the national touring production. Meanwhile, Patti Murin, who originated Anna on Broadway, was Glinda on Wicked's first national tour.
  • In the 2011 theatrical adaptation of Frankenstein, Jonny Lee Miller and Benedict Cumberbatch alternate the roles of Victor Frankenstein and the Creature. At the time, Cumberbatch was already playing Sherlock Holmes on Sherlock, and now Miller is playing the character as well, in the American TV series Elementary.
  • In the play The Seven-Year Itch, Dr. Brubaker complains about his publisher retitling his book Of Sex and Violence and giving it a lurid cover "making Meyerheim's victim—all of whom incidentally, were middle-aged women—resemble in a number of basic characteristics, Miss Marilyn Monroe." This line was omitted from the film version, in which Monroe played a quite different role.
  • Take the line "Donald Trump and I on the links, and he's my caddy" from "96,000" in In the Heights. When it was written in the mid 2000s, Donald Trump was a "generic rich guy", especially to the people of Washington Heights. A decade later, we have President Donald Trump, who is known for his anti-immigration policies (almost all of the characters are immigrant or immigrant-born), tenuous race relations with Latinos and African Americans (all the characters are Latino, except for Benny, who said the above line, who is black), and for taking many, many weekends off to golf. The idea of him being the caddy of African-American, friend-of-immigrants Benny became about 20x funnier.
    • Also, putting the show in the Washington Heights. Lin-Manuel Miranda's next show, Hamilton, prominently features George Washington as a character - and his role was originated on Broadway by Chris Jackson, who played Benny in In The Heights.
  • A few, in universe, in The Drowsy Chaperone, usually having to do with how poorly the Show Within a Show has aged:
    • The Man in the Chair notes that a rainy November is a laughable thought nowadays, thanks to global warming.
    • The back of the record advertises "Mix-ups, mayhem, and a gay wedding!". The Man in the Chair is quick to say that "Back then, gay meant fun!"
    • The Drowsy Chaperone was said to have played in the Morosco Theatre on Broadway. When the show itself went to Broadway, it opened in the Marquis Theatre, which was built on the same ground as the Morosco Theatre was.
  • In My Fair Lady, Henry's mother advises him not to talk politics and to "stick to two subjects: the weather and your health". These days, with increased political polarization, not even the weather (climate change) and health (the anti-vaxxer movement) are immune from heated debate.
  • The short-lived Broadway musical Smile has one of the characters, Doria Hudson, sing an "I Want" Song about visiting Disneyland. The Smile lyricist, Howard Ashman, and Doria's actress, Jodi Benson, would collaborate with Disney only a few years later, on The Little Mermaid. Naturally, Benson's character, Ariel, eventually "made her home in Disneyland" through several attractions and entertainment.