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  • Adaptation Displacement: The musical and its adaptations are better known than the original comic strip these days. For later revivals, Thomas Meehan even changed one line in the script from "Next thing you know, she'll be in the funny papers" to "Next thing you know, they'll make a musical about her."
  • Alternative Character Interpretation: Why did Miss Hannigan keep the truth about Annie's parents' death from her? Did she prefer to encourage the idea that her parents had forgotten her? Did she plan to tell her someday and crush her hope for good? Or did she secretly want to keep Annie's hope alive, however much Annie bugged her?
  • Aluminum Christmas Trees: Why on earth does the radio show have a ventriloquist act? Surely that's ridiculous. Well maybe, but that really happened.note 
  • Award Snub: At the Tony Awards, the original Broadway production won every major creative award except for Best Director, which went to a now-obscure musical called I Love My Wife. Because Mike Nichols was the producer of Annie, it was widely suspected that he and not Martin Charnin had directed the show, which may have contributed to Charnin's snub, but a critic who saw a tryout performance before Nichols came on as producer has said there was "no discernable directorial difference" between Charnin's early version and the one that opened on Broadway, while both Nichols and Charles Strouse have said that Charnin was sole director.
  • Awesome Music: "Maybe", "Tomorrow", "NYC", "Easy Street"...
  • Broken Base: Not counting the 1930s adaptations (which were based on the comic strip, since the musical hadn't been written yet), many would often argue as to which film adaptation deserves more credit - is it the 1982 original, the 1999 remake or the 2014 modernised reboot? Though many would definitely agree that the one starring Aileen Quinn is the one that's most fondly remembered.
  • Common Knowledge: It's often been said (and was formerly written on this very page) that in Amanda Dehnert's notorious Darker and Edgier production for the Trinity Repertory Theatre in 2003, Annie woke up back at the orphanage in the end, turning the happy ending into a Downer Ending. But while it did have an All Just a Dream finale (until Martin Charnin disapproved, that is), Annie didn't wake up back in the orphanage: she woke up in an abandoned theatre, where she had wandered and fallen asleep after running away from the orphanage, and in a Bittersweet "Ray of Hope" Ending, she sang a reprise of "Tomorrow" and then left with Sandy in search of a new life. It wasn't as entirely bleak as legend has it.
  • First Installment Wins: Of the three adaptations based on the play, the 1982 film is the most well-known and popular adaptation.
  • Hilarious in Hindsight: One of the starting outfits in Hitman (2016) is a tuxedo for Agent 47, which would be surreal for fans of the Annie franchise. As a result of both 47 and Warbucks displaying an affinity for expensive suits, some would joke about 47 being Daddy Warbucks or the other way around.
  • Harsher in Hindsight: It so happened that in 2012, a major hurricane named "Sandy" struck New York City and caused significant damage, at the very same time a 35th anniversary revival of Annie was opening on Broadway. It didn't take long for some to make references to the comic strip and musical, specifically Sandy the dog.
  • Jerkass Woobie: Miss Hannigan, who drinks on the job to relieve the stress. And consider the time she lives in; it gives her a double-whammy of disadvantages: not only is there a depression, but her gender would severely limit her job options as well. Basically, she has no option but to work a job that she's completely unsuited for. On top of that the orphans take joy out of making her life miserable and while this isn't entirely unjustified, it does explain her attitude towards them in her song "Little Girls".
  • Just Here for Godzilla:
    • A decent amount of people who don't care for the cutesy show will admit to enjoying the much more mean spirited character of Miss Hannigan.
      • In fact in the UK the actress playing Miss Hannigan is given the Guest Star Billing because she is often played by a celebrity.
    • Meanwhile, some who aren't into the show will still admit it has some very good songs which are worth a listen.
  • Love to Hate: Miss Hannigan is easily the most popular character in the show due to being such a hilarious bitch. The fact that she's got some of the best music in the show only helps.
  • Overshadowed by Controversy: A particularly infamous controversy surrounded the 20th anniversary revival from 1997. A nationwide, publicized contest was held to cast the title role, with thousands of young performers lining up to audition for the coveted lead. The role was eventually given to 12-year-old Joanna Pacitti, who headlined the show throughout its national tour. Weeks before the production hit Broadway, however, Pacitti was taken out of the show because the producers felt that her performance (and chemistry with the cast) was not meeting their expectations. News of the girl's firing spread throughout the nation, and received even more attention after it was covered on ABC's Turning Point, the same program that publicized the contest and Joanna's initial casting. Though it was a heartbreaking experience for the young actress, she would eventually find new work thanks to the public exposure, and she even got to reprise the role of Annie for a regional production of the show.
    • This same revival had Nell Carter as Miss Hannigan. She even got a extra song. However she was upset to see commercials were using Marcia Lewis note , a white actress, instead of her. Nell reported it to the producers who claimed expense was the reason. However, she felt that Race had been behind it. In the end it she understood the money problems to reshoot, but she was replaced by a white actress (Sally Struthers) before this troubled revival ended after 239 performances.
  • Questionable Casting: The live show casting Tituss Burgess as Rooster raised its share of eyebrows given the character is pretty much the exact opposite of the actor's repertoire.
  • Retroactive Recognition: Many, many actresses got their start in some production of Annie. To list them all would probably double the page size, but a few notables:
  • Sequelitis: Twice if you can believe it
    • Annie 2 starring Danielle Findley as Annie (and Annie 2, at that), which got heavy interest (read: advance $ale$) from people who wanted to revisit Annie... until it opened. In the end, the creators chose not to subject Broadway to what had gotten silence from angry theater-goers at Kennedy Center, even after alterations.
      • Reading the plot to this musical explains a lot, it's subtitled as Miss Hannigan's Revenge note , the story is that Warbucks is told by a Child Welfare Commissioner that he needs to marry to finalize the adoption of Annie and feeling that Grace is too young, decides to find a wife closer to his age. Miss Hannigan escapes from prison, and with the help of some cons, becomes the perfect wife; with her background knowledge of Annie, she passes the tests, but realising that Annie will have to approve her causes her to almost quit. However, she finds a street girl that looks like her and she was about to get away when Grace realises the truth and saves Annie from death. Miss Hannigan is exposed and is handcuffed away with her gang, Grace shows Oliver that she is suitable, he marries her and Annie gets her happy ending.
      • The reason for its failure was partly because it had the worst case of an idiot plot, while the original had a conclusion that worked. Also, Warbucks is friends with FDR, so surely he could bend the rules so he could do a single parent adoption. Miss Hannigan's revenge plot made no sense, as she commited fraud and was caught, while Annie did nothing to deserve revenge.
    • Then a second sequel called Annie Warbucks, which has done a little better but stayed off-Broadway; a transfer to Broadway was planned, but the backer pulled out.
      • The show uses the marriage for adoption plot from the former sequel, but the Child Welfare Commissioner Harriet Doyle is using it to make her daughter Sheila Kelly his wife and rob him of his fortune; however, Annie and Grace end up playing a trick at the wedding, causing Doyle and Kelly to expose themselves and Warbucks to express his feelings for Grace and the happy ending once more.
  • Signature Song: "Tomorrow" with "Maybe" coming in second place.
  • Special Effect Failure: Harry Connick Jr.'s bald wig in the NBC telecast proved unconvincing to most viewers.
  • Sweetness Aversion: While it's part of the charm for fans, the main issue critics take with the show is it being sickeningly sweet with fairly little conflict to disrupt this.
    • That said, during the show's first previews at the Goodspeed Opera House in East Haddam, Connecticut, the child actress who originally played Annie, Kristen Vigard, was let go because she came across as too sweet in the role. The production team decided they needed a tougher, more streetwise Annie, so Andrea McArdle, who was originally cast as Pepper, was promoted.
    • In 2003, Amanda Dehnert directed a production for Trinity Rep in Providence, Rhode Island which was a lot darker than usual, playing up the harsh Depression Era setting and averting most of the usual sweetness. However, it had a reworked ending, which had Annie waking up and realizing that the happy ending was All Just a Dream. Martin Charnin saw one of the early previews and wasn't happy with the negative impression, so the ending was deleted. However, Charles Strouse saw it, enjoyed the reworking and asked Dehnert to produce his new musical.
  • Tear Jerker:
    • "So maybe now this prayer's the last one of its kind...won't you please come get your baby...maybe..."
      • The fact the orphans all sing Maybe hints that even Pepper who will soon be too old and might have to leave still wishes for adoption.
      • The 1982 film's Orphans Reprisal is just heartbreaking.
    • Annie's reprise of Maybe when she prepares to leave with the Mudges on Christmas Day of all days.
    "Silly to cry
    Nothing to fear
    Betcha New Jersey’s as nice as right here
    Betcha my life
    Is gonna be swell
    Looking at them
    It’s easy to tell
    And maybe I’ll forget
    How nice he was to me
    And how I was almost his baby
    Maybe"
    • In the 1982 film, Grace telling Annie that they haven't found her parents yet, as a sad melody of Maybe is played. Annie sadly walks away, and a disgusted Grace tells Warbucks the amount of people that came and yet they knew nothing of locket saying about how terrible people could be.
    • Warbucks' reprise of "Maybe" in the 1982 film:
    "And I know I'll forget
    How much she meant to me
    And how she was almost my
    Baby
    Maybe."
    • The finale of the 2021 adaptation, in which Annie and some modern-day children sing "Tomorrow" a capella.
    • The 2023 UK Tour had Paul O'Grady playing Miss Hannigan, a part he had done years before. It would be the last thing he did, Paul died 10 days after he finished the Edinburgh part of the tour, Tommy Wade-Smith who was in the cast had a TikTok, where he chatted with Paul during rehearsals and he managed to capture one of Paul's last curtain calls. The tour carried on to Liverpool, where Paul was meant to play Hannigan again but instead, Craig Reveal Horwood played it and dedicated the performances to Paul's memory.
  • Values Dissonance: In the show's original book, Miss Hannigan spanks Annie with a paddle onstage when she catches her trying to run away. Thomas Meehan later revised the script to cut this part, as do all the film versions, since by post-'70s standards it's less "family friendly" to see a child being hit, even by a villain.

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