- Adaptation Displacement: The musical and its adaptations are better known than the original comic strip these days.
- Crowning Music of Awesome: "Maybe", "Tomorrow", "NYC", "Easy Street"...
- Ear Worm: "Tomorrow".
- "You're Never Fully Dressed Without a Smile", as well, much to the irritation of a number of people who've been in the show. This particular troper was in a production and still can't get it and Tomorrow out of her head.
- Hilarious in Hindsight: "Some women are dripping with diamonds, some women are dripping with pearls..."
- 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.
- Moral Event Horizon: Rooster crosses it big-time at the end of the 1982 movie, when he attempts to murder Annie in a fit of rage.
- 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:
- Sarah Jessica Parker as a Broadway Annie.
- Molly Ringwald as an orphan in a West Coast production.
- The documentary Life After Tomorrow, though mainly interviewing former orphans that dropped out of the spotlight, had a few recognizable faces, including MSNBC anchor Dara Brown, Martha Byrne, Senta Moses, and Joanna Pacitti.
- Sequelitis: 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.
- Tastes Like Diabetes: The 1982 film, which is notoriously corny.
- Tear Jerker: "So maybe now this prayer's the last one of its kind...won't you please come get your baby...maybe..."
"And I know I'll forgetHow much she meant to meAnd how she was almost myBabyMaybe."
- Warbucks' reprise of "Maybe":
- Values Dissonance: Considering that Harold Gray killed off Warbucks when FDR took office because of his fervent opposition to his policies, he likely wouldn't be taking the prospect of Warbucks praising the New Deal well.