History Theatre / Annie

* JerkWithAHeartOfGold: Pepper. She beats up July for defending Molly, makes fun of Annie's note, and engages in a minor KickTheDog moment when she tells Molly that [[BrutalHonesty "we ain't got mommies and daddies. And we ain't ever gonna have 'em. That's why we're called orphans."]], but on the other hand, she is happy for Annie along with the rest of the girls when the latter is allowed to go to Warbucks' home for Christmas, and assists the other orphans in foiling the villains' plot.

* {{Jerkass}}: In addition to Rooster and Miss Hannigan, Pepper is one as well. She beats up July for defending Molly, makes fun of Annie's note, and engages in a minor KickTheDog moment when she tells Molly that [[BrutalHonesty "we ain't got mommies and daddies. And we ain't ever gonna have 'em. That's why we're called orphans."]] Possibly subverted as she is happy for Annie along with the rest of the girls when the latter is allowed to go to Warbucks' home for Christmas, and assists the other orphans in foiling the villains' plot.

* TheBrainlessBeauty: Lily St. Regis[[hottip:*: "Named for the hotel!"]]

* IronicEcho: Miss Hannigan makes the orphan girls say "I love you, Miss Hannigan" all the time. Later, as she and Rooster are leaving the Warbucks mansion with Annie in tow, pretending to be her parents, the girls arrive at the door just in time to expose her true identity by shouting, ''"We love you, Miss Hannigan!"''

** The girls proceed to force Lily to spill the beans, then trick her into [[TooDumbToLive going to the Warbucks mansion and demanding her share of the money from her cohorts.]]

** The girls proceed to make Lily spill the beans, then trick her into going to the Warbucks mansion and demanding her share of the money from her cohorts.

* NiceJobFixingItVillain: When the orphans are left in the care of Lily St. Regis, they trick her into revealing the Hannigans' scheme.

* {{Jerkass}}: In addition to Rooster and Miss Hannigan, Pepper is one as well. She beats up July for defending Molly, makes fun of Annie's note, and engages in a minor KickTheDog moment when she tells Molly that [[BrutalHonesty "we ain't got mommies and daddies. And we ain't ever gonna have 'em. That's why we're called orphans."]]

* IronicEcho: Miss Hannigan makes the orphan girls say "I love you, Miss Hannigan" all the time. Later, as she and Rooster are leaving the Warbucks mansion with Annie in tow, pretending to be her parents, the girls arrive at the door just in time to expose her true identity by shouting, "We love you, Miss Hannigan!"

* NiceJobFixingItVillain: When the orphans are left in the care of Lily, they trick her into revealing the Hannigans' scheme.

* NiceJobFixingItVillain: The orphans manage to trick Lily into revealing the Hannigans' scheme.

* ImpliedDeathThreat: Downplayed.
-->'''Annie:''' ''(to Pepper after she makes fun of Annie's parents' note)'' Do you wanna sleep with your teeth ''inside'' your mouth or ''out?''

* DeniedFoodAsPunishment: Right after ''You're Never Fully Dressed Without a Smile''

* {{Jerkass}}: In addition to Rooster and Miss Hannigan, Pepper is one as well. She beats up July for defending Molly and engages in a minor KickTheDog moment when she tells Molly that [[BrutalHonesty "we ain't got mommies and daddies. And we ain't ever gonna have 'em. That's why we're called orphans."]]
* TeamMom: Annie is this for the orphan girls.

* CatchPhrase: In-universe, "I love you, Miss Hannigan" is forced onto the girls by Miss Hannigan in the 1999 film.
* ConflictKiller: The 1999 film opens with Annie breaking up a fight between July and Pepper.
-->"Lay off July! If Hannigan wakes up, she'll get sore!"

* TeamMom: Annie is this for the orphan girls in the 1999 movie.

* IllegalGuardian: Rooster Hannigan and Lily St. Regis pretend to be Little Orphan Annie's "real parents" to scam reward money out of Daddy Warbucks.

* TeamMom: Annie appears to be this for the orphans in the 1999 movie.

* IronicEcho: Miss Hannigan punishes any orphan she suspects of being dishonest: "What's the one thing I've taught you? Never tell a lie!" At the end, as Miss Hannigan is being carted away by the authorities, she pleads with Annie to witness that she's treated the orphans well; Annie's response is to apologise and remind her that there's one thing she's taught them...