- “Miss Lily St Regis, I'm named after the hotel”
- ―Lily St. Regis
Lily has proven to be quite idiotic and dumb throughout the film. Her lack of wit causes her allies Rooster and Agatha to put very little trust in her.
Lily is also very greedy. Her greed is what inspires her to help Rooster in many of his wicked plans. Her greed also causes her to ruin many plans, including the one to kidnap Annie.
Lily is also very vain. Despite being very poor, she wears very fashionable and expensive clothing. She has been accused of being a gold digger by Agatha Hannigan in the movie.
Lily's poor sense of judgment is also very prominent. She associates herself with very dangerous people in New York City. She also can't tell whether or not people are lying to her or even speaking metaphorically.
Lily has very fair skin and short blonde hair. She is both thin and short. Her makeup fits the style of the 1930's when the movie is set. She has high-arching eyebrows and very dark lipstick.
Lily wears a lavish pink coat with a white fur scarf. When she dances, she often swings her scarf around. She has a matching hat which she wears throughout the film as well. Her purse is very small and similar to a pouch.
Not much is known of Lily's early life. She is named after a popular hotel. She has most likely been conning for a long time. She and Rooster began a relationship a short time before the events of the film, and conned together before Rooster was arrested.
Role in the film
Lily is first introduced on the streets of New York City. After Rooster escaped jail by bribing the warden, he and Lily contact Agatha for money. When they meet her at her orphanage, she is pleased and surprised to see Rooster out of jail, but is annoyed by Lily whom she believes is an airhead. Lily proudly announces to her that she is named after a famous hotel, but she is only mocked further.
Furthermore, Agatha tells Lily and Rooster that she doesn't have any money to spare. Rooster becomes upset, as he has no money to give to the warden whom we bribed. Agatha adds that while the three of them are out of luck, Annie, an orphan she used to take care of, is spending the Christmas season at billionaire Oliver Warbucks's mansion.
All three of them express their annoyance at Annie's fortune. However, Rooster believes that they can use Annie's fortuity for their own gain. Lily and Agatha are overjoyed and excited by this idea. And together, they visualize a future where they live lavishly ("Easy Street").
Meanwhile, Annie is enjoying life filled with love and care. Both Oliver and his secretary, Grace Farrell, enjoy every moment with her. However, when he invites her to live with him forever as his adopted daughter, she rejects. Stating that her parents left her with a promise to come back, she expresses to Oliver and Grace that she can't give up on them. Oliver understands and begins a quest to find her parents, offering a $50,000 dollar reward to anyone who can prove they are them.
Back at the orphanage, the orphans are enjoying their favorite radio show, when they hear Annie's voice calling out for her parents. They are ecstatic to hear her and begin singing and dancing. Agatha, annoyed by them, dismisses them.
Moments later, Lily and Rooster (disguised as a poor couple) enter Agatha's office. Introducing themselves as Annie's parents, she is overwhelmed with disbelief. Lily incorrectly assumes that she truly didn't believe that they were Annie's parents. Agatha, however, states that she did fall for their trick before Lily ruined it.
Rooster tells Agatha about the $50,000 dollar reward set by Oliver Warbucks. Pretending to be Annie's parents, Lily and Rooster could successfully steal the reward money, and "dispose" of Annie. Agatha loves the idea but advises them will ruin the charade, and get them all locked away forever. Rooster agrees and decides that Agatha will play the role as Annie's mother instead by shoving Lily onto the floor. Agatha and Rooster agree that they will split the money 50/50, half for herself, and the other for Rooster and Lily. Lily is angry that she only gets 25% of the batch, but acquiesces, as she wouldn't want to be cut from the deal entirely.
On Christmas Eve, Agatha and Rooster successfully prove themselves to be Annie's parents. By hiring a man who can make fake birth certificates, and by buying a necklace similar the one that Annie's parents left to her, they fool Oliver. However, he, announces that he will not hand over Annie nor the reward money until after Christmas. Therefore, they must wait another day for their money.
On the following day, Lily is left behind at the orphanage once again, as Agatha and Rooster return to the Warbucks' mansion to collect their bounty. Lily, who spends her time playing poker with the orphans, racks up a debt of $500 dollars to the orphans. She is immediately anxious because she doesn't know where she will find the money to pay up. However, she quickly calms down, stating that she'll be living easy in no time. The orphans are bewildered by her strange comment and command her to fess up. Realizing her mistake, she says her lips are sealed on the matter, much like her lipstick. However, by holding her purse ransom, the orphans force her to tell the entire plan to them.
During Lily's confession, the orphans begin to feel anxious for Annie. Moreover, she begins to realize that Agatha and Rooster may double-cross her after they receive the money. Remembering a time when Rooster let her take the fall for another con, she realizes that she can't trust them. She and the orphans rush to the Warbucks' mansion, where they ambush a "Ralph and Shirley Mudge". They are revealed to be Agatha and Rooster, ruining their almost perfect escape.
Agatha, in a feat of desperation, nabs the $50,000 dollar check and bolts for the door. However, President Roosevelt appears in front of Agatha. Revealing all of Rooster's and Lily's several aliases, he arrests all three. Unlike Agatha, who has to restrained by several men, Lily acquiesces, and states that at least she'll be wearing silver, referring to the handcuffs being placed on her.
Differences from the Source Material
In the musical, Lily pretends to be Annie's mother instead of Agatha. This main difference is that she is given a smaller role in the film than she has in the musical and in an older film adaption. However, when she is playing poker with the orphans in the film, she decides to ambush Rooster and Agatha at the Warbucks' mansion. This scene is not included in the musical since she was posing as Annie's mother. But it gives her a role at the climax of the movie.
Daniel "Rooster" Hannigan
Although they are romantically involved throughout the film, Rooster and Lily seem to have very little attachments to each other. When introducing her to Agatha, he can't recall her last name. She has been shown to use and abuse Lily, either by using her as a scapegoat or pushing her off tables.
Lily doesn't seem to have any more feelings for Rooster than he does for her. She seems to be more interested in the money he'd be able to give to her.
There seems to be very little trust between them, as well. Rooster does not believe that she is able to help in the plot to kidnap Annie and that she'd ruin it. Conversely, Lily doubts that he would share the reward money with her, and decides to rat him out, than risk being cut out of a deal.
Agatha clearly shows distaste towards Lily. She mocks her constantly throughout the film. When planning the kidnapping of Annie, she convinces Rooster to kick Lily out of the plan, because she'd ruin it.
Lily develops a similar dislike for Agatha later on. She has very little trust that Agatha will fairly share the reward money for pretending to be Annie's parents. Because of this, she ambushes Agatha in the end, sending her to a mental asylum.
The orphans spend a small amount of time with Lily while she is left behind at the orphanage by Agatha and Rooster. During this time, she plays poker with them which she supposedly teaches them to do so. Consequently, they beat her, and she owes them several hundred dollars. She becomes angry that she could lose to children, and they state that it was beginner's luck that let them win. Because they have been known to be tricky, they might have learned to play well before she "taught" them how to play.
The orphans also torment Lily in other ways. After hearing that Agatha and Rooster at the Warbucks' mansion, they immediately become suspicious as to why they would be where Annie is. Lily attempts to stay quiet on the matter, but after they keep her purse ransom (by playing Keep Away), she relents.
Both Lily and the orphans arrive at the Warbucks' mansion at the same time, implying that they chased after the Hannigans together. However, they are obviously not allies, as the orphans cheer when President Roosevelt arrest her and the Hannigans.
- Kristin Chenoweth, who played Lily, would star along with Victor Garber, who played Oliver Warbucks, in another movie musical produced by Disney, The Music Man (2003).
- St. Regis, the hotel which Lily is presumably named after, is a five diamond luxury hotel which opened in 1904.
- Chenoweth once auditioned for the role of Annie but was turned down due to her thick southern accent. You can actually hear it in the film.
- Because of her many aliases, it's unknown whether or not Lily is her true name.
- "Miss Lily St. Regis! I'm named after the hotel."
- "Gee, I don't know!"
- "Hey, wait a minute!"
- "It ain't fair!"
- "The Oliver Warbucks, the millionaire?"