Rooster and Lily St. Regis

"Rooster, you reprobate!"

- Miss Hannigan furious at Rooster for attempting to have Annie killed

Rooster and Lily St. Regis are the secondary, later true main antagonists of the musical, Annie and the 1982 film adaption. In the 1982 Columbia theatrical film version, Rooster was played by Tim Curry (who later played many other villains he voiced like Drake, Maestro Forte, Hexxus, Ben Ravencroft, Taurus Bulba, Professor Calamitous and etc. and played Dr. Frank-N-Furter, Long John Silver, and Pennywise the Dancing Clown) and Lily was played Bernadette Peters. In the Disney version, Rooster was played by Alan Cumming and Lily was played by Kristin Chenoweth.

In the 1982 version, Rooster is a con artist and he has escaped from prison, and he and his new girlfriend pay his sister Agatha Hannigan a visit hoping to get money from her, she didn't then he stole from her, Lily stole some stuff but she caught her. They intend to use the situation that Annie is at a billionaire's house for wealth, but without knowledge. Lily and Rooster pretend to be the Mudges, Annie's parents, successfully. At the end, Annie escapes and rips up the check. Rooster wants to kill her. Miss Hannigan tries to stop him, but then he punches her then goes on to try to kill Annie. Rooster is about to catch Annie (who has escaped onto the drawn B&O Bridge). When Rooster slides back down (due to Punjab knocking him after catching Annie), Miss Hannigan redeems herself and beats him with her purse. Rooster and Lily are then arrested.

In the 1999 film version, Miss Hannigan and Rooster (pretending to be Annie's parents, the "Mudges," after cutting Lily off the deal) try to get her, but Lily has to stay behind and watch the orphans. She reveals to the orphans the truth (after being blackmailed by them into revealing what would happen to Annie right after accidentally revealing the secret.) They and Miss Hannigan are arrested by Franklin Delano Roosevelt's Secret Service.