Jessie Montgomery, portrayed by Ally Sheedy (St. Elmo’s Fire), is a wealthy, young adult, whose only goal in life, seemingly, is to spend her father’s money while partying. Charles, played by Emmy winner Tom Skerritt (Picket Fences), is distraught with Jessie’s lack of direction and her self-entitled attitude. After spending an enormous amount of money at a nightclub, the previous evening, the next night, when Jessie asks Charles for money, he refuses. Jessie, never one to miss the chance to go out, asks to borrow $50 from Mr. Montgomery’s driver, Woodrow (Teddy Wilson), knowing full well, that once her father finds out, he will pay Woodrow back.
Disgusted by her behavior, Charles looks up at the stars and says aloud that he wished he never had a daughter, which is the catalyst for the remainder of the film. The next day, neither her father, nor the members of the household staff remember her. After security is called, she reluctantly leaves. No matter where Jessie goes, no one, who she knew prior to her father making his wish, remembers her.
Wandering the streets, hungry and without money, she has no clue as to how to even attempt to get herself back on her feet. Stella Winston, a role acted by Emmy and Golden Globe nominee Beverly D’Angelo (Coal Miner’s Daughter), appears to her. As it turns out, Stella is Jessie’s fairy god mother. Stella lets Jessie know, that if she ever wants things to go back to the way they were, she has to prove herself. The first step, is for Jessie to get a job.
Jessie gets a job from an employment agency as a maid. She is assigned to work for rock ‘n’ roll promoter Stan Starkey (Dick Shawn) and his wife Georgette. The role of Mrs. Starkey is played by BAFTA winner Valerie Perrine (Lenny). As Jessie begins to work, she realizes that money is not merely given to someone, but earned. Along the way she makes friends with other members of the staff, whose problems don’t revolve around what party or latest hot spot they’re going to go to for the evening. One of the staff members who befriends Jessie is Audrey. The character is played by gospel singer and Grammy winner Merry Clayton (Twenty Feet from Stardom). (As an aside: Clayton, who sings a song during the film, did back-up vocals for a number of famous artists during the 1960s and 1970s. Clayton is perhaps most famous for singing a duet with Mick Jagger on The Rolling Stones song Gimme Shelter).
“Maid to Order” was directed by Amy Holden James (The Resident). James co-wrote the screenplay with Perry and Randy Howze (Chances Are). The film premiered in Beverly Hills on July 17, 1987. Parts comedy and fantasy, the movie has a runtime of 93 minutes.
The film was good, but, in my opinion, not as good as it could’ve been. I’ve always liked Ally Sheedy as an actress, and she did her best with what she was given to work with. The script, however, was a bit bland in parts and that brought down the overall film. I still enjoyed it, and if you like stories that play up the Cinderella theme, albeit this time instead of going from rags to riches, going from riches to rags and perhaps back again, you might enjoy this, at least for one time viewing.