The Bachelor (1999 film)

Bachelor Jimmie Shannon, after spoiling his proposal to Anne, his girlfriend of three years, discovers that his grandfather has died and left him the family business (worth $100 million) under the conditions that he be married by 6:05 p.m on his 30th birthday (the next day), that he not be apart from his bride for more than a week at a time over the next 10 years, and that they must attempt to produce a child sometime during the first five years of their marriage, leading the bachelor, his friends, and a priest to scramble over the next few hours in search of a bride.

If Jimmie fails, business competitor Oden Sports will buy the company and put Jimmy’s employees out of work. Meanwhile, Anne has second thoughts which she shares with her sister Natalie. She talks Anne into going home to go visit their parents for the night.

A desperate Jimmie opens a shoebox full of photos of old girlfriends, and begins to track them down. First he sees Stacey, an oil futures trader, who turns out to be engaged. Second is Zoe, a window dresser. Jimmie goes to see her, but just after, he runs off after a woman who he thinks is Anne. He returns to find Zoe has set a mannequin on fire.

He strikes out with an opera singer and a cop. Soon his list is depleted, but his last choice, Buckley, accepts: she detests Jimmie but wants his money to prop up her family's fortune. As the priest tries to conduct the ceremony, she gradually learns the other conditions of the will. Horrified, she drives away.

Anne misses Jimmie and heads back to the city. Trying to locate him, she calls Marco to arrange dinner with Jimmie.

As everyone scrambles to help Jimmie save the family business, Jimmie realizes the "effect" of marriage, as the priest reveals how he took on the priesthood after his wife died, and that he was proud to be married and produce a family in the process.

Realizing that he loves Anne and is ready to 'take the plunge', Jimmie, after being up all night, rests in the church where Marco had promised to deliver a bride. He awakens to find hundreds of women dressed as brides waiting for him. After trying to settle the women down, Marco lies and says it was all a prank. Marco reveals that Anne is on her way back, so Jimmie flees to the train station, ordering a cake on the way. He makes it there after escaping the brides. He finds Anne in the train, but she has discovered a newspaper with its front page asking, "Would you marry this man for $100 million?" with Jimmie's picture beside. She is upset, but he professes his love for her and they reconcile.

Natalie finds a discarded wedding dress in the station, and Anne puts it on in the bathroom. She opens the door to see hundreds of brides run past, chasing Jimmie. Jimmie flees. He eventually climbs up a flight on a fire escape and shouts for Anne, as the brides gather below. The priest begins to conduct the ceremony over a loudspeaker from inside a police car, causing many 'brides' to attack the car. Anne, in the crowd, makes her way through and up to Jimmie. Anne convinces the other women to be happy and let it be her day.

The priest finishes the ceremony by pronouncing them husband and wife, to cheers from all, and Jimmie and Anne kiss. They made it just in time before the deadline of 6:05 p.m. to inherit $100 million. She then tosses her bouquet into the teeming crowd below.

• Chris O'Donnell - Jimmie Shannon
• Renée Zellweger - Anne Arden
• Hal Holbrook - Roy O'Dell
• James Cromwell - The Priest
• Artie Lange - Marco
• Edward Asner - Sid Gluckman
• Marley Shelton - Natalie Arden
• Peter Ustinov - Grandad James Shannon
• Sarah Silverman - Carolyn
• Stacy Edwards - Zoe
• Rebecca Cross - Stacey
• Jennifer Esposito - Daphne
• Katharine Towne - Monique
• Mariah Carey - Ilana
• Brooke Shields - Buckley Hale-Windsor
• Anastasia Horne - Peppy Boor
• Pat Finn - Bolt

• The Bachelor at IMDb
• The Bachelor at the TCM Movie Database
• The Bachelor at AllMovie
• The Bachelor at Rotten Tomatoes
• The Bachelor at Box Office Mojo