Remaking the Classics: The Bachelor (1999)

In 1925, Buster Keaton released Seven Chances — a film based on the play of the same name. Just over 70 years later, in 1999, a remake of Keaton’s brilliant marital comedy was released. The Bachelor takes the tale of a man who must marry within 24 hours to secure an inheritance and updates it to the modern day.

Jimmie Shannon (Chris O’Donnell) has gone on a lot of dates, but has never found the perfect gal for him… until he meets Anne (Renee Zellweger). The two hit it off the first time they meet, in a diner just after he has broken off a fling. Three years later, they’re still together.

When Anne catches the bouquet at a friend’s wedding, Jimmie feels pressured to propose, but he completely flubs his chance by saying “You win,” rather than anything romantic, sweet, or vulnerable. Anne rejects his offer, and rightfully so, taking an assignment in Athens to give herself some space.

When Jimmie’s grandfather dies, he learns that he is eligible for a $100 million inheritance… if he gets married by his 30th birthday, which is the next day! Naturally, he wants to fix his mistake with Anne and propose to her again, but will she accept? And if she doesn’t, will he be able to find a bride in time to get the dough and save the family business from sale?

The Bachelor was written by Steve Cohen, calling on both the original play and the 1925 screenplay. This remake was directed by Gary Sinyor.

The Bachelor was panned by most critics and bombed at the box office. But I have to say, for the most part, I enjoyed it! It’s a very distinctly turn-of-the-21st update on the story of Seven Chances, with some funny dialogue, a nice soundtrack, and even a Mariah Carey cameo. A metaphor with horses is used, recalling other films of the time, like 2001’s Someone Like You with its “new cow” theory. The grandfather’s will, rather than being a lengthy hand-written document, comes in the form of a very funny video message recorded before the man’s death.

Beyond the laughs I got from it and the appropriate updates to bring the familiar premise up to the modern day, there were a few other things I enjoyed about The Bachelor, namely the somewhat-expanded development of the female lead (known only as “His Girl” in the 1925 film; Anne in this 1999 version) and the time dedicated to building the relationship between Jimmie and Anne. I greatly enjoyed Anne’s relationship with her sister (portrayed by Marley Shelton), too.

Keaton’s character in Seven Chances was a man deeply in love but scared to share the depth of his feelings. O’Donnell’s Jimmie, on the other hand, is completely commitment-phobic, and even goes so far as to compare the bouquet toss to Shirley Jackson’s “The Lottery,” lending this remake a different angle. He comes to his senses by the end of the film, realizing that he truly loves Anne and has a good thing going with her, but in the interim he’s an utter fool.

A less forgettable actor could have been chosen for this lead role; I find O’Donnell and his performance quite bland. But I do think the critics were far too harsh on this film, many of them influenced by anti-remake snobbery. Yes, Keaton’s film is brilliant. He’s one of my favorite silent stars and I adored the 1925 film from the very first time I saw it. But, while obviously it isn’t as great as the original film, The Bachelor is still a decent watch that brings several laughs. The Keaton film is a must-see, but I would recommend this one, too, if you’re into late 1990s/early 2000s rom-coms.