The Bachelor

The setup is pure Hollywood gold, albeit slightly frantic: Jimmie Shannon (O'Donnell, fresh off his stint as Robin in the Batman franchise) is a charming guy who runs a traditional bespoke suit company with his best buddy Marco (Artie Lange, providing the requisite sarcastic sidekick commentary). Jimmie loves his girlfriend Anne (Zellweger, radiating that pre-Bridget Jones charm that made her a star), but commitment gives him hives. That all changes when his cantankerous grandfather (the legendary Hal Holbrook) kicks the bucket, leaving Jimmie a staggering $100 million inheritance... if he gets married by 6:05 PM on his 30th birthday. Which, naturally, is tomorrow.

Cue the panic. Jimmie's initial, disastrously clumsy proposal to Anne sends her running, leaving him with roughly 24 hours to find any willing bride. What follows is a whirlwind tour through Jimmie's little black book, facilitated by Marco and a bewildered priest (James Cromwell in a small but amusing role). This structure allows for a parade of cameos, essentially Jimmie cycling through past flames. Some are brief and funny (Sarah Silverman, Jennifer Esposito), others slightly more... memorable, shall we say? We get Brooke Shields as a demanding stockbroker and, in perhaps one of the film's most talked-about (and often criticised) moments, Mariah Carey as an opera singer named Ilana. Her appearance was part of her early foray into acting, and let's just say it certainly got people talking back in '99, though perhaps not always for the intended reasons.

Directed by Gary Sinyor, whose work might be less familiar to US audiences, The Bachelor absolutely feels like a 1999 rom-com. It’s got that slightly glossy but still grounded look, before digital grading smoothed everything over. San Francisco provides a genuinely lovely backdrop, captured with a straightforwardness that feels refreshingly real compared to the hyper-stylized cityscapes we often see today. There's an earnestness to it, even amidst the absurdity. O'Donnell plays the slightly overwhelmed everyman well enough, though the character's rapid shifts between panic and romantic pining can feel jarring. Zellweger, however, is effortlessly winning, giving Anne a warmth and intelligence that makes you root for her, even when Jimmie is acting like a complete doofus (which is often). You can already see the star power that would soon launch her into the stratosphere.

The film juggles its comedic premise with attempts at genuine romance, sometimes successfully, sometimes less so. The dialogue, penned by Steve Cohen, lands some decent laughs, particularly from Lange, but occasionally veers into sitcom territory. It cost around $21 million to make and pulled in just under $38 million worldwide – respectable, but hardly the blockbuster smash the premise might have suggested. Critics at the time were largely unkind (it still sits under 10% on Rotten Tomatoes), often pointing out the thin characters and the awkward blend of slapstick and sentimentality.

But let's be honest, the reason many people remember The Bachelor (if they remember it at all) is the climax. Echoing the Buster Keaton original, Jimmie's plight inadvertently gets published in the newspaper. The result? Hundreds upon hundreds of women in wedding dresses descending upon him, chasing him through the streets of San Francisco in pursuit of that $100 million. It’s a sequence of pure, escalating chaos. Forget intricate CGI – this is largely practical, showcasing hordes of extras in white gowns stampeding after our hapless hero.

Wasn't that sight something else back then? It’s utterly ridiculous, yet undeniably memorable. Watching it now, there's a certain charm to its sheer analog mayhem. It’s the kind of large-scale, slightly cumbersome comedic set piece that feels distinctly of its era. You can almost feel the logistics involved in wrangling that many wedding dresses! It’s a far cry from Keaton's legendary stunt work, of course, but as a modern interpretation, it delivers a uniquely chaotic payoff that justifies the entire setup, however silly.

The Bachelor isn't a hidden gem of romantic comedy, let's be clear. It's flawed, the central character can be frustrating, and some of the humour feels dated. Yet, finding this on a dusty VHS tape evokes a specific kind of late-90s nostalgia. It’s got appealing leads in O'Donnell and especially Zellweger, a killer high-concept premise borrowed from a silent film master, and that truly unforgettable bridal stampede. It was one of those ubiquitous rental store staples – maybe not your first choice, but you probably watched it on a rainy Saturday afternoon.

Justification: The rating reflects a film that's more memorable for its wild premise and chaotic climax than its overall execution. Zellweger's charm and the sheer novelty of the Keaton connection bump it up slightly, but weak characterization, uneven tone, and that underwhelming box office performance keep it firmly in the middle-of-the-road category. It's a pleasant enough distraction, but far from essential 90s viewing.

Final Thought: A prime example of late-90s studio rom-com machinery attempting something ambitious (by way of Buster Keaton!), ending up as a perfectly adequate, if slightly frantic, trip down the aisle of Blockbuster memories. You'll remember the brides, even if you forget why they were running.