The Wedding Planner made rom-com stars out of Jennifer Lopez and Matthew McConaughey

By 2000, Jennifer Lopez and Matthew McConaughey both wanted a change. She’d burst onto the scene with Selena, found critical acclaim in Out Of Sight, and settled into action/sci-fi fare like Anaconda and The Cell. He’d transitioned his memorable debut in Dazed & Confused into dramas like A Time To Kill and U-571, and was fresh off Ron Howard’s satirical flop EDtv. Lopez and McConaughey each thought a nice, light romantic comedy would make for a welcome change of pace. Little did they know that signing onto The Wedding Planner would define the course of their respective careers for the next decade.

If Hugh Grant, Meg Ryan, and Julia Roberts ruled the rom-com genre at the height of its 1990s renaissance, Lopez and McConaughey took command of the ship just as it was headed toward choppier waters. Along with actors like Kate Hudson, Reese Witherspoon, and Katherine Heigl, Lopez and McConaughey defined what rom-coms looked liked in the aughts, as the creative highs of the ’90s curdled into something more crassly commercial. Thanks to films like Monster-In-Law and Failure To Launch, both actors were written off as punchlines until their respective career renaissances (him for projects like Magic Mike and True Detective, her for Hustlers) reminded us that, hey, they can actually act. But even in their worst rom-com offerings, it was always clear that Lopez and McConaughey had talent. The problem was, they seldom got material that let them fully show it off.

The inspiration for The Wedding Planner came from an ad for a wedding planning course, which caught the eye of writing duo Michael Ellis and Pamela Falk. They met with real-life wedding planners for research, and became fascinated by a world where fairy tale romance meets logistical precision. In their film, elite wedding planner Mary Fiore (Lopez) is savvy at work but unlucky in love. (“Those who can’t wed, plan,” she jokes.) Then one day, a hunky pediatrician named Steve Edison (McConaughey) saves her life from a runaway dumpster. It seems like love at first neck brace until Mary discovers that—gasp!—Steve is engaged to her nouveau riche client Fran Donnelly (Bridgette Wilson-Sampras). Since Mary needs to land “the Donnelly account” to “make partner” at her, I don’t know, wedding planning firm, she attempts to recommit to the cardinal rule of her industry: “Don’t fall in love with the groom.”

In retrospect, it was perhaps foolish to tempt fate by including a literal runaway dumpster as a plot point. The critical skewering of The Wedding Planner was so severe that director Adam Shankman is still scarred by it today. (The film currently sits at a paltry 16% on Rotten Tomatoes.) Nevertheless, The Wedding Planner opened No. 1 at the box office, and made Lopez the first entertainer in the U.S. to have a No. 1 film and a No. 1 album—her sophomore record, J.Lo—simultaneously. The Wedding Planner eventually earned a solid $60.4 million domestically and burrowed deep into the rom-com canon as a regular cable staple. It’s even influenced the way people eat M&Ms, thanks to a scene where Steve suggests the brown ones have less artificial coloring. (Multiple deep-dives have proven it’s actually the opposite.)

It’s worth noting that the entire plot of The Wedding Planner wouldn’t exist if men were expected to wear engagement rings—not that sexist double standards are something the film is particularly interested in exploring. In fact, at just about every avenue where The Wedding Planner could become a thoughtful character piece about love and loyalty, it swerves toward the worst comedic impulses of first-time director Shankman. The dancer-turned-choreographer made a name for himself in Hollywood as a movement coordinator for films like Addams Family Values and Boogie Nights. He got attached to The Wedding Planner thanks to its producers: Jennifer Gibgot is his sister and Peter Abrams had worked with him on She’s All That, the teen rom-com where Shankman inexplicably turned a high school prom into a choreographed group dance.

The Wedding Planner features similarly inexplicable scenes, including a horse chase, a macho fitness contest, and an excruciating sequence where Mary and Steve frantically try to Krazy Glue a statue’s broken penis. As Roger Ebert put it, “When you have seen Jennifer Lopez ungluing marble genitals from the hand of the man she loves, you have more or less seen everything.”

I’ve previously argued that 2003’s How To Lose A Guy In 10 Days marks the turning point where the rom-com genre started to go downhill. But I actually think this earlier McConaughey vehicle is even more of an ur-text for the rom-coms of the aughts. The Wedding Planner prioritizes broad physical comedy over character-building in a way that would prove increasingly disastrous for the genre over the course of the decade. In addition to introducing Lopez and McConaughey to the romantic comedy sphere, The Wedding Planner also gave Judy Greer her first true rom-com best friend role, and helped further the career of Anne Fletcher, Shankman’s friend and assistant choreographer who would go on to direct popular romantic comedies like 27 Dresses and The Proposal. Shankman himself continued to helm rom-com-adjacent fare throughout the aughts, including A Walk To Remember, Bringing Down The House, and the 2007 Hairspray musical (his best film to date).

In The Wedding Planner, Shankman’s heightened sensibilities are put to good use in a heated tango class where Mary and Steve first hash out his ethical line bending. Shankman also opens the film with an impressive two-and-a-half minute continuous shot in which Mary weaves through a massive church wedding while displaying the precision of a CIA agent, the ingenuity of MacGyver, and the emotional dexterity of a therapist. There are a few places where The Wedding Planner effectively balances its exaggerated comedic tone with originality and characterization. On the whole, however, it struggles to find the right equilibrium.

The Wedding Planner is also plagued by massive logic issues, starting with the fact that it uncomfortably whitewashes Puerto Rican American Lopez into the daughter of two white Italian immigrants. In a bizarre subplot, Mary’s overprotective father (Alex Rocco) tries to pawn her off into a pseudo arranged marriage to her exuberant childhood acquaintance, Massimo (future Grey’s Anatomy star Justin Chambers, delivering one of the strangest “Italian” accents ever captured on film). Despite the fact that Mary doesn’t really like Massimo, she for some reason goes along with it when he crashes a wedding planning session claiming to be her fiancé, which leads to an off-putting scene where Steve berates Mary for her own duplicity during their flirtatious meet-cute.

McConaughey is at least able to soften Steve’s morally dubious behavior into something relatively palatable—an always important skill for a male lead in the rom-com genre. Given its uneven filmmaking, The Wedding Planner really lives or dies based on its central performances. McConaughey was brought onboard just four weeks before production began when original star Brendan Fraser had to drop out due to scheduling conflicts with Bedazzled. (Fraser had so enjoyed working with Shankman on George Of The Jungle that he named him his exclusive choreographer.) Though McConaughey’s role isn’t particularly showy, his laid-back confidence is an effective foil for Lopez’s star turn.

As in almost all of her rom-com work, Lopez has an ineffable appeal that makes you root for her no matter what over-the-top situations her character falls into. She manages to make Mary more than just a collection of type-A quirks, which is impressive given that there’s literally a scene where she vacuums her curtains. (It perhaps helps that Lopez could personally relate to Mary’s workaholism.) Though Lopez’s celebrity persona and music career hinge on glamour and power, as an actor she excels at making her characters feel real and relatable, even within a glossy rom-com context. In her best scene, Lopez turns in an all-time great drunk performance when Mary spirals after running into her ex-fiancé and his pregnant wife.

In the film’s production notes, Shankman lays out a compelling vision of how the four main characters each represent a different viewpoint on love. Mary is cynical, Steve is loyal, Fran is practical, and Massimo is completely openhearted. None of them are villains, they’ve just taken their respective worldviews too far, which has left them out of touch with what they really want from life. (It’s especially nice that The Wedding Planner doesn’t transform Fran into a “rich bitch” standing in Mary’s way.) To hear Shankman tell it, The Wedding Planner is about relatable human foibles and our inability to escape the ruts we get stuck in. The problem is, too little of that comes across in the film itself, which brushes past potentially interesting plot points—like the wounds Mary carries from getting dumped at the altar—to squeeze in more physical comedy hijinks.

In a way, though, it’s almost easier to appreciate Lopez’s and McConaughey’s skills as actors when they’re working with bad rather than good material. The Wedding Planner proved they could keep a rom-com ship afloat, even as it threatened to veer off course. And while Maid In Manhattan and How To Lose A Guy In 10 Days are the better films in Lopez’s and McConaughey’s respective rom-com oeuvres, we wouldn’t have them without The Wedding Planner as a launching point. As the rom-com genre headed toward its darkest days, it at least buoyed the careers of two of our brightest stars.

Next time: We’re totally buggin’ as Clueless turns 25.