The Raunchy Comedy With More Heart Than Anyone Expected

By the late ’90s, raunchy comedies were hardly new, but There’s Something About Mary landed with a jolt of energy that felt different. It wasn’t just the outrageous gags or gross-out set pieces, it was a film with surprising warmth that made its characters memorable beyond the punchlines. For the Farrelly brothers, whose Kingpin had flopped two years earlier, this wasn’t just another swing. It felt like a make-or-break moment, and they put everything into making it count.

The casting story itself is part of that legend. The Farrelly brothers wanted Ben Stiller for the lead from the start; the studio pushed back and urged them to find someone else. As a compromise, the brothers suggested an untested Owen Wilson, but the studio eventually relented and let them go with Stiller. That vote of confidence paid off, Stiller anchors the film with an affable awkwardness that lets the chaos around him land harder.

Stiller’s Ted is fine, steady, likable, and reactive, but this isn’t a role that needs star virtuosity. Instead, the movie belongs to the players who push the material further. Matt Dillon, as Pat Healy, is extraordinary: sleazy, reprehensible and utterly magnetic. Dillon commits to Healy’s nastiness so fully that every scene he dominates becomes a combustible, unforgettable mess.

Cameron Diaz, meanwhile, is the film’s conscience. As Mary, she brings a natural charisma and warmth that makes the entire love triangle (rectangle? pentagon?) believable. Diaz makes Mary feel like someone worth pining for, not trophies and punchlines, and she does it with a simplicity and charm that anchors the film’s heart.

Keith David turns a brief appearance into a highlight. His improvised beats during the pre-prom sequence are perfect comic detonations, a steady of straight-faced brilliance that elevates a scene already buzzing with tension. Small moments like his remind you how much the film gets right in terms of casting and tone.

What separates There’s Something About Mary from many of its raunchy contemporaries is storytelling discipline. The Farrelly brothers and their co-writers structure the film around a surprisingly solid romantic throughline. Even as the script embraces gross-out humor, it never forgets who the characters are or why their dents and flaws matter. Crucially, the jokes are aimed at grotesque behavior rather than punching down, a difference that helps the film age better than many of its peers.

There’s also the backstory: after Kingpin underperformed, the Farrellys believed their mainstream window might be closing. That pressure sharpened the movie. You can feel it in the assassination-level precision of the gags, in the economy of the script, and in the way the film manages to be both shocking and oddly tender in equal measure.

Still, the film isn’t flawless. A few set pieces rely on shock value more than craft, and the comic escalation occasionally tips into cartoonish excess. But even those moments are tempered by the film’s underlying warmth; the laughter is usually directed at outrageous behavior rather than at a scapegoated character.

At its best, There’s Something About Mary is a rare kind of studio comedy: one that can be filthy and humane at the same time. It gave Stiller a career-defining lead, launched Diaz into superstardom and proved the Farrelly brothers could combine heart and gross-out with surgical efficiency. Two decades on, it still earns laughs, and, more importantly, it still has a surprising amount of heart.