5 Shocking Ways Matt Dillon's Pat Healy Redefined Sleaze In 'Something About Mary' 25 Years Later

The enduring legacy of Matt Dillon's performance as the manipulative, two-faced private investigator Pat Healy in the 1998 smash-hit romantic comedy *There's Something About Mary* remains a cornerstone of '90s cinema. Even today, a quarter-century after its release, Dillon’s pitch-perfect portrayal of the sleazy PI—who is hired to find Mary Jensen (Cameron Diaz) but becomes obsessed with her—is cited as one of the greatest comedic villain turns in film history, a role that completely subverted his earlier status as a brooding '80s heartthrob. The film, directed by the Farrelly Brothers, continues to be celebrated for its blend of sweetness and shocking gross-out humor, with Dillon's character providing the crucial, cynical anchor for the outrageous plot. The movie's recent 25th-anniversary retrospective in December 2025 has brought renewed attention to the incredible behind-the-scenes stories and the career-defining risks Dillon took in playing the colossal sleazebag Pat Healy. This deep dive explores how Dillon transformed from a dramatic actor in films like *The Outsiders* and *Drugstore Cowboy* into the unforgettable comedic menace who lied, cheated, and stalked his way into Mary's life.

Matt Dillon: A Detailed Biography and Profile

Matthew Raymond Dillon’s career spans over four decades, transitioning from a ‘Brat Pack’ icon to a respected dramatic and comedic actor, director, and producer. His role as Pat Healy proved his versatility and willingness to embrace a truly unlikable character for the sake of comedy.

• Full Name: Matthew Raymond Dillon
• Date of Birth: February 18, 1964
• Place of Birth: New Rochelle, New York, U.S.
• Parents: Mary Ellen Dillon (Homemaker) and Paul Dillon (Portrait Painter)
• Nationality: American
• Occupation: Actor, Director, Writer, Producer
• Breakthrough Role: Randy in *Over the Edge* (1979)
• Key Early Films: *The Outsiders* (1983), *Rumble Fish* (1983), *Drugstore Cowboy* (1989)
• Major Accolades: Academy Award Nomination (Best Supporting Actor) and Golden Globe Nomination for *Crash* (2004)
• Directorial Debut: *City of Ghosts* (2002)
• Notable Later Films: *Wild Things* (1998), *The House That Jack Built* (2018), *Capone* (2020)

The Audacity of Pat Healy: How Dillon Mastered the Sleazebag Role

Pat Healy is not just a villain; he is a masterclass in comedic deception, a character whose smarmy charm barely masks a deep-seated desperation and sociopathic tendency. Dillon’s casting was a brilliant stroke of counter-intuitive genius by the Farrelly Brothers, who saw past his dramatic roots.

Dillon had to play the role completely straight, which is what makes the comedy land so hard. His character's actions—from fabricating a career as a "career criminal" and suspected serial killer to falsely claiming he works with "retards" to gain Mary's sympathy—are genuinely dark, but delivered with such conviction that they become hilariously absurd in the context of the film's over-the-top tone.

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1. The Shocking Real-Life Romance with His Co-Star

Perhaps the most mind-boggling piece of trivia from the set is that Matt Dillon and Cameron Diaz (Mary Jensen) were actually dating in real life during the filming of *There's Something About Mary*. This fact adds an entirely new layer of complexity to their on-screen dynamic. While Pat Healy is relentlessly stalking and lying to Mary, the actors themselves were in a relationship, which reportedly lasted from 1995 to 1998, ending shortly after the film's release.

This behind-the-scenes context makes the scenes where Pat Healy is intensely spying on Mary, using a directional microphone and binoculars, feel even more surreal. The tension and chemistry between them, even when he's being a total creep, is palpable, likely fueled by their real-world connection.

2. He Was Not the Farrelly Brothers' Original Choice

The role of Pat Healy almost went to a completely different comedic legend. According to behind-the-scenes stories, the Farrelly Brothers’ first choice for the role was none other than Bill Murray. Murray had just worked with the directors on their previous film, *Kingpin* (1996). However, the role ultimately went to Dillon, a veteran of serious dramas, marking a significant pivot in his career.

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Dillon’s dramatic background is precisely what made his performance so effective. He didn't play Pat Healy as a cartoon; he played him as a genuine, manipulative creep, which made the comedic elements—like the infamous scene with the dog Puffy—all the more jarring and funny. He brought a grounded intensity that a purely comedic actor might have missed.

3. The Iconic "Dog Puffy" Scene Was a Game-Changer

One of the film’s most memorable and controversial sequences involves Pat Healy and Mary’s dog, Puffy. After Healy is attacked by the dog, he attempts to dispose of it, resulting in a series of escalating, absurdly violent events. This scene, along with the "hair gel" sequence, cemented the film's reputation as a groundbreaking "gross-out" comedy that pushed the boundaries of what was acceptable in a mainstream romantic comedy.

Dillon’s straight-faced reaction to the escalating chaos—including the dog being accidentally electrocuted and then fitted with a full-body cast—is what sells the humor. He plays the villain who is utterly unfazed by the moral implications of his actions, only concerned with covering his tracks and maintaining his facade for Mary.

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4. The Role Resurrected His Career in a New Genre

Prior to *Something About Mary*, Matt Dillon was primarily known for intense, dramatic roles in films like *To Die For* and *Singles*. While respected, his career needed a jolt. Pat Healy provided that shock.

The film was a massive commercial success, earning over $369 million worldwide, and proved that Dillon could excel in comedy. This performance opened doors to other major roles, including his critically acclaimed, Oscar-nominated performance as Officer Ryan in Paul Haggis's 2004 drama *Crash*, demonstrating a renewed career versatility that continues to this day. The Pat Healy role allowed the industry to see him as more than just a dramatic leading man.

5. The Pat Healy Character is a Crucial Topical Entity

The character of Pat Healy, alongside Ted Stroehmann (Ben Stiller), Mary Jensen (Cameron Diaz), and Tucker/Dom 'Woogie' Wogan (Lee Evans), is a vital entity in the film's narrative structure and cultural impact. Healy represents the dark side of romantic obsession, a theme that the Farrelly Brothers explore through escalating absurdity.

The film is a case study in situational comedy and character-driven farce. Healy's elaborate lies—including pretending to be a successful architect and a world traveler—are constantly being exposed by the other men obsessed with Mary. This web of deceit creates the narrative engine of the entire film. The character is so iconic that he is frequently listed among the greatest comedic villains of all time, a testament to Dillon's commitment to the role.

The Lasting Cultural Footprint of Dillon’s Comedic Turn

Today, *There's Something About Mary* is considered a cult classic and a defining film of the 1990s comedy genre. The movie’s enduring topical authority is undeniable, with its jokes and scenes frequently referenced in pop culture.

Matt Dillon's willingness to shed his 'Brat Pack' image and fully embrace the unredeemable sleaze of Pat Healy is what makes the performance so memorable. He didn't seek sympathy; he sought to be repulsive, and in doing so, he delivered a comedic masterpiece. The film’s 25th anniversary serves as a powerful reminder of how one audacious performance can fundamentally change a respected actor's career trajectory, proving that there is always something about a truly great comedic performance that stays with the audience.

Key Entities and LSI Keywords

• Farrelly Brothers (Peter and Bobby)
• Cameron Diaz (Mary Jensen)
• Ben Stiller (Ted Stroehmann)
• Lee Evans (Tucker/Dom Wogan)
• Chris Elliott (Dom 'Woogie' Wogan)
• Private Investigator
• Romantic Comedy
• 1998 Film
• 25th Anniversary
• Gross-out Humor
• Cult Classic
• Bill Murray
• *Kingpin* (1996)
• *The Outsiders* (1983)
• *Drugstore Cowboy* (1989)
• Officer Ryan in *Crash* (2004)
• *Wild Things* (1998)
• Pat Healy's Dog Puffy
• Career Criminal
• The "Hair Gel" Scene
• Miami, Florida Setting
• Ted's Zipper Incident