Honestly, it’s been nearly twenty years, and yet the moment that first letter arrives, most of us are still a total mess. It’s a rare thing. Usually, romantic dramas from the mid-2000s feel a bit dated or overly sugary when you revisit them, but the actors in the movie P.S. I Love You managed to ground a fairly fantastical premise in something that felt painfully, awkwardly real. It wasn’t just about the letters. It was about how people actually grieve—messy apartments, singing loudly to distract from the silence, and getting incredibly angry at people who are already gone.
Richard LaGravenese, who directed the 2007 film, had a massive task. He had to take Cecelia Ahern's best-selling novel and find a cast that could balance the crushing weight of widowhood with the lighthearted, almost slapstick humor required for the Ireland sequences.
The Hilary Swank Transformation
Before this film, Hilary Swank was the "serious" actress. She had two Oscars for Boys Don't Cry and Million Dollar Baby. People didn't really see her as a romantic lead. But as Holly Kennedy, she showed a vulnerability that was less about physical toughness and more about emotional fragility. She’s quirky. She’s neurotic. Seeing her belt out "Man! I Feel Like a Woman!" in a karaoke bar while wearing a ridiculous outfit is probably one of the most humanizing moments in 2000s cinema.
Swank’s performance is the anchor. If she didn't sell the devastation of losing Gerry, the rest of the movie would have felt like a gimmick. Instead, we see her go through the stages of grief in a way that isn't linear. One minute she’s fine, the next she’s smelling his old sweaters. It's relatable.
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Gerard Butler and the Ghost of Gerry
Then there’s Gerard Butler. At the time, he was coming off the hyper-masculine success of 300. Swapping a Spartan shield for a leather jacket and an Irish brogue was a huge shift. Now, let’s be real for a second: Butler’s Irish accent has been the subject of many jokes over the years. Even he has admitted it wasn't perfect. But does it matter? Not really.
The chemistry between him and Swank is what carries the film. He had to play a man who was dead for 90% of his screen time, appearing only in flashbacks or imagined sequences. He had to be charismatic enough that the audience understood why Holly couldn't let go, but not so perfect that he felt like a cardboard cutout. Gerry Kennedy was loud, a bit of a troublemaker, and deeply devoted. Butler brought a rugged warmth that made the letters feel earned.
The Supporting Cast That Stole the Show
You can't talk about the actors in the movie P.S. I Love You without mentioning the powerhouse supporting lineup. It’s actually kind of insane when you look back at who was in this.
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- Kathy Bates as Patricia: She plays Holly’s mother, and she provides the cynical, protective edge the movie needs. She isn't just the "supportive mom." She’s the woman who watched her husband leave and doesn't want her daughter to be destroyed by a different kind of loss. Her reveal at the end of the movie—which I won't spoil if you're a first-time viewer—is the emotional pivot point of the whole story.
- Lisa Kudrow and Gina Gershon: They play the best friends, Denise and Sharon. Kudrow is essentially doing a sharper, more husband-hungry version of her comedic persona, and it works perfectly to lighten the mood. The "husband checklist" scene is a classic for a reason.
- Jeffrey Dean Morgan: Before he was Negan or even fully established as John Winchester, he showed up as William, the rugged Irish musician. His entrance changed the energy of the film’s second half. He provided a bridge for Holly—a way to move forward without feeling like she was betraying Gerry.
- Harry Connick Jr.: He plays Daniel, the awkward, blunt, and slightly "on the spectrum" suitor who works at the family pub. His character is fascinating because he’s essentially the anti-Gerry. He’s safe. He’s honest to a fault. Connick Jr. plays the "friend zone" with a lot of dignity, even when his character is saying things that make you cringe.
Why the Casting Worked
The film succeeded because it didn't lean too hard into the "weepy" territory without giving us some grit. James Marsters (of Buffy fame) and Nellie McKay also rounded out a cast that felt like a real social circle. When you watch them all together, it feels like a group of people who have known each other for decades.
The locations helped, too. While not "actors" in the literal sense, the Wicklow Mountains and the streets of Manhattan functioned as characters. The contrast between the cramped, gray reality of New York and the lush, sweeping greens of the Irish countryside mirrored Holly's internal journey.
The Legacy of the Performances
Interestingly, the movie received mixed reviews from critics when it first dropped. Some found it manipulative. But the audience didn't care. It became a cult classic because of how the actors handled the concept of "continuing bonds." In psychology, we talk about how people don't "get over" grief, but rather learn to live with it. The actors in the movie P.S. I Love You portrayed that beautifully.
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They showed that moving on isn't about forgetting; it's about integration.
If you are looking to revisit the film or are diving into it for the first time, pay close attention to the non-verbal cues. Watch the way Kathy Bates looks at Holly when she thinks Holly isn't looking. Watch the subtle shift in Hilary Swank’s posture as the film progresses from winter to spring.
Next Steps for Fans and Viewers:
- Check out the Sequel: Cecelia Ahern actually wrote a follow-up novel titled Postscript in 2019. It picks up seven years after the original events and deals with a group of terminally ill people inspired by Holly’s story.
- Explore the Soundtrack: The music was a massive part of why the actors' performances landed so well. Re-listen to "Galway Girl" by Steve Earle and "Fairytale of New York" by The Pogues to capture that specific atmosphere.
- Visit the Filming Locations: If you’re ever in Ireland, Sally Gap and Whelan’s Pub in Dublin are must-visit spots for fans. You can actually stand in the places where Gerry and Holly "met."
- Watch the "Waking Up" Scene Again: Study the lighting and the lack of dialogue in the scene where Holly first realizes Gerry is truly gone. It remains one of the most effective depictions of immediate loss in modern cinema.