Before he was the brooding Dr. Alex Karev, Justin Chambers was just a guy trying to make us believe he was an eccentric Italian named Massimo. If you grew up in the early 2000s, you probably remember the 2001 romantic comedy The Wedding Planner. It was the height of Jennifer Lopez's rom-com era. Matthew McConaughey was still in his "golden boy" phase. And then there was Justin Chambers. He played Massimo Lenzetti, the childhood friend of J.Lo's Mary Fiore. Honestly, it is one of the most polarizing and bizarre performances in modern rom-com history.
Some people love it. Others find it absolutely cringeworthy.
Watching Justin Chambers in The Wedding Planner now is a total trip, especially if you’ve spent fifteen seasons watching him roam the halls of Grey Sloan Memorial. He’s unrecognizable. He has a thick, cartoonish Italian accent. He carries around a Scrabble board. He wears sweaters that look like they were stolen from a high-end thrift store in Milan. It is a far cry from the "Evil Spawn" we came to know later.
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The Massimo Problem: Why the Role is So Divisive
Let’s be real for a second. The character of Massimo isn't exactly "subtle." In the film, Mary’s father (Alex Rocco) basically tries to arrange a marriage between Mary and Massimo. Massimo is enthusiastic. Like, very enthusiastic. He spends the movie chasing Mary around, professing his love in a way that feels more like a golden retriever than a romantic lead.
The accent is the big thing.
Justin Chambers is from Ohio. Springfield, to be exact. When he shows up on screen in The Wedding Planner, he is leaning so hard into the "Italian immigrant" trope that it almost feels like he's in a different movie than everyone else. While Jennifer Lopez and Matthew McConaughey are playing a standard, grounded rom-com, Chambers is playing a character who feels like he escaped from a Broadway musical.
But here’s the thing: it kind of works?
Massimo is the only character who is actually honest about what he wants. He’s sweet. He’s devoted. He builds a dollhouse for Mary’s dolls. He says things like, "I am a center for the physical fitness!" It’s ridiculous, but Chambers plays it with such genuine heart that you can’t help but feel a little bad for the guy when Mary inevitably chooses the pediatrician who almost died because of a runaway dumpster.
From Calvin Klein to Massimo
It is easy to forget that Justin Chambers was a world-class model before he was an actor. He was the face of Calvin Klein. He did campaigns for Armani and Dolce & Gabbana. When he was cast as Massimo, he was still relatively new to the Hollywood scene. He had a role in Liberty Heights in 1999, but The Wedding Planner was his first major brush with a blockbuster audience.
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The contrast between his real-life "cool guy" model persona and the dorkiness of Massimo is staggering. It shows a level of range that many didn't give him credit for at the time. He wasn't afraid to look silly. He wasn't afraid to be the guy you didn't want the girl to end up with.
The Grey's Anatomy Connection
Most fans rediscover Justin Chambers in The Wedding Planner through Grey's Anatomy. It’s a rite of passage for every Grey’s fan. You’re binge-watching Season 2, you see Alex Karev being a jerk, and you think, "Where have I seen this guy before?" Then you fire up Netflix or Prime Video, and there he is. Wearing a vest. Talking about "the bonding."
The "Massimo-to-Karev" pipeline is fascinating because it’s a complete 180. Alex Karev is defined by his defensive walls, his anger, and his struggle to be a "good man." Massimo is a man who has no walls. He is all heart, all the time.
What Most People Get Wrong About the Ending
There is a common misconception that Massimo is the "villain" of the movie. He isn't. He’s just the "wrong" guy. In the logic of 2000s rom-coms, the childhood friend is almost always a placeholder. But if you look at the facts of the film, Massimo is arguably a better partner than Steve (McConaughey). Steve is engaged to someone else (Fran) and spends the whole movie lying to Mary about it. Massimo is just... there. Waiting. Building dollhouses.
When Mary eventually leaves Massimo at the town hall to go find Steve, it’s supposed to be this triumphant moment. But re-watching it in 2026? It feels a little mean! Massimo takes it with such grace, though. He’s happy if she’s happy.
Why We Still Care in 2026
Justin Chambers has kept a fairly low profile since leaving Grey's Anatomy in 2020. He did a stint as Marlon Brando in The Offer (the miniseries about the making of The Godfather), which was another role where he transformed his voice and look. He’s clearly an actor who likes to disappear into a part.
The Wedding Planner remains a staple of the genre because of its cast. You have:
- Jennifer Lopez at her peak.
- Matthew McConaughey before the "McConaissance."
- Judy Greer being the best friend (as she always is).
- And Justin Chambers providing the weird, sweet comic relief.
If you haven't seen it in a while, it’s worth a re-watch just to see Chambers' performance. It’s a time capsule of a specific moment in Hollywood when we weren't afraid of a little camp.
Actionable Insights for Rom-Com Fans
If you're going down the Justin Chambers rabbit hole, don't just stop at The Wedding Planner. Check out his work in The Musketeer from the same year. It’s a very different vibe—lots of sword fighting and early-2000s wire work.
If you're watching The Wedding Planner for the first time, pay attention to the Scrabble scene. It’s the most "Massimo" moment in the film. It highlights exactly why Chambers was such a standout. He took a role that could have been a footnote and made it something people are still debating twenty-five years later.
Whether you find the accent charming or offensive, you can't deny that the guy committed to the bit. And in a genre that can often feel formulaic, that kind of commitment is actually pretty refreshing.
Next time you’re scrolling through streaming options, give Massimo another chance. He just wanted to be "body friends," after all.
To get the full Justin Chambers experience, watch The Wedding Planner back-to-back with the first three episodes of Grey's Anatomy. The whiplash is the best part. It’s the ultimate testament to his career—going from the man who built a dollhouse to the man who became one of TV's most beloved (and complicated) doctors.
Focus on the character's sincerity rather than the accent. It makes the movie a much more interesting watch. Massimo Lenzetti might not have won the girl, but he definitely won a weird, permanent spot in pop culture history.