Honestly, it’s hard to remember a time when Hugh Grant wasn’t the internet’s favorite "grumpy old man" who gives hilarious, blunt interviews. But back in 1999, he was still very much in his "bumbling Englishman" era. He had just come off the massive success of Notting Hill, and then he dropped Mickey Blue Eyes.
It’s a weird one.
The movie is basically what happens when you take a Richard Curtis-style protagonist and drop him into an episode of The Sopranos. In fact, a bunch of the guys in the cast literally ended up in The Sopranos. It’s a fish-out-of-water story that feels like a fever dream where Sotheby’s art auctions meet organized crime.
What is Mickey Blue Eyes actually about?
The plot is fairly straightforward, or at least it starts that way. Hugh Grant plays Michael Felgate, a dapper art auctioneer in Manhattan. He’s the kind of guy who says "gosh" and wears perfectly tailored suits. He falls head over heels for Gina Vitale, played by Jeanne Tripplehorn, a schoolteacher who seems perfect except for one tiny, terrifying detail.
Her dad is Frank Vitale. And Frank is played by James Caan.
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If you’ve seen The Godfather, you know James Caan as Sonny Corleone. Here, he’s playing a sort of "Sonny if he survived and opened a restaurant" version of a mobster. When Michael proposes, Gina panics. She’s not rejecting him; she’s protecting him. She knows that once you’re "in" with her family, you’re in forever.
Michael, being the optimistic Brit he is, thinks he can handle it. He tells her, "I'm marrying you, not your family." Famous last words. Within about twenty minutes of screen time, he’s unwittingly laundering money through his auction house and standing over a dead body.
The "Mickey Blue Eyes" Persona
The title comes from a desperate moment where Michael has to pretend to be a notorious hitman to save his skin. He adopts the name "Kansas City Little Big Mickey Blue Eyes." It is every bit as ridiculous as it sounds.
There’s a legendary scene where James Caan tries to teach Hugh Grant how to say "Fuggedaboutit."
It’s painful. It’s awkward. It’s also probably the funniest thing in the movie. Grant’s attempt at a New York mob accent sounds like a person having a mild neurological event. He squawks. He gurgles. He fails miserably. But that’s the charm. The movie knows he’s a "wimp" (Caan’s character’s words, not mine) and leans into it.
The Production Drama You Didn't Know About
Most people don't realize this was a Simian Films production. That was the company run by Hugh Grant and his then-girlfriend Elizabeth Hurley.
They were under a lot of pressure. Their previous film, Extreme Measures, hadn't exactly set the world on fire. According to interviews Grant gave at the time, the script for Mickey Blue Eyes was originally about a neurotic Jewish lawyer. They decided to change the lead to a Brit because the "Brit-meets-mob" dynamic felt fresher.
It wasn't a smooth shoot.
- Weather Problems: Winter weather actually damaged some of the footage during filming.
- Director Swap: The director, Kelly Makin, had to step away for a few days because his wife was having a baby. Carl Gottlieb, who wrote Jaws and The Jerk, actually stepped in to help with reshoots.
- The Mob Connection: To get the vibe right, Grant and Hurley actually hung out with real-life mobsters in New York. Apparently, the guys "worshipped" Elizabeth Hurley but thought Hugh was exactly the "English wimp" he plays in the movie.
Why the Critics Were Split
When it hit theaters on August 20, 1999, the reviews were... mixed. It holds about a 45% on Rotten Tomatoes.
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Roger Ebert wasn't a fan. He felt Hugh Grant was miscast and that the movie derailed when it tried to do the "fake mobster" bit. He thought Grant’s performance was too detached, like he was a "dinner guest" in his own movie.
On the other hand, some people loved the satire. It was poking fun at the very genre James Caan helped define. It also had to compete with Analyze This, which had come out earlier that year and dealt with similar "mobster-in-therapy" themes.
The box office reflected that struggle. It cost about $36 million to make (though some sources cite higher figures due to marketing) and brought in roughly $54 million worldwide. It wasn't a disaster, but it wasn't Notting Hill money.
The Sopranos Connection
If you watch the movie today, it’s a "Who’s Who" of prestige TV. You’ll spot:
- Vincent Pastore (Big Pussy from The Sopranos)
- Tony Darrow (Larry Barese)
- John Ventimiglia (Artie Bucco)
- Burt Young (Uncle Pat, and of course, Paulie from Rocky)
Is it worth a rewatch in 2026?
Honestly? Yeah.
It’s a relic of a time when studios weren’t afraid to make mid-budget romantic comedies that were actually kind of weird. The subplot involving "bad art" is actually genius. The mob boss’s son paints these horrific, gory pictures—like Jesus with a machine gun—and Michael is forced to auction them off for thousands of dollars to launder money.
It’s a cynical, funny look at the art world that still feels relevant.
If you’re looking for a masterpiece, this isn't it. But if you want to see James Caan being a legend and Hugh Grant making a complete fool of himself while trying to navigate the Lucchese crime family, it’s a solid Friday night pick.
How to Watch and What to Look For
If you're planning to revisit this 90s gem, keep an eye out for these specific things to get the most out of the experience:
- The "Bum Massage" Scene: There’s a scene where Michael’s boss walks in on him in a very compromising position. Grant later admitted they almost cut it because they thought it might make people "vomit," but it ended up being the biggest laugh in test screenings.
- The Soundtrack: It’s full of classic Italian-American crooner tracks that lean heavily into the stereotype, but they’re used with a wink and a nod.
- The Ending: No spoilers, but the wedding sequence is a masterclass in "farce" filmmaking—everything that can go wrong does, involving the FBI, fake shootings, and a lot of confused gangsters.
Next Steps for Fans:
Check out the 1999 interview with Hugh Grant on SPLICEDwire or One Guy's Opinion for some truly self-deprecating gold about how he felt he was "crap" in the original table reads. If you've already seen it, pair it with The Freshman (1990) for a double feature of "James Caan Parodying Himself."