Fun Crime Movies I (Kinda) Forgot About

As 2023 wrapped up, I had this sinking feeling I hadn't watched many crime movies lately. It was late December. A guy likes to tally up the year. I did better than feared, though the count was heavily weighted to traditional rewatches like The Maltese Falcon and Clue. 

FOMO set in, and I started Googling around for recent crime movies. As will happen, I fell into internet rabbit holes and wound up checking out films from years past. Movie after movie elbowed back into my short attention span. Here with rewatch and supplemental research are five from back yonder that pretty much slipped my mind.

Disclaimer: My filter was crime comedies over a decade old and that slipped my mind, not what's up there with The Sting. These are varying shades of good fun, though, and all worth a first or second watch.

In Bruges (2008)

This artful, darker-than-dark comedy earned its share of attention.Colin Farrell won most of that attention as the hitman main character hiding in Bruges and haunted by accidentally killing a kid. This was Farrell's turn toward Serious Acting, and fate brought him writer/director Martin McDonagh and a role worth treading the boards. Still, Ralph Fiennes is gold in everything he does. He was a perfect choice for M, he was magnificent in The Grand Budapest Hotel (one hell of a crime movie), and he was the best character here, a crime boss unshakably convinced that violence should stay among criminals. The comedy is there but so bleak that sometimes it hits as drama. This is a complex film, powerful and aware of itself, but worth taking in if you're ready for a challenge. Bonus watch joy if you've been to Bruges. I've climbed that tower--twice.

Grosse Point Blank (1997)

Continuing on with hitman comedies...

Grosse Point Blank has a hitman going to his ten-year high school reunion. Jon Cusack stars in what, at first glance, feels like a vehicle outside his wheelhouse. "Ex-CIA assassin-turned-sociopath-freelance" isn't Cusack's, but suddenly he's doing it just fine. There's a sometimes-darkness to his acting that he calls on here for comic impact. In a movie about remembrances, this one is better than you might remember. Minnie Driver nails it as the girl he stood up at senior prom. Now, a failed marriage later she's a DJ querying her indie audience and reunion arrivals about whether he's worth another try. Her father, it turns out, is Cusack's contract. It's a concept comedy but with genuine wit and something to offer.  

Midnight Run (1988)

Okay, this one I had forgotten about. My bad, because it's a buddy comedy done well. Yes, Midnight Run leans into genre. There are mobsters, there's a dirty accountant, there's extended train action, but there's also real feeling and real chemistry. Robert De Niro, having made his bones at dramatic powerhouse, wanted to try his hand at comedy. Big was the movie he angled for, but Midnight Run is what he landed. The idea was to pair him with Bruce Willis or Robin Williams, but Charles Grodin was the choice after his acting sparks with De Niro at audition. A hard choice, apparently. Paramount backed out of the movie over Grodin's casting. Their mistake. Light comedy is Grodin's thing, but I can't think another film that gave him this much deeper to do. The result is chemistry indeed and a relentlessly entertaining ride. 

Heartbreakers (2001)

Con movies have a special place in my heart. The longer or deeper the con, the better. Con stories are psychological studies, and while Heartbreakers is too broad a comedy to explore the psyche in depth, an old soul works beneath the caper shenanigans. Sigourney Weaver and Jennifer Love Hewitt are a mom-daughter team fleecing would-be husbands of mini-wealth. It's time for Palm Beach and a whale, Gene Hackman's chain-smoking Big Tobacco CEO, and the con refuses to lay straight. Part of the problem is Ray Liotta as a past mark who can't let things go. Boil away the easy jokes and the period Florida excess, and what's left is prospective lovers jousting in the marriage game toward an all's-well ending. Shakespeare? No. Funny and at times charming? Yes. It's light fun when light fun can be healing. Shakespeare made a few of these comedies, you know.

Intolerable Cruelty (2003)

I'm a major admirer of the Coen brothers. I've watched the hell out of The Big Lebowski, and maybe that's not even their best crime comedy. True Grit might be, if you call it a comedy. Or Fargo is their best, or O Brother, Where Art Thou, or I could keep going. Intolerable Cruelty never tops anyone's list. Mine, either. But Intolerable Cruelty is good conniving fun, with a tone unique for the Coens. The brothers didn't start out to make this movie. They were hired as script doctors after the project had bounced around Hollywood. It kept bouncing even then until it landed back with the Coens. George Clooney is his syllable-perfect as the divorce attorney extraordinaire engaged in a battle of wits with Catherine Zeta Jones' professional wife. The stakes rise comically out of control in a tale about love's travails and its rare moments of grace.