James Caan's 15 best performances

Truth be told, when most people think of , they’re likely thinking about the television adaptation, which was based on this thought-provoking film. Set in 1991, it explores what happens three years after formerly enslaved aliens—dubbed “Newcomers”—arrive on Earth and began to assimilate into the everyday life of Los Angeles. A human cop, Sykes (Caan), and a Newcomer cop, Sam Francisco (Mandy Patinkin), partner up to solve the murder of a Newcomer. It’s a reluctant buddy drama with a sci-fi twist, with Caan breathing life into a maverick character who’s alternately racist, understanding, cranky, impatient, and friendly as he slowly grows to respect and then befriend Francisco.

runs 107 minutes, and Caan spends most of it confined to a bed, as his character, bestselling author Paul Sheldon, contends with unhinged fan Annie Wilkes (Kathy Bates). Bates won a Best Actress Oscar for her performance, and deservedly so, while Caan, who completes and complements her performance, didn’t even receive a Best Actor nomination. We get it, though. Bates has the flashier role, while Caan is called upon to simmer and stew and scheme, with occasional bursts of mostly verbal fury, and flashes of fake warmth. He pulls you in, even though Sheldon is a bit of a jerk. And just try not to scream in terror along with Sheldon when Annie takes a sledgehammer to his ankles.

Caan returns to comedy mode for . Here, he’s Tommy, a likeable Las Vegas gambler who meets a school teacher, Betsy (Sarah Jessica Parker) and her boyfriend, a private investigator named Jack (Nicolas Cage). Jack loves Betsy, but promised his mother he’d never get married. Anyway, Jack loses a load of money to Tommy, who agrees to let him off the hook in exchange for a weekend in Hawaii with Betsy. She starts to fall for Tommy, while Jack grows ever more desperate. Caan breezes through most of the movie looking stylish and oozing charm (especially in his scenes with the effervescent Parker) … until a character shift that Caan can’t sell because it just feels so wrong.

Owen Wilson, Luke Wilson, and Robert Musgrave star as friends with lofty dreams of becoming crooks in , Wes Anderson’s feature directorial debut. But like bottle rockets, they’re far, far from serious explosives. The trio connect with Mr. Henry (Caan), a more established criminal who sees the humor in everything and uses a semi-legit gardening business, Lawn Wranglers, as a front for his operations. Caan, at the time, was the only “name” in the movie, and he lends it gravitas. Mr. Henry is a hero to the boys, and Caan delivers the character’s humor, tough love, and affection in equal measure. If Caan ever gave a sweet performance, this is it.

Hot off his success writing The Usual Suspects, Christopher McQuarrie wrote and directed this convoluted and ultra-violent but engrossing thriller . Benicio del Toro and Ryan Phillippe play criminals who see a big payday in kidnapping a woman (Juliette Lewis) who’s carrying a baby for an older man (Scott Wilson) and his much younger trophy wife (Kristin Lehman). Hmmm, bad idea. The older man turns to an old friend, Joe (Caan), who takes matters into his own hands. It’s nothing Caan hasn’t played before, but, really, no one does it better. Here, he puts a fresh spin on it, as Joe is generally soft-spoken and more of a working-class guy and less nattily attired than most of Caan’s cons. Try not to get chills when Caan intones, “I handle Mr. Chidduck’s laundry, things like you. I make unpleasant decisions for him, which he can’t and never will know. And … he sleeps very well.”

The endlessly wonderful needed a Scrooge character to really put it over the top. Enter Caan as Walter Hobbs, a grumpy book publisher who is shocked to learn that Buddy (Will Ferrell), the lunatic man-child running around New York City in an elf costume, is his birth child. Caan somehow manages to keep a straight face while Ferrell brings the craziness. Actually, his face contorts in spasms of bewilderment and exasperation, until Buddy’s pure, unabashed joy wins him over. You just know that there’s a softie under that tough exterior, and when Walter finally gives in, Caan does it with a relatable slow burn that makes it that much more powerful. And, while the Ferrell-Caan scenes are pivotal, his moments with Mary Steenburgen as Walter’s wife Emily and young Daniel Tay as his son Michael set the stage for Walter’s turnaround. It’s as if they, like Buddy, see something in Walter that he might not even see in himself. And that emanates from Caan.

There’s more than a bit of Walter Hobbs in Caan’s Cloudy character, . Well, minus the meanness. Tim is the father of tinkerer and inventor extraordinaire Flint Lockwood (Bill Hader), who thinks big but tends to bungle things. Case in point, his latest contraption converts water into food, but it soon goes haywire and it starts raining hamburgers, strawberries, spaghetti, pancakes, and more. Can Flint save the day, get the girl (Anna Faris), and earn the respect and affection of his technophobic dad? Spoiler … of course, he can. And it’s fun to listen as Caan evolves the character, in just a handful of scenes, from doubting to proud. It’s more of the same in the sequel, though in the second go-round, Tim teams up to help his son—a transformation that Caan makes us believe for more reasons than the script says so.