Here are the best James Caan films you’ve never seen

He went to the mattresses.

Years before James Caan’s star turn as Sonny Corleone in “The Godfather” (1972), the actor was hard at work in the Hollywood trenches, throwing himself into roles both large and small in hopes of hitting the big time.

Every fan of the late actor, who died Thursday at 82, knows the Bronx-born legend as Axel Freed in “The Gambler” (1974), or the unlucky author in “Misery” (1990). But, you won’t find those widely-celebrated films on this list of underrated (and sometimes downright obscure or strange) Caan movies, starting all the way at the tail end of the black and white era.

Whether the film is really good or just plain odd, Caan is always a pleasure to watch.

Nobody was ready for this twisted thriller pairing Caan (playing a brutish, Brando-esque jerk) with screen legend Olivia de Havilland. Columnist Hedda Hopper called for the film to be burned. The sort of movie that most likely did well on 42nd Street, and almost nowhere else, it offers a punch-in-the-face look at a transitional moment in American culture.

Howard Hawks’ sort-of-remake of “Rio Bravo” was the first time Caan, playing a young gun out for vengeance, really got noticed — it didn’t hurt to have John Wayne as a co-star. Critics showed up for this one.

This “what the hell did I just watch” film stars Caan and Katharine Ross as a bored, immature Manhattan couple that invite a German cosmetics salesperson (Simone Signoret) into their home, only to mess with her mind for sport. Roger Ebert’s review of the film referred to Caan as “one of the rare young male actors of ability in Hollywood today.”

Caan first collaborated with Francis Ford Coppola on this lovable, forgotten road trip movie, giving it his all as a football player suffering from brain damage who links up with a bored New York hausfrau (Shirley Knight). Critics didn’t totally get it, but they couldn’t ignore Caan’s acting chops.  

Playing the peaked-in-high-school Harry ‘Rabbit’ Engstrom in an ill-fated adaptation of John Updike’s novel, Caan managed to make the few people that saw the film hate him. He played the irresponsible dad that goes out for cigarettes and doesn’t come home. Years later, Caan recounted his excitement for the project; his enthusiasm for the role shines through.

A smash-hit on television later sent to theaters, Caan and Billy Dee Williams co-star in this tear-jerk true story of Chicago Bears players Brian Piccolo and Gale Sayers and their odd couple-esque friendship. No wonder it’s considered a benchmark in television movie making.

This weird outing features Caan as a Chicago book editor who mistakes the title character for a prostitute, sending the wise-cracking Candice Bergen on a downward spiral. Critics said that without Caan and co-star Peter Boyle, the film would essentially be pointless. (This seemed to happen a lot, early on in his career.)

On the heels of his ‘Godfather’ success, more than a few eyebrows were likely raised by Caan’s portrayal of a Navy man stuck in limbo in Seattle, where he meets a pool hall hustling hooker-with-a-heart-of-gold (Marsha Mason) and falls in love, both with her and her 11 year-old son, played by child actor Kirk Calloway. A well-meaning little movie that did well during awards season that year.

An amusing trip back to a time when Alan Arkin and Valerie Harper could be cast as Mexican-American husband and wife and snag award noms for their performances, the main point of this cultural fossil buddy picture is the unhinged back and forth between Arkin and Caan, who play a pair of maverick San Francisco cops. Critics called it “tasteless.” They were absolutely correct, but that doesn’t mean it wasn’t fun.

Michael Mann’s sleek directorial debut served two purposes — to remind us that we were no longer in the 1970s, and to give us a lot of time to watch Caan play a cool criminal, specifically an expert Chicago safe-cracker out for one last professional thrill.