Decades before George Clooney pulled a big heist, Sinatra assembled his own Ocean’s Eleven

Film Lists George Clooney
Decades before George Clooney pulled a big heist, Sinatra assembled his own Ocean’s Eleven
Ocean’s Eleven Screenshot: YouTube

Watch This offers movie recommendations inspired by new releases, premieres, current events, or occasionally just our own inscrutable whims. This week: With Zack Snyder’s Army Of The Dead bringing zombies to the Vegas strip, we’re bringing Vegas to Watch This.


Ocean’s 11 (1960)

While younger audiences may know of the stylish, Steven Soderbergh-directed, 2001 remake (and its subsequent sequels) where George Clooney and his A-list pals pull off elaborate heists, the Ocean’s Eleven of this century was merely trying to recreate the sharp-dressed fun Frank Sinatra and his Rat Pack brethren had back in 1960. That was the year that Ol’ Blue Eyes and his mischievous band of brothers—Dean Martin, Sammy Davis Jr., Peter Lawford, and Joey Bishop—got together to play ex-soldiers planning to knock off a quintet of Vegas casinos on New Year’s Eve. They shot the film mornings, after playing two shows a night at The Sands—a schedule that somehow left room for cameos in the 1960 Cantinflas vehicle Pepe, which was shooting in Vegas at the same time. Behind the camera was All Quiet On The Western Front director Lewis Milestone, burdened with the task of reining in these jokers and reminding them they had a damn movie to finish.

The original Ocean’s plays like a smart-assed, Technicolor version of Stanley Kubrick’s 1956 heist thriller The Killing, with Sinatra leading a crew that’s more swinging than hard-boiled. These guys still lay on the problematic machismo, as evidenced by a scene where Martin’s character says he plans to take his money and get into politics just so he can take away women’s right to vote and make them slaves. But his sexist cad is no match for Sinatra’s Ocean. When he’s not coldly loving and leaving dames, he makes prank phone calls to the heist’s exasperated, Beverly Hills-based orchestrator (Akim Tamiroff). For a guy who’s supposed to be the revered ringleader, Ocean is a bonafide man-child.

Clocking in at over two hours, this Ocean’s piles on a lot. (It makes you wish Sinatra tore out more pages from the quip-filled script, which he allegedly did during one tense day of shooting.) The movie spends its first hour establishing all the main players in the crew, including Richard Conte’s dying ex-con, whose job is to shut off the power on the casinos so the jacking can commence. Angie Dickinson shows up in a couple of thankless scenes as Ocean’s long-suffering ex-wife. (She’s one of the few female characters, most of them unfortunately written as nagging shrews.) We also got a few musical numbers for Sammy and Dean; cameos from Red Skelton, George Raft, and an uncredited Shirley MacLaine; and let’s not forget Cesar Romero as the heavy who throws a monkey wrench in these guys’ plans in the last half-hour. With all this, it’s no wonder the movie kind of peters out, with a downbeat ending that shows how the Vegas strip can truly be a boulevard of broken dreams.

Nevertheless, the ’60s Ocean’s is a fascinating artifact because it shows Las Vegas still in the process of becoming the overwhelmingly glitzy, million-watt wonderland/tourist trap/eyesore that it is today. There’s none of the obnoxious opulence and billion-dollar splendor of modern-day Sin City. Back then, it was still a desert town with a few fancy hotels, complete with casinos that look like your dad’s wood-paneled man-cave. It’s no wonder Frank, Sammy, and the rest couldn’t get enough of Vegas back in the day. It still felt like home.

Availability: Ocean’s 11 is currently streaming on HBO Max and available to rent or purchase digitally Amazon, Google Play, Apple, Microsoft, Redbox, and DirecTV.

36 Comments

  • floyddangerbarber-av says:

    I think the ending to the original “Ocean’s Eleven” is pretty much perfect, cynical and downbeat, like the hangover at the end of a long weekend spent desperately partying and losing way more money than you can afford. Pure Vegas. That’s how I remember it, although, to be honest, I haven’t seen it in several years.

    • fast-k-av says:

      Agreed. I rewatched it in the last few years and I still like the ending much more than the remake. Both versions have great chemistry in some of the leads, but I could tune out in the new one when they’re all standing around the fountain and feel like I missed nothing. Sinatra’s version is compelling until the credits start rolling.

      • wakemein2024-av says:

        I just like modern Vegas so much more. It’s just as tacky, mind you, but the high ceilings and ever present air-conditioning allow me to think I’m living the high life. The casinos of the original version are the “rug joints” Hyman Roth was talking about.

      • sunnydandthepurplestuff-av says:

        There’s a certain amount of Soderbergh overkill in Ocean’s 11. And I’m aware that Clooney’s a great guy blah blah blah but at a certain point, I couldn’t stand him as an actor/filmmaker. I think his filmmaking eye is often just as egotistical outside of Ides of March.

        Ocean’s 12 was self-referencing vanity to the point where it was a major turnoff and I soured on the 5 leads for years.
        Is that what you might be referring to?

        • fast-k-av says:

          Mostly just that last scene in the remake feels like no one knew how the movie was supposed to end. It almost feels like the end to an episode of a sitcom where the audience knows that, come next episode, everything will be reset back to the status quo, which is sort of is in that 12 didn’t really bring anything new to the table (I think Ocean’s 13 was a bit better on this front). I’ve enjoyed Soderbergh off and on, The Informant was a particular favorite of mine. But as far as the actors in Ocean’s 11 go, after the first time I saw it I remember mostly wanting to see Don Cheadle in more things, a wish that’s been fulfilled many times over by now.

          • hammerbutt-av says:

            I don’t know who thought the Cheadle cockney accent was a good idea I’m guessing it had something to do with Brad Pitt having previously done Snatch. 

          • fast-k-av says:

            OH MY GOD I forgot about that. In my memory I just convert him back into sounding like regular Don Cheadle because why would he do it different. But then this was the beginning of his star rising, so I’m sure there was less pushback on the idea from all angles even though it’s extremely silly.

    • duffmansays-av says:

      The ending isn’t even downbeat. That’s how old time heist movies pretty much all end. It wasn’t until the ‘70s, when the crooks started getting away with it and maybe not until the ‘80s. I like Oceans 11, but The Killing is a classic and a much much better film. 

      • tokenaussie-av says:

        The Italian Job being the most infamous example.Of course, that movie isn’t really a heist movie, since that was just an excuse for a delightfully random car chase (done by getting one over Italian bureaucracy), and, of course, Noel Coward as a gangster. 

      • skipskatte-av says:

        The ending isn’t even downbeat. That’s how old time heist movies pretty much all end. It wasn’t until the ‘70s, when the crooks started getting away with it and maybe not until the ‘80s.That was explicitly due to the Hays Code, which included a clause that, “All criminal action had to be punished, and neither the crime nor the criminal could elicit sympathy from the audience, or the audience must at least be aware that such behavior is wrong, usually through “compensating moral value”.
        Hence, all the heist movies from the 50s through the 60s had to end with the crooks going to jail or dying. 
        It was abandoned in 1968 when G, PG, R ratings system came into effect.

        • hammerbutt-av says:

          It was already being largely ignored by 1960 I doubt Sinatra cared about upsetting them if he wanted a different ending he would have put it in.

    • macthegeek-av says:

      If you’re looking for a double feature, The Cincinnati Kid pairs very well with the original Ocean’s 11. Steve McQueen as a poker whiz, Ann-Margret as the femme fatale, and Edward G. Robinson shows up as the boss fight at the end.(Did I mention Karl Malden? Tuesday Weld? Rip Torn? Cab Calloway?)

    • the-edski-av says:

      “The deceased is being cremated” and the look they all share is an excellent ending IMO. It’s “cheaters never prosper, but damn if we didn’t have fun watching, eh?”

  • stickybeak-av says:

    “A review at the AV Club? Big deal! Now pour me another Jack Daniels and get me a packet of Camels. Unfiltered.”

  • deathmaster780-av says:

    Ugh, yeah the George Clooney remake was way better than this. Way more fun and entertaining. Also didn’t have a morality tale slapped onto the end.

    • hamologist-av says:

      100 percent with you. I don’t understand the Rat Pack nostalgia to begin with, and nothing about this movie changed that.Then again, I think this is the pinnacle of Frank Sinatra used in a film, so maybe my blown attention span and 30–plus years of brain-numbing hypercapitalist image desensitization is the problem there.

      • jhhmumbles-av says:

        The pinnacles of Sinatra in film (or films that I have seen; he won an Oscar for From Here To Eternity) are The Manchurian Candidate and The Man With the Golden Arm. Both hold up well. He could be a very effective actor when the movie was about something other than his persona/ego.

        • dr-darke-av says:

          So do From Here to Eternity and The First Deadly Sin. The Detective is a good film, too, though its attitude toward gayness did not age well…!

        • tombirkenstock-av says:

          Von Ryan’s Express is another great Sinatra film, and one of the few WWII films to take place in Italy.

        • arihobart-av says:

          Although Sinatra didn’t like it, Von Ryan’s Express is pretty good, too.

      • jstraw727-av says:

        Although that’s Sammy doing that version, not Frank…

    • tokenaussie-av says:

      I’m reminded of a Tarantino quote on remakes:“Don’t remake good films. [Soderbergh’s] Ocean’s 11 works because the original was terrible.”

  • trigdiscipline-av says:

    I really enjoyed the new Ocean’s # movies, and went back to watch this one out of curiosity. It is just an incredibly boring and tedious vanity project, an order of magnitude less entertaining than any of the later movies.

    • billyjoebobson-av says:

      from here, this perspective. it was pretty popular when it was released though…hindsight may be twenty twenty….but contemporaneous reactions have value, as well…

  • markagrudzinski-av says:

    One of the rare examples where the remake is superior to the original. As much as I enjoy the OG Rat Pack swagger, the movie is a slog… and a slog that isn’t aging well.

  • gargus-scp-av says:

    Y’all forgot the Watch This tag again.

  • smithsfamousfarm-av says:

    “Hey Josh, how do you get this stuff off?”“Hey, I…”It’s so dated, but you cannot say that’s not a funny scene. I haven’t seen the original Ocean’s 11 since I was a kid in the ‘80s, but like the better Elvis movies, it holds up (despite everything…). I’m also continually surprised that Sinatra was the star in The Manchurian Candidate. He had stage presence for sure, but he actually -was- a decent actor. Surprised he didn’t go the Elvis route and do a movie every year, if not every six months. All of the Rat Pack were great. 

    • hammerbutt-av says:

      Once he convinced the Mafia to cut off that horse’s head so he could get the part  in From Here to Eternity he didn’t squander the opportunity he worked hard and proved himself as an actor. He had several very good performances in the 50s: The Man with the Golden Arm, Some Came Running and a movie called Suddenly in 1955 where his character is planning on assassinating the President.

  • hawkboy2018-av says:

    Give me Maudlin’s Eleven any day. Skip Bittman and the Harmonica Gang over any of these shmoes.

    • hornacek37-av says:

      You beat me to it.Maudlin’s 11 was my introduction to the “11″ films.  Obviously it was long before Clooney’s version, but I had never heard of the original film when I saw this on SCTV, so I just thought it was a funny title.

  • rauth1334-av says:

    i liked the ds9 version

  • zwing-av says:

    I wish more people would take this as a lesson in movie remakes. The original is…fine? It has its moments and a certain energy. But what it really has is a solid, fun heist concept. So take that concept, get rid of everything that didn’t work, and make a better movie out of it without being slavishly devoted to the original, since the original isn’t that good!That awful Total Recall remake has been on recently and is like the opposite of Ocean’s Eleven in that respect.I do like the Eee-O eleven song though.

  • gojiman74-av says:

    I unapologetically love this movie. I first saw it many years ago as a young 20-something living on my own for the first time. It was a Saturday night in december and my GF at the time and I were making dinner and decorating the X-mas tree in my first ever apartment. Twenty some years later it become tradition that this movie goes on whatever night the tree goes up at my house. Its become one of my favorite holiday movies.

  • actuallydbrodbeck-av says:

    I prefer Maudlin’s 11

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