The Movie Room

Ocean’s 11 1960, directed by Lewis Milestone

Rating: 6/10

I love a good heist movie, including the Ocean’s movies. I grew up watching and rewatching (and rewatching and rewatching) the George Clooney and Brad Pitt trilogy, and when Ocean’s 8 came out I was very into it and get excited whenever I’m in a hotel and see it while skimming the channels (and I occasionally put in my copy of it). The original Ocean’s film starring the Rat Pack is very similar to the modern version, both for better and worse.

The storyline is pretty much the same—Danny Ocean (here played by Frank Sinatra) gathers a group of con artists to pull off a casino heist, this time on New Year’s Eve! The tech used in the 2000s version is cool and allows it to be kind of similar to a more relaxed Mission: Impossible movie, but even though this came out around the time of the TV versions of Mission: Impossible, Get Smart, and other spy shows, it never really feels like them and instead just relies mostly on good thief planning. This is why I love old heist movies especially, as they are more about the con than about the tech. I love Simon Pegg in the M:I movies, but when he gets out from behind a computer I love it even more, and the Rat Pack in Ocean’s 11 are always out and bantering amongst each other as they pull off this cool heist. The one time where the time-setting hinders the film is that whereas now we can enjoy watching the rich get screwed out of legally-but-unscrupulously-gotten gains, in 1960 there still seems to have to be a moral lesson and so we don’t end with the same great way the remake ends, cheesy as that still was. The end here is still good, but it left me disappointed, like cheap champagne on New Year’s Eve.

Another similarity between this version and the Soderbergh remake is that the cast seems to be having a great time, which is definitely a feature of every movie starring the Rat Pack. Sinatra, Dean Martin, Sammy Davis Jr., Peter Lawford, and Joey Bishop are all very familiar with each other and with the audience so their dynamic feels very comfortable. It never feels realistic to the characters in a way that lets you actually believe the movie is actually caring about that kind of thing, but sometimes it is just fun to watch cool people having a good time together—that is also the appeal to a lot of Adam Sandler movies recently as he and his friends just seem to use their movies as paid vacations. Because of the generation I am from, I have more fun watching Clooney and Pitt and their costars having fun, but it is still a good time watching Sinatra and co. Cesar Romero isn’t usually part of the Rat Pack, but he also looks like he is having a great time here and I love that for him as well. 

For me, this sense of fun behind the scenes does stop the movie from really being “great” when it doesn’t really translate fully into a cohesive narrative, but sometimes it is just fun to watch celebrities having fun. The Clooney version is still my go-to Ocean’s film, but this original is still fun, and admittedly a better movie than Ocean’s Twelve.