Almost a decade after its release, it would be hard for me to call The Italian Job remake anything else but great. I don't really think it is a particularly profound film, but it represents exactly why people started going to the movies: to be entertained. It is a film that I have watched over and over since its initial release, to the point that is has become the cinematic equivalent of comfort food. Like Star Wars, or Indiana Jones, it is one of my frequent viewing choices if I am sick or having a bad day. But what makes this remake so infinitely rewatchable? It might be because it's a movie that knows that it is trying to be cool, but also knows that trying to be cool is inherently uncool.* It also helps that the film manages to balance this commentary with a satisfactory series of ending setpieces and a satisfying resolution.
The film's villain, Steve, played by Ed Norton, is so banal that he acts as a commentary on derivative genre exercises. Frequently told he lacks imagination, he "couldn't even decide what to do with all that money, so [he] had to buy what everybody else wanted." Considering that The Italian Job itself mostly follows conventional heist film structure, this is almost a form of meta-irony, where the film comments on itself ironically, but still proceeds without this commentary interfering in the sincerity and execution of the film itself. Basically, it winks and nods at the form (heist film) of art it is, and then demonstrates how a tweak on a common formula is still satisfying to the audience by getting out of its own way once the actual heist in the film gets underway.
Another key scene in which the film does this is when "Handsome" Rob (Jason Statham) uses his masculine charm to set himself up with a female cable company employee. While he does this, Lyle (Seth Green) provides commentary attesting to the unreality of actually attempting to do this:
While acknowledging the ridiculousness of what is happening in the film, it doesn't have it backfire, either. "Handsome" Rob has a nickname for a reason, and this is well within his powers, both trading on the growing persona of Jason Statham (fresh off the first Transporter film at the time) and adding to it.
Other minor points like this include ending the opening heist with a cover of Pink Floyd's "Money" by Velvet Revolver. A cover song establishing the tone of a remake, and by a band that is a mash-up of two other bands. Perfect choice.
None of this would matter, of course, if the film wasn't successful at also trying to be a slick, cool heist film. The actual heist itself is very fun, and of course it doesn't go as planned, with a series of escalating obstacles. The twists and turns are fun, but I think a lot of what makes the chases fun is the on-location shooting in both Venice, Italy, and Los Angeles (and a few minutes in Philadelphia!).
This has been a bit all over the place, but I think it is worth thinking about the films closest to us, and why they resonate so much.
*This is in direct contrast to another early 2000s remake of a 60s film, Steven Soderbergh's Ocean's 11, arguably the coolest film of all time.