Today! Because that’s how Dad did it, that’s how America does it, and it’s worked out pretty well so far –
Iron Man (2008)
Directed by Jon Favreau
Starring Robert Downey Jr. (x9), Gwyneth Paltrow (x5), Jeff Bridges (x3), Jon Favreau (x4), Terence Howard, Clark Gregg (x5), Leslie Bibb, Shaun Toub, Faran Tahir, Paul Bettany (x3), Peter Billingsley (x2), Samuel L. Jackson (x11), Tim Guinee
There aren’t a lot of years with multiple films still to come on this list, but 2008 leads the way so far as the top 38 are concerned. 1994 still has three – with the next one arriving on Wednesday – and has already seen seven films make it, but 2008 has four in this group starting today. More surprisingly, maybe, is that there have only been three up to this point – #204 Semi-Pro, #322 Role Models, and #352 Be Kind Rewind. Huh! Saving the best for later, I guess!
But man did I love the summer of 2008. I moved to Chicago at the end of May, living within walking distance of a movie theater for the first time in my life – Shoutout to the Webster Kerasotes! Changed hands but not forgotten! – reunited with the girlfriend after 21 months of long distance relationship-ing, reunited with my high school pal Dave, and basically dragged them to see everything that came out, multiple times. I’d like to say that this was just a hectic adjustment period where I overindulged in cinema-going, but no, this just showed me what my life would become here in the big town. Having moved twice since, I still have never been more than an eight minutes walk from a theater.

Can’t find a picture of the outside, and inside the Webster Kerasotes looks like every other theater ever
Iron Man was already in theaters when I arrived – I want to say I first saw it in Chicago, though, as I’d come out a bunch of times in the preceding months to look for apartments and such. That summer also marked the beginning of our long running Box Office Pool, extensively chronicled to this day (as of this writing) at http://www.boxofficepool.wordpress.com. To explain very quickly, we split the year into the Summer and the Fall/Spring, and thus hold twice yearly drafts of upcoming movies, the winner tallying the highest total box office gross. Pool 1 was legendary, what with the surprise hits (my Iron Man), the surprise super blockbuster (Dave’s The Dark Knight, people seem to forget, was hardly the most anticipated movie of that summer), and the solid grossing/hugely disappointing #1 pick (hello, Indiana Jones 4). As of this writing, we’re winding down Pool 22, and assuming we have continued on into our twelfth year of competition, as you read this we should be in the midst of Pool 25! Go see who’s in the lead right now!

Here is the whole pool gang, at either the second or third draft in my first Chicago apartment – me, Sarah, virtual Nick, Sam, and Dave
And little did any of us know that Iron Man would become basically the most financially important film ever made. Sure, it was merely the third highest grossing movie of that year, but imagine if it came in around initial expectations, and tallied like $170. How does the MCU look four years down the road from that? Is there really excitement, or is it not unlike the first four years of the lousy DC Universe of movies, with their lackluster Man of Steel/Batman v. Superman/Justice League bullshit? Do things get adjusted on the fly? Is a Thor movie really the right decision for the first non-Iron Man stand alone (because, you’ll remember, Tony quickly appeared at the end of the Hulk film in 2008)? I remember for years there were rumors that Tom Cruise was going to play Tony Stark, and I mean, you can see that, right? But would that have been different or interesting enough to jumpstart a mega-franchise that as of this moment has grossed $18 billion dollars worldwide?? That’s not an exaggerated figure, like me saying Indiana Jones 4 sucked a million dicks – the MCU movies have literally amassed $18,000,000,000, as of right now. And it’s almost entirely thanks to Robert Downey Jr.
That’s not to take anything away from Jon Favreau’s solid direction, the terrific origin story script credited to four different people, Jeff Bridges’ great villain work, or Gwyneth Paltrow’s work as the long suffering Pepper Potts, but none of this would’ve meant anything without the great resurrection story and boundless charm of RDJ as the egomaniac death merchant turned superhero. This is now Downey’s ninth appearance on this list, and more than half of those are pre-Iron Man, so I was squarely in the camp as a fan from way back, but I don’t think anyone figured he could pull his life and career together to this degree. What a great story! And what a great merging of actor and character! It’s an amazing, lightning-in-a-bottle success story, and you have to sort of sit back in awe that they had the balls to put it together.
And it’s still great – even in a series as crazy long in the tooth as this one, with so many different directors and characters and terrific entries, I’d still hold it up as the best actual movie of the bunch. Most fun? Most exciting? Maybe not. The majority of the films weren’t eligible for this list, thus only this, #265 Iron Man 3, and #224 The Avengers made the cut (sorry, Captain America fans!), but a bunch from the past five years certainly could’ve in years to come – Thor: Ragnarok, Guardians of the Galaxy, Captain America: Civil War, and Black Panther for sure, some of the others possibly too. But Iron Man 1 is still the top of my quality list, and probably right there in the top four or five superhero movies ever made. And I owned approximately one Iron Man comic in my entire life.

This one – I don’t remember what it’s about, and I’m not sure where it is now, but as a child I only had like five comic books, bought at a grocery store, and this was one
Downey becomes the fourth Nine-Timer, joining Frank Oz, Bill Murray, and our new Eleven-Timer thanks to his brief, pivotal cameo at the end of this film, Nick Fury himself Samuel L. Jackson! Time is really winding down on this contest, and Sam Jackson isn’t done yet! Can he hang on to this lead? Exciting!
Coming tomorrow! Listen Betty, don’t start up with your white zone shit again –
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