Ben Stiller and Robert Downey Jr. in 'Tropic Thunder'
Credit: Everett Collection

The summer of 2008 broke history, and rebuilt it. America suffered through a bitter presidential election on the road to a globewrecking financial crisis. In theaters, cinematic generations were rising — and falling. Superheroes, Will Smith, George Lucas, Guillermo del Toro, Emma Stone, Mike Myers, Sisterhoods and Step Brothers, Batman, and ABBA, adaptations of TV shows we still tweet about, new installments of movie franchises studios won’t stop rebooting: everything Hollywood was before, alongside everything it still is.

In our weekly column Two Thousand Late, we’ll explore the big hits and curious flops from a summer that has never really ended. Next week: Summer ends and a new era dawns with The House Bunny. This week: critic at large Leah Greenblatt and TV critic Darren Franich on Tropic Thunder.

DARREN: We’ve revisited a lot of movies this summer, Leah. But I have to admit, nothing made me more anxious than the prospect of rewatching Tropic Thunder.

For director-star Ben Stiller, this was magnum opus territory: A big-budget comedy about big-budget excess, stuffed with hard-R ultraviolence and offensive-on-purpose material. Stiller was an influential cult-comedy voice in the ’90s before he became a full-blown franchise-launching megastar across the 2000s. On Thunder, he assembled an all-star lineup from across the cinematic universe of humor: fellow comedy star Jack Black, Apatow-adjacent Jay Baruchel and Danny McBride, stand-up Brandon T. Jackson, eternal “he’s much more popular in Britain” talking point Steve Coogan. And that’s not to mention Tom Cruise under heavy makeup, Robert Downey Jr. under heavy makeup, and Matthew McConaughey in the wilderness years.

Tropic Thunder was a phenomenon upon initial release. It was the movie that finally pushed The Dark Knight off the top of the box office, maintaining a No. 1 position in domestic theaters through Labor Day. And thanks to Downey, it became the rare comedy hit to receive Oscar attention, earning the star a Best Supporting Actor nomination. Downey’s role-within-a-role might be the big talking point here. As a vaguely Crowevian method actor Kirk Lazarus, Downey spends most of the movie exhibiting “pigmentation alteration” — meta-blackface, basically.

It seems impossible that any actor would play a role like that today, though on some level “wouldn’t happen today” is the vibe of the whole movie. Tropic Thunder opens with a comedy assault, fake trailers, fart symphonies, aBrokebackish Oscar parody, the sight of Stiller’s hands exploded into Sarlacc-y stumps. The opening scene openly quotes Platoon and Apocalypse Now, two films which symbolize an earlier era of auteurist overreach.

You’re primed for a scathing satire of Hollywood…and then the film never really lives up to that prologue. There are some isolated bits in Tropic Thunder I really enjoy. I forgot just how fully committed and semi-psychopathic Jack Black was in the part of a druggy tabloid star. On some deeply pathological level, I will always think it’s hilarious when Tom Cruise says bad words. But there’s something a little backpatty in the film’s tone, halfway to Entourage. You feel everyone’s very proud of everything they’re getting away with — and the fact that Stiller ends Tropic Thunder with his character’s Oscar victory feels like meta-narcissism falling backwards into light egomania.

What was your experience watching Tropic Thunder this go-round, Leah?

LEAH: Mine was the same honestly, though maybe I enjoyed it just a smedge more than you did? Or the first 45 minutes at least; much like Ben Stiller’s biceps, the last hour is the kind of swole that you makes you think, “That is a whole lot of effort, for my mere mild amusement.” Especially when you remember that this is the same director who made his debut less than 15 years earlier with Reality Bites, where his character purposefully represented all the smash-cut emptiness of modern pop culture that Winona and her scrappy little band of gas-station bohemians were trying to get away from. The student has become the blaster.

But there are so many moments in Thunder that I still love, too: the loony cameos (don’t tell me that Tobey Maguire’s performance as the homoerotic priest in the Kirk Lazarus trailer-within-a-trailer doesn’t deserve at least a Cable Ace award), Jack Black and his jellybeans; Danny McBride’s reverse lightning-bolt mullet; RDJ’s “never go full retard” speech. And you’re so right, even rewatching that speech scene alone on my laptop, I felt uncomfortable; I don’t feel great even typing the words now. But there is real Academy wisdom in that speech too — and his delivery is perfect.

I actually enjoy this Downey performance way more than anything he’s done in spandex over the last few years; it’s so goofy and free. But to me the biggest revelation in this movie is probably Tom Cruise — not strictly because of the acting, necessarily, or the fat suit, though he works hard for both, but just that this is the last time I remember him distinctly not playing himself. He’s a hairy-knuckled bear-daddy Diet Coke-head with a nuclear rage problem, and he looks like he’s having so much fun. I don’t know that I’ve enjoyed him this much as a pure actor, and not as a dude playing the dude who is always Tom Cruise™, since Magnolia.

I also just realized, is there a lady in this movie with a line of dialogue besides “Please hold”? Not that every script has to pass the Bechdel test, but man that is a low ratio, when secondhand Maria Menounos on a closed-circuit TV beamed over the hotel breakfast buffet is your main female.

DARREN: You’ve also got Tyra Banks, Christine Taylor, Jennifer Love Hewitt, and Alicia Silverstone in steadily more cameo-ish cameos. Which could be the point! Like the same summer’s Step Brothers, the overriding vibe here is dudely self-destruction. Stiller wrote the screenplay with Etan Cohen and (hello!) Justin Theroux, and it almost feels like they aligned their core characters with the Seven Deadly Sins. Stiller’s Tugg Speedman envies Lazarus. Lazarus is a white actor prideful enough to think he can play a black man. Black’s Jeff Portnoy is a glutton, like a chocoholic, but for heroin. Grossman’s greedy. Brandon Soo Hoo’s teen guerilla Tran is all wrath. And, um, is that seven yet?

In a lot of ways, this movie seems like the apex of a particular moment in comedy, sitting alongside 2005’s dirty-joke shockfest The Aristocrats and 2006’s Borat feature. Back then, it felt like the point of movie comedy was to push past every possible barrier of good taste. (This was also the era when the horror genre slipped into torture porn, a correlation proving nothing except that the 2000s were a weird, dark time.) It’s a kick to see how far Tropic Thunder wants to push itself, no doubt. Along with the “full retard” speech (god help me, I laughed again!), there’s that bit when Grossman decides the best business move is to let his lead actor die.

We’re halfway to Network territory there — but you feel the kid gloves come on after that, like the movie can’t gettoo sharp in its showbiz satire, like there’s this quality of safely laughing with instead of dangerously laughing at. I guess it’s a tricky question of our age, Leah. Even when a movie explicitly sets out to deconstruct powerful Hollywood men, will it inevitably wind up celebrating them? It looks fun to be a powerful asshat! It’s like that old Francois Truffaut line, how there’s no such thing as a truly anti-war film, because war inevitably looks awesome on the big screen. I know, I know, quoting Truffaut now are we?, but that could be some ultimate point of Tropic Thunder, too. These dudes go to the jungle looking to make a sober war epic, lose their movie, lose their minds, and still wind up with awards-y financial success. Huzzah for failing upwards!

Cruise as Grossman is a delight. Also, maybe we’re just all the way through the rabbit hole here, but I forgot how much I enjoyed McConaughey as Stiller’s agent! I’ve just seen a lot of his Serious Face stuff post-McConaissance, so it’s a kick to watch his anxiously fratty agent face off against magisterial Grossman. Can we reunite these two characters in a spinoff? Written by, like, Tina Fey?

LEAH: Darren, this is in my top-three McConaughey performances for sure; my Mconaugh-three. He’s not doing Kate Hudson romance or gaunt Oscar bait, but he is acting out the perfect flipside of his ’90s John Grisham types: he has a noble cause and he will fight to the death for it! Except the cause is the Tivo clause in his client’s set rider, and he will fight unless the death of that client means he gets his own G5.

It’s funny what you say about the movie pivoting from satire to self-congratulation, because as two people who work adjacent to show business (and by “adjacent” I mean, like, the seagulls in the dumpster behind the Dorothy Chandler Pavilion), do you think you and I are more susceptible in general to this kind of inside-baseball shenanigans?

Thunder’s whole plot obviously hinges on some knowledge of Hollywood self-regard, but it’s not setting a super high bar: Any steady pop-culture consumer would recognize those tropes (like the opening string of fantastically bad fake trailers); they’re like an action-movie amuse-bouche that Stiller and Theroux gave us eight years before Deadpool.

Now that you brought up Tina Fey though, the script does feel like a sort of feature-length cousin to one of her and Amy Poehler’s Golden Globes monologues: a big, winky pin in the bloated balloon of industry ego. I think they might be better at it than Justin Theroux — but of course 10 killer minutes onstage is not the same as sustaining a whole movie. (And 10 great minutes is about exactly what Sisters had.)

As far as men being both the only target and, in the end, the only heroes here, Cruise’s turn did make me think for a minute about another one of my favorite left-field casting coups: Tilda Swinton’s ruthless lad-mag editor in Trainwreck. She’s just pure, venal joy with no real redemption arc at all, and I loved that.

I’m not really sure how to end this thing, so I’ll give you the one of the seven deadly sins you missed: Sloth! I’m tapping out. But I’m glad this assignment made us rewatch and reconsider a movie I probably wouldn’t have gone back to without, say, a long weekend in a log cabin with a very limited DVD collection.

My final takeaway is: Brandon T. Jackson is underrated. Cruise and McConaughey definitely need to get weird more often. And if there’s going to be any kind of spin-off, I vote for RDJ and Kate McKinnon just jabbering their crazy Australian accents at each other for two straight hours. Fin.

Complete Summer 2008 Schedule: