This Friday sees the release of Iron Man 3, with Robert Downey Jr. returning to the role that took him from (hugely rewarding) indie purgatory to all-out blockbuster movie star. But there are more than two chapters to the RDJ saga, and this week the Grantland staff looks back at some of the most memorable moments of his career.

Weird Science

Michael Weinreb: The hair, the handshake, the bracelet, the nyuk-nyukking, the utilization of the term “finski”: Dude was such a spot-on dickhead in ’85 that I don’t think I’ve ever fully forgiven him.

Less Than Zero

Molly Lambert: Bret Easton Ellis disavowed it completely for a long time, but the 1987 film adaptation of Less Than Zero is actually perfect. It’s a nihilistic teen movie, and while it’s super corny in a lot of ways, it’s also weirdly soothing. It makes me feel very nostalgic because it captures superficial aspects of posh late-’80s Los Angeles so well — illuminated pools that look like David Hockney paintings, glass bricks, modernist white mansions, stiff satin bows, and neon everything. Andrew McCarthy, Jamie Gertz, and RDJ’s trio of high school friends growing apart during college are recognizable, although they are insanely wealthy and entitled. As Clay and Blair, McCarthy and Gertz’s romance is pretty flat, and Clay’s bisexuality is written entirely out, as are the novel’s scenes involving snuff films and child rape. The book’s ambiguity is tossed out in favor of a pat after-school special narrative. But it’s all held together by Robert Downey Jr.’s magnetic rich kid turned rent boy, who is the subject of everyone’s conversations when he’s not around and impossible to ignore when he is. You watch as he blossoms into the unflappably louche persona we know today. His scenes opposite equally unflappable and louche ’80s heartthrob James Spader, as Rip the smooth coke dealer, are magic.

Rick Rubin produced the Less Than Zero soundtrack, which spawned multiple hits. Despite the extremely white coddled rich kid world of the movie, the soundtrack included the first releases of Public Enemy’s “Bring The Noise” and LL Cool J’s “Going Back To Cali.” It also has Roy Orbison singing a song Glenn Danzig wrote for him called “Life Fades Away” in a collaboration dreamed up by Rubin, and the Bangles doing a killer take on Simon & Garfunkel’s “A Hazy Shade of Winter.” The Moroder-ish instrumental score is by Thomas Newman, who wrote the scores for Revenge of the Nerds, Desperately Seeking Susan, Girls Just Want to Have Fun, Real Genius, and that deathless trailer temp soundtrack, the American Beauty score.

Back to School

I. AM. IRRRRRONNNNN. MAN!
[Series of fart noises, falls on floor, begs The Mandarin to do him.]

Mark Lisanti: Kids: Look this one up. But be prepared to see Rodney Dangerfield in various states of undress and in a distressing amount of sexual situations.

Saturday Night Live

Steven Hyden: Robert Downey Jr.’s name appears three times in Tom Shales and James Andrew Miller’s Live from New York: An Uncensored History of Saturday Night Live. The first mention confirms that Downey (as nobody remembers) was a cast member in ’85-86, the single weirdest season in SNL history, when Lorne Michaels returned from a five-year hiatus and assembled a bunch of big-ish names — Anthony Michael Hall, Randy Quaid, Joan Cusack — who never coalesced and were swiftly replaced the following year. (It was the 2012-13 Lakers of SNL casts.) The second is Bernie Brillstein saying that Michaels really wanted Downey (a red-cheeked babe of 20 at the time), which “wasn’t a terrible idea, but it wasn’t a good idea either, in retrospect.” (This is probably the only charitable way to put it.) The third reference comes courtesy of fellow misbegotten cast member Terry Sweeney, who recalls Chevy Chase coming back to host the second show of the season and saying to Downey, “‘Didn’t your father used to be a successful director? Whatever happened to him? Boy he sure died, you know, he sure went to hell.’ Downey looked ashen.” So, yeah, this sketch might be definitively unfunny, but farting on a Weekend Update anchor must’ve been therapeutic, I’m sure.

Soapdish

Charles P. Pierce: His gifts as a comedian have been criminally underrated to his gifts as a dramatic actor and an even more dramatic criminal defendant. Here, in a moderately entertaining parody of the making of a television soap opera — nowhere near as good as the scenes in Tootsie on the same subject, and those were only about half that movie — he plays a producer torn between his job and his unseemly lust for Catherine O’Hara’s hospital swamp vixen, a lust that gets even less seemly at the movie’s, ahem, climax. I think he’s pretending to have a stroke here, although it seems to be centered in his upper back. The whole scene is ridiculous. Hell, the whole movie is ridiculous — Kevin Kline has a hilarious scene early on, playing Willy Loman at a dinner theater in Florida — and Downey is one of the most ridiculous things in it. Which is great because, looked at in a different way, you could say the same thing about Iron Man.

Natural Born Killers

Sean Fennessey: Wayne Gale is meant to be a send up of Geraldo Rivera–style mock-outrage, a serial killer–stalking TV interrogator, though I’m not sure screenwriter Quentin Tarantino could have predicted the hectoring goat-wail of Nancy Grace. Gale’s not meant to be prophecy; it’s satire. And RDJ abides, executing his madcap bad-Australian accent the way he does everything: too much, too good.

The Last Party

Alex Pappademas: In this documentary, an often-squirrelly Downey takes the pulse of America on what turned out to be the eve of the Clinton years by conducting interviews with everyone from Patti Davis to B-Real. Credited executive producers include Donovan Leitch and Serena Altschul, so it might as well say “Produced By The ’90s” at the top; it’s a time capsule of a moment when Gen X’s supposed political apathy was seen as an important social problem to be grappled with. Downey lies around on hotel beds, listens to Check Your Head instrumentals, ponders CIA malfeasance with help from Sean Penn. But we’re also watching Downey grappling with Downey, and that’s what’s compelling about the movie now. It’s a campaign-trail doc as covert autobiography, and sometimes it isn’t even that covert. Within the first few minutes we see Downey shaking Clinton’s hand on a rope line and offering his services as a convention speaker, followed closely by a montage of the greatest actor of his generation illustrating the dichotomy between his two personalities — “the Good Boy and the Goat Boy” — by performing a hopping satyr-dance in various contexts (under-construction Democratic Convention stage, Rockefeller Center, the woods). “It’s important to me to stress that it’s not a frog, that it’s a goat,” he explains. “I just haven’t owned it yet. If you repress the goat, then he’ll nail you.”

Your mileage may vary, but I’m kind of a sucker for documentaries and travelogues that wander away from their stated subject and end up chronicling the chronicler and/or anatomizing the chronicler’s need to make the conversation about him, and that’s what happens here. In 1992, Downey was about a year away from having his first kid, about four years from the first drug bust and the ensuing tabloid tempest. He talks onscreen about having been “to treatment,” but let’s just say his recovery seems to be very much a work in progress here. There are moments where Downey seems to already be performing community service by appearing in this movie and moments that play like the Goat Boy is still very much driving the bus, even if the only weakness he’s seen indulging onscreen is his addiction to attention. He’s funny and earnest and sarcastic and open about his own confusion and appears to be perpetually three seconds away from breaking down and running around the corner to cop an eight ball, and somehow all this (but especially that last part) makes him the perfect narrator for a movie about why we fight the impulse to disengage from reality, a question that clearly had vast non-political implications for an addict. It’s a quaint film but also a Downeyologically crucial one, no more so than in this weird, sweet scene, in which Downey hangs out with his father, underground-film legend Robert Downey, and Downey Sr. owns up to the fact that maybe letting 6-year-old RDJ toke up with him was not the best idea: “A lot of what we did to ourselves, he did, too, and he’s missin’ some fuckin’ pistons … It was an idiotic move on our parts, to share that with our children. But look, he’s OK now.”

Kiss Kiss Bang Bang

Dan Silver: I’d like to believe that kismet is what brought together RDJ and Shane Black for the first time (the second being the money-printing machine that will henceforth be referred to as Iron Man 3). Their Kiss Kiss Bang Bang is one of those little-seen and often-forgotten cinema gems. Merely liking it is not an option. The film is either ardently worshipped or vehemently loathed. The pairing of Downey’s hyperbolic erraticism and Black’s pulpy dialogue and mystery-novel framework combine to form a palpable creative sandbox for these two talents to play in. RDJ and Black’s pairing in this film is reminiscent of other blessed performer/auteur relationships — Kevin Kline and Lawrence Kasdan; William H. Macy and David Mamet; Diane Keaton (the obvious choice, but much prefer Judy Davis) and Woody Allen; and yes, even Jason Lee and Kevin Smith. There is so much fun stuff packed into this little movie that it’s almost impossible to click away when it’s on TV. And I’d go so far as to say that Downey’s Harry in Kiss Kiss is the bizzaro Tony Stark. Opposite in every way except charisma. If you’ve seen it, watch it again, if you haven’t, go find it, and it’ll be obvious that the cinema gods intended Black and Downey to find each other. And hopefully work with each other for many many many more movies. (One of which I hope is a sequel to Kiss Kiss. We all need more Harry and Gay Perry in our lives. We really do.)

Zodiac

Chris Ryan: My favorite Downey Jr. performance is his turn as journalist Paul Avery in David Fincher’s Zodiac. In the last few years, I feel like when you watch Downey you’re watching Downey the Movie Star. You’re seeing a carefully constructed, well-managed persona. But the thing about being a movie star is that people want a fixed point of reference; once you establish a few valuable qualities that millions of people are willing to invest 15 bucks in, you can’t really screw with that. It’s too valuable.

In Zodiac, Downey displayed the magnetism that would earn him roles as Tony Stark and Sherlock Holmes. But he still has enough of the career-fatalism, informed by so many ups and downs offscreen, to play a character that goes totally off the rails and never comes back. Of all the people who die in Zodiac, Avery might be the most emotionally moving casualty. His trajectory, from motor-mouthed star reporter to houseboat-bound addict, is fascinating to watch. The character feels lived in — from his hair to his mannerisms (the straws in the bar scene!) to his specific ways of dealing with different colleagues at the San Francisco Chronicle.

I picked this scene for two reasons. (1) Avengers assemble! And, (2) Downey calls Mark Ruffalo’s Dave Toschi “Bullet,” which is so cool. But I could have picked any moment he was on the screen.

Iron Man

Emily Yoshida: Talk about giving a good interview Who says that a journalism degree is worthless Are we totally sure she’s not from Vice? I got nothing. This scene renders me useless.

The Avengers

Amos Barshad: As a person whose prolific shawarma-consumption rate is only matched by his shawarma-joke-making rate, I admit, I was primed to relish this last little bit at the end of The Avengers. But beside my own undying allegiance to meat-shavings in pita (or laffa!), there’s something worthwhile here. After all that shrieking disaster footage, that tiny touch of levity, followed by that soothing touch of silence (and, OK, some chewing noises) reminded us why it was particularly nice this thing was directed by Joss Whedon, relatable mensch. But just one quibble: As the internet pointed out at the time, how is it possible that Tony Stark — cosmopolitan billionaire playboy — has no idea what shawarma is?