‘You Like My Prison Prada?’: Anthony Michael Hall Shares An Emotional Story About Visiting Robert Downey Jr. In Jail, And How His Friend Had ‘The Greatest Second Act Ever’

When you have been in the entertainment industry as long as Anthony Michael Hall, you tend to collect stories that would make fans’ heads spin. From his earliest days playing Rusty Griswold opposite Chevy Chase in National Lampoon’s Vacation to his historic run in a string of John Hughes films, Hall got the chance to collaborate with several greats. And that streak continued during his impressive career, as he stayed active in film and television, and recently found himself part of both the Halloween franchise (with David Gordon Green at the helm) and now in the popular Jack Reacher series, a highlight of the options on Amazon Prime Video.

One early co-star of Anthony Michael Hall’s has gone on to epic levels of stardom: Robert Downey Jr., who appeared with Hall in 1985’s Weird Science, 1988’s Johnny Be Good, and as a short-lived castmember on Saturday Night Live. They came up through the entertainment gauntlet together, and according to Hall, stayed friends over the years. They even tried to reunite for a project back in 2016 (which may still have a shot at seeing the light of day). Not surprising, when you go through early stages of stardom together. It tends to form bonds that are hard to break.

Anthony Michael Hall

(Image credit: Photo Credit: Mark Binks)

So, when given the chance to speak with Anthony Michael Hall on behalf of Trigger Warning, a new Netflix movie starring Jessica Alba, I had to bring up Downey Jr. and his recent Oscar win for Oppenheimer. I assumed that Hall would have some warm memories of his long-time friend and collaborator finally receiving recognition for his enormous skillset. And Hall did share with me how he felt seeing RDJ’s win, saying:

Oh, dude. Incredible. And the fact is, when he shouted me out… we were watching the SAG Awards, when he shouted out a list of actors that he loved and who inspired him. And (I) was one of the first names he mentioned. That was incredibly gratifying for me, personally. But just to see his success, I mean, honestly? Not only the greatest comeback story in the history of Hollywood, but maybe in any business. It's up there. It's epic. His life story is epic. … He's been a great friend since then. He and his wife are great people. I love Robert. Just a brilliant guy. Honestly, the greatest second act ever.

Watch the moment for yourself right here. It was one of many stops on the long awards marathon that Robert Downey Jr. made on behalf of his work in Christopher Nolan’s Oppenheimer.

Robert Downey Jr. wins Male Actor in a Supporting Role | SAG Awards - YouTube Robert Downey Jr. wins Male Actor in a Supporting Role | SAG Awards - YouTube
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But as Anthony Michael Hall knows (and as we all know), Downey went through his down times. In the 1990s, he was arrested and charged with drug and weapons charges, and spent 15 months in prison starting in 1999. RDJ since has been pardoned of his convictions, and he of course has seen a career rejuvenation thanks, in no small part, for his dynamic casting as Tony Stark in Iron Man.

And as Hall rejoiced over Downey’s accomplishments, he remembered being there for his friend during that dark time. As Hall went on to tell me:

I remember going, when he was in prison, I went to go see him. … The moment I get there, whatever that was, 20 years ago, I walk into the yard and I literally see Downey there, right? And this is when he was going through that shit, 30 years ago, whatever it was. He looks at me, and he's got his uniform on. He goes, ‘You like my prison Prada?’ Next thing you know, we're in the mess hall, and I'm buying him a cheeseburger through one of those machines, you know? And it was so… what this guy's been through, he's been to hell and back.

It speaks tremendously to the talent, willpower, and fortitude of both Anthony Michael Hall and Robert Downey Jr. that they have survived and thrived in the often fickle business of film. And they’re finding ways to reinvent themselves, as well. You can look for Hall in Trigger Warning, which starts streaming on Netflix beginning on June 21.

Sean O'Connell
Managing Editor

Sean O’Connell is a journalist and CinemaBlend’s Managing Editor. Having been with the site since 2011, Sean interviewed myriad directors, actors and producers, and created ReelBlend, which he proudly cohosts with Jake Hamilton and Kevin McCarthy. And he's the author of RELEASE THE SNYDER CUT, the Spider-Man history book WITH GREAT POWER, and an upcoming book about Bruce Willis.