For a long time, Clint Eastwood’s directorial career was seen as a lark, an indulgence to keep a movie star happy so he’d occasionally acquiesce to playing Harry Callahan again. Across his first twelve films as a director, Eastwood’s films garnered scant attention from the Academy. There were only two nods bestowed on his collected output: The Outlaw Josey Wales was nominated for its score, and Heartbreak Ridge was a sound nominee. Eastwood was a guy who made moves — or, in his preferred parlance, pictures — usually for his to also star in. He wasn’t an auteur.

Bird, Eastwood’s thirteenth film as a director, was the beginning of the perception shift about his skill and intent, though skepticism still abound. A passion project stemming from Eastwood’s love of jazz music, the biopic about Charlie Parker was a lauded contender at the Cannes Film Festival, where lead actor Forest Whitaker took a prize. Tellingly, Bird was one of the first films Eastwood helmed without acting in it. The only other time that had happened up to that point was the largely forgotten 1973 romance Breezy. Eastwood’s absence from the cast list combined with the film’s decidedly marginal commercial prospects to give the impression that the grizzled veteran was moving into a different mode. Two years later, in 1990, Eastwood fell into the classic one-for-the-studio-and-one-for-me model, directing the the arthouse filmmaking drama White Hunter, Black Heart and the hideous buddy-cop action comedy The Rookie back to back. The films were released within three months of each other. The commercial play flopped, and the more serious outing was warmly received by critics but still left the awards-giving bodies flummoxed about how to deal with the action hero’s burgeoning artistry.

Eastwood’s next film shrewdly combined the kind of audience-pleasing fare he was known for and the more artistically satisfying film he increasing wanted to make. Unforgiven, written by David Webb Peoples, was a script Eastwood held onto for about a decade, waiting until he aged into the lead role of William Munny, a retired gun for hire made existentially weary by his days dishing out mortal wounds. A deeply complex story, Unforgiven allowed Eastwood to demonstrate the greater facility he’d developed with nuance while locking into the comfortable rhythms of genre filmmaking he knew so well (Unforgiven was the fourth Western Eastwood directed, and at least two other films — Bronco Billy and Honkytonk Man — borrowed from the classic Hollywood genre).

The high quality of the screenplay also allowed Eastwood to assemble a far stronger cast than in his preceding films, many of which were peppered with Eastwood pals and partners who were undoubtedly pleasant for Eastwood to have around but had noticeable shortcomings as screen thespians. Of key importance was getting the right actor for the main antagonist, a morally corrupt sheriff known as Little Bill Daggett. For the role, Eastwood wanted Gene Hackman. The impediment was Hackman’s recent decision to steer clear of films that relied on violence in their storytelling, and Unforgiven had plenty of violence. Eastwood managed to convince Hackman that the goal of the picture was to offer a realistic depiction of the physical, emotional, and spiritual carnage wrought by these venerated gunslingers, to offer a deconstructionist take on the myth-making of of the traditional Hollywood Western. Hackman came on board, and the film’s impact is almost unthinkable with any other actor in the part.

Eastwood was a famously unfussy director, refusing even the mild intrusion of calling “Action” and “Cut.” Part of that process meant that he often got out of the way of the actors, letting them shape the performance without excessive input — or much input at all — from their director. When the film hinges on a ringer like Hackman, especially with an astutely crafted role — that hands-off approach looks like genius. Hackman somehow finds his way to a tone that is best described as likable menace. Little Bill operates with the relaxed authority of the unchallenged cad. He’s the steely anchor to a powerhouse film. Hackman won his second Oscar for the performance, part of a breakthrough night for Eastwood with the Academy. Unforgiven notched nine Oscar nominations, winning four trophies overall, including a directing prize for Eastwood and the top honor of Best Picture. And there was a clear sense Eastwood was welcomed fully into the club. He was now a director whose next work was always a presumptive Oscar player.

Partially because of that awards-season attention, Eastwood was now also a director who major actors scrambled to work with. His cast list were stacked with accomplished performers, whether the movie was ambitious or kinda trashy. Often, it was hard to tell the difference between the two. At heart, Eastwood is attracted to potboilers, connecting most clearly with material that burbles with dark intrigue. The next time he directed actors to Oscar wins, critics knocked each other over to offer the loudest, clearest praise for Eastwood’s supposed emotional intricacy. But I think Eastwood wasn’t really interested in any of that gunk when he made Mystic River. He liked the page-turning intensity and simplified morality in Dennis Lehane’s story (adapted for the screen by Brian Helgeland) about cops and crooks enmeshed in a murder mystery heavy with the weight of longtime kinship.

Again, though, Eastwood had ringers to bring more layers to the straightforward material. Or if not layers, then at least a lot of top-intensity emoting, which Oscar voters often mistake for great, complicated acting. It helped that the actors in question were also, in different ways, considered overdue for the official ratification of Oscar adoration.

Sean Penn was one of the performers who occasionally held the best-actor-of-his-generation unofficial honorific that is passed around freely, especially to those who are somewhat difficult and can draw a straight line Marlon Brando in their onscreen affections. In Mystic River, he plays Jimmy, a former criminal whose attempt to keep his life on a straight-ish and narrower-than-it-could-be path is knocked askew when his teenaged daughter (Emmy Rossum) is murdered. The tragedy gives Penn the chance — hell, the dramatic necessity — to glower, brood, wail, and fume, all of which he does impressively. Again, it feels like Eastwood’s touch is a light one. He hired Penn because he was capable of their big, swooping strokes. Eastwood naturally lets him do it. It won Penn the first of two Oscars.

One of Penn’s costars was similarly awarded, and it again felt like a gesture of appreciation for what had come before as much as anything else. Eastwood likely also hired Tim Robbins because the part was in a familiar zone, a dull-witted, earnest fellow. Robbins’s character gradually becomes the main target of Penn’s onscreen ire, edging towards the film’s bleak, frontier-justice final act. Eastwood leans on the likability Robbins earned over the years to give the film’s culmination added oomph, and it comes across less as smart strategy than unfortunate shortcutting. Where Penn prospers tapping in familiar raw rage, Robbins struggles to find a center to the character. Eastwood leaving Robbins alone results in him being stranded.

One year later, for the 2004 film year, Eastwood’s directing again sent two different performers to the stage to collect Oscars. As usual, the combination of choices was defined by strong, but obvious, casting and mostly allowing the actors to taking batting practice swings at pitches they know are coming. For the boxing drama Million Dollar Baby, Morgan Freeman plays Eddie “Scrap-Iron” Dupris, an assistant a box gym run by cantankerous Frankie Dunn (Eastwood, naturally). Freeman narrates the film and generally serves as its moral compass, more device than character. As a friend of mine remarked at the time, it’s a part Freeman could do in his sleep, and there are a few scenes where it seems like somnambulant acting is precisely what’s happening. For good or bad, it’s a quintessential Freeman performance, so it’s perhaps fitting he won his sole Oscar for it.

The other acting winner that night is more interesting. Hilary Swank is perhaps unique among two-time Oscar winners in that both trophy-nabbing performances are resoundingly deserving — in each instance, the performance might be the very best of the year, regardless of category — and most of her other screen turns are lacking, to a puzzling degree. As Maggie Fitzgerald, Swank brings a thrilling emotional cunning to the performance, carrying the character through self-discovery and slowly building confidence. The physicality of the role, as is often the case in boxing films, is easy to focus on, and Swank is convincing, even thrilling, in that aspect. She refuses to lapse into mere brutish posturing, which would be enough to carry the role. Instead, she digs into the humanity of the character. No matter the scene, Swank plays the person first. Maybe because she has most of her scenes with Eastwood, and she manages to draw out a mentoring warmth in him more than most acting collaborators, Swank gives the makes it seem like her performances is stirring by his direction more than is often the case. Other Eastwood-directed Oscar winners seem like they were drawing on their own toolbox. Swank, without diminishing her own considerable talent, feels like she’s triumphant because she’s a collaborator.

It’s a common trope that actors-turned-directors give their cast members the leeway to do their their best work. Eastwood’s string of acting Oscar winners suggests that theory just might be sound.

To find about more about the premise of this series, check out the introduction. For other entries, click on the Actors Director tag.