Updated RankingBreezy (1973)
★ ★ ★ - OkayThis should’ve been terrible. Romance between old, withdrawn businessman (William Holden) and young hippie (Kay Lenz) is problematic at its foundation. Eastwood doesn’t back off from or dance around the problem, giving Breezy enough life to not be a manic pixie dream girl. Holden is in top form and Lenz easily matches him here in terms of star quality.
The Eiger Sanction (1975)
★ ★ If your character is supposed to be an irresistible sex machine, it might play better if you don’t direct it. Eastwood can deflect and downplay as much as he wants, but there’s a required level of desirability and every time he plays into it it’s a major ego trip and/or monumentally embarrassing to stand before the camera as an alpha male. Add to that, Eastwood is playing an expert mountain climber, which also evokes a lot of masculine confidence.
The film is constantly problematic, such as the flirtation with a black woman named Jemimah Brown that trades racial humor as foreplay. (She makes a rape joke before jumping him.) There’s a gay character whose dog is named a homophobic slur. See it’s supposed to be okay because of context, but these moments pack too much cringe into the otherwise sharp dialogue. There’s a good espionage film here, but here are the early signs of Eastwood making obvious, critical blunders.
Bird (1988)
★ ★The slog I was fearing. Perhaps if I was interested in Charlie Parker or Jazz music, but this isn’t made to bring in outsiders. It’s a celebration by a fan that avoids the biopic trap of connecting the music to the man. The two just happen to coexist. I was more engaged by Parker’s wife Chan (Diane Venora) who led a richer, complicated life that Parker was a part of.
Midnight in the Garden of Good and Evil (1997)
★ ★ ½ A very different Eastwood from the troublesome Eiger Sanction. Here he seems to not understand the moral outsiders, but he allows them to exist in a way where we laugh with them and not at them. Unsuccessful in a number of ways – and I’m not going to pull Kevin Spacey into such a short opinion – but it has the delicious vibe of an eccentric murder mystery brought off by a campy cast that I’m often fond of. Special shout out to Australian actor Jack Thompson, who never got such a substantial role in an American film.
Hereafter (2010)
★ ★This is why I gave up on Eastwood. A fantastical tale with sweeping emotions told in such a minimalist, unadorned style that I spent much of the time wondering what the point was. What am I supposed to be feeling about these people? About this journey? Eastwood seems more concerned with coming in on time and budget than giving the script the direction it’s thirsty for.
Hereafter put me off wanting to continue, with two films to go. I started J. Edgar and DiCaprio’s performance was fake inside and out. What’s left is that and Jersey Boys, and I’d rather get into some other projects this month.