Ranking Every Movie George Clooney Directed, Including The Midnight Sky

5. Leatherheads (2008)

As a silly, slap-happy attempt to make a 1930s-era screwball satire, Leatherheads is an old-fashioned lark that wasn’t meant to appeal to anyone over the age of, say, 35 (or, let’s be honest, 45). It’s no wonder, then, that it flopped, but there’s a good bit to appreciate in George Clooney’s third directorial feature. While Leatherheads rarely gets its comedic timing exactly right, our leads, John Krasinski, Renee Zellweger, and Clooney, are committed to the bit, bringing spunk, sassiness, and a good sense of humor to balance out Clooney’s oddly rigid filmmaking (perhaps to mirror the stationary camerawork style at the time?). As a farce, it’s a fumble. But as a period piece, it’s filled with gorgeous sets and costumes and splashy production design. Clooney can dependably make a handsome-looking film, and he relishes recreating this lost time period.

There’s ultimately not enough here to heartily champion, but Leatherheads isn’t the type of movie you want to dismiss, either. Certainly, this triangular rom-com isn’t without its sly, sharp pleasures, even when it veers into being cutesy and/or smug.