Perhaps you’ve seen the poster for Ella McCay and marveled at its title character, a woman who’s clearly trying to Have It All—by which I mean she’s futzing with a high heel while wearing a sensible overcoat and dress. James L. Brooks’s new film, his first in 15 years, feels like a throwback to the kind of light dramedy Hollywood doesn’t make anymore, a movie where the stakes are no higher than finding a balance among work, love, and family. Brooks is the aging master behind triumphs of that genre such as Terms of Endearment and Broadcast News, but those were made in the 1980s. Can Ella revive his magic in a contemporary setting?

The answer is no, but on a technicality: This strange, shaggy movie is actually a period piece, tellingly set in 2008, a time of both hopeful promise and material misery for Americans. It follows Ms. McCay (played by Emma Mackey), a driven, idealistic 34-year-old lieutenant governor of an unnamed state who finds herself having one of the wackiest weeks of her life. Her boss, a beloved, aging governor (Albert Brooks), is accepting a position in President-Elect Barack Obama’s Cabinet, giving Ella his job. But her husband, Ryan (Jack Lowden), the useless scion of a local pizza magnate, has inadvertently dragged her into a minor scandal. Her brother, Casey (Spike Fearn), is an agoraphobic shut-in failing to confront his mounting mental-health crises. And her philandering absentee father, Eddie (Woody Harrelson), has decided to pop his head back into her life and beg forgiveness.

Brooks’s screenplay makes ample space to dump praise upon its protagonist while bemoaning her many predicaments. The narrator, her secretary Estelle (Julie Kavner at her raspiest), opens the film by sitting down in front of the camera and monologuing about how she just loves Ella McCay. A longtime Brooks collaborator, Kavner is basically functioning as his stand-in as he presents an extended ballad of Millennial promise and Boomer failure. Ella is something of an off-putting try-hard, a do-gooder brimming with policy ideas while possessing no sense of how to achieve what she wants. She’s surrounded by horrible older role models and being handed their mess to clean up—and Brooks just loves her for it.

Will audiences? It’s hard to deny that Brooks’s storytelling style, where characters trade long, flowery speeches loaded with piquant one-liners but light on realism, has grown somewhat unfashionable. His past two filmmaking efforts, the family comedy Spanglish and the sporty rom-com How Do You Know, were overlong and unfocused, burdened with narrative tangents. Ella McCay is trying harder on this front, keeping its run time to a trim (by Brooks’s standards) 115 minutes. But the movie cannot shed his woolly energy, which puts any no-name side character at risk of dropping an impassioned soliloquy about some heretofore-unexamined personal drama.

The plot ping-pongs among Ella’s statehouse maneuverings, her personal “scandal” (the actual contents of which are relatively harmless, considering our age of daily political crises), and her off-kilter family members. At first Ella McCay seems like it might be about how this intrepid political prodigy pulls everything together, but Brooks has always been more interested in watching things unravel and then plunging into the resulting tangles. Mackey, doing spirited work, is at her best when things are at their worst. Other performances, like Lowden’s egotistical failson and Fearn’s twitchy brother, come off too broadly even for Brooks’s stylized tone.

The real juice of the movie is in the political intrigue, not the personal, and its most successful scenes revolve around Ella running headfirst into stagnant partisan realities. The 2008 setting, which initially seems baffling, ends up being a pointed reference to the last moment when idealism could triumph in America. The entire film comes off like an apology from Brooks on behalf of his generation to his kids and grandkids—a big sorry for the turmoil his once-principled cadre have dumped into their laps, Great Recession and all. It’s that stealthy sense of guilt that turns Ella McCay into a rich, if often bewildering, document for me. Yes, it’s the kind of movie Hollywood doesn’t make much of anymore, but honestly, even back in the day, the industry rarely ever pushed out something this delightfully weird.