Mama's Boy (2007)

Mama’s Boy is the kind of offbeat, oddly tender comedy-drama that sneaks up on you: it takes a ridiculous premise—a grown man treating his mother’s love life like a hostile takeover—and plays it with enough sincerity that the laughs have a sting of truth. Jon Heder leans into Jeffrey’s arrested development with just the right mix of cluelessness and vulnerability, while Diane Keaton gives the movie its warm, lived-in heartbeat, and Jeff Daniels is a delight as the relentlessly upbeat “guru” who might be exactly what this household needs. The vibe is quirky and slightly mean in that early-2000s indie way, but it’s punctuated by genuinely amusing set pieces and welcome spark from the supporting players, including an always-watchable Anna Faris. It won’t be for everyone—its humor can be broad and its protagonist can be hard to root for—but if you like messy, character-driven comedies about growing up late, it’s an easy, curious watch.

Mama’s Boy is clearly trying to be an offbeat, slightly dark rom-com about an overgrown man-child forced to grow up when his mom finally chooses herself, and on paper that’s a workable setup. The problem is the comedy often lands with a thud and the pacing feels messy, so what should be cringe-funny can come off grating and oddly predictable instead. Jon Heder leans hard into the awkwardness, which will either be your exact flavor or the reason you bail early, while Diane Keaton and Jeff Daniels do what they can to give the material some charm. If you like uncomfortable, petty “war” comedies with a cynical streak and don’t need many actual laughs per minute, you might get through it; if you’re hoping for a sharp, warm crowd-pleaser, this isn’t the one.