Mermaids went through three directors and two Charlottes before it finally reached the screen. Lasse Hallström was announced in early 1989, then left to make Once Around. Frank Oz replaced him and departed after reported clashes with the leads. Richard Benjamin, the actor turned director behind My Favorite Year, took over as shooting began. Emily Lloyd had already filmed scenes as Charlotte before Winona Ryder replaced her, and producer Patrick Palmer later said the earlier directors had pushed for something darker, similar to Patty Dann’s original novel. Benjamin went for warmth instead, and that decision gives the finished movie its personality.

It is 1963, and Rachel Flax (Cher, The Witches of Eastwick) solves romantic disappointment by moving. Her latest reset takes daughters Charlotte (Ryder, Beetlejuice) and Kate (Christina Ricci, Cursed, in her screen debut) to Eastport, Massachusetts. Charlotte is Jewish, fascinated by Catholic saints, and convinced she is destined for a convent until she meets Joe (Michael Schoeffling, Sixteen Candles), the young caretaker up the hill. Kate mostly wants to swim. Rachel, meanwhile, catches the eye of Lou Landsky (Bob Hoskins, Who Framed Roger Rabbit), a shoe-store owner who looks like he might actually stay put.

Cher reportedly modeled parts of Rachel on her mother, Georgia Holt, and costume designer Marit Allen even borrowed from Holt’s closet. The movie, though, belongs just as much to Ryder. Her narration turns Charlotte’s guilt, religious obsession, and teenage melodrama into comedy without making fun of her, and the performance earned Ryder a National Board of Review supporting-actress prize and her first Golden Globe nomination. The late Hoskins makes Lou both funny and reassuring, while Ricci gives Kate enough spark to keep the youngest Flax from becoming a cute prop. Schoeffling is, well, dreamboat is the first word that comes to mind.

The coming-of-age beats are familiar, and not every tonal turn lands, which helps explain the mixed reviews at release. Still, the movie has aged into a charming snapshot of several careers at interesting moments: Cher after Moonstruck, Ryder in the middle of a major run, and Ricci just getting started. I find it an easy, enduringly funny film to return to often. Strong preview response pushed Orion to move the film up to a wide December 1990 opening, and it eventually earned about $35 million. For a shorter take, an earlier look at the film ran here in 2013.