In 1987 Keaton starred in Baby Boom, her first of four collaborations with writer-producer Nancy Meyers. She played a Manhattan career woman who is suddenly forced to care for a toddler. A modest box-office success, Keaton's performance was singled out by Kael, who described it as "a glorious comedy performance that rides over many of the inanities in this picture. Keaton is smashing: the Tiger Lady's having all this drive is played for farce and Keaton keeps you alert to every shade of pride and panic the character feels. She's an ultra-feminine executive, a wide-eyed charmer, with a breathless ditziness that may remind you of Jean Arthur in The More The Merrier." That same year Keaton made a cameo in Allen's film Radio Days as a nightclub singer. 1988's The Good Mother was a financial disappointment (according to Keaton, the film was "a Big Failure. Like, BIG failure"), and some critics panned her performance; according to The Washington Post, "her acting degenerates into hype—as if she's trying to sell an idea she can't fully believe in."
In 1987 Keaton directed and edited her first feature film, Heaven, a documentary about the possibility of an afterlife. It met with mixed critical reaction, with The New York Times likening it to "a conceit imposed on its subjects." Over the next four years Keaton directed music videos for artists such as Belinda Carlisle, including the video for Carlisle's chart-topping hit "Heaven Is a Place on Earth," two television films starring Patricia Arquette, and episodes of the series China Beach and Twin Peaks.
Keaton has continued to pursue her interest in photography. In 1987 she told Vanity Fair, "I have amassed a huge library of images—kissing scenes from movies, pictures I like. Visual things are really key for me." She has published several more collections of her own photographs and served as an editor of collections of vintage photography. Works she has edited in the last decade include a book of photographs by paparazzo Ron Galella; an anthology of reproductions of clown paintings; and a collection of photos of California's Spanish-Colonial-style houses.