Playland evolved from earlier amusement concessions along Ocean Beach that dated to the early 1900s. George K. Whitney consolidated the various rides and attractions into a unified park beginning in the late 1920s. By the 1930s, Playland-at-the-Beach, also known as Whitney's Playland, was a full-fledged amusement park featuring the Big Dipper wooden roller coaster, a funhouse, bumper cars, a shooting gallery, and food stands selling the park's famous It's-It ice cream sandwiches. The park sat directly on the beach, exposed to the fog and wind that rolled in from the Pacific. The weather was part of the charm: Playland was never a sunny, sanitized experience. It was gritty, salty, and loud.

By the 1960s, Playland was showing its age. The wooden structures required constant maintenance, and the park's operations were increasingly expensive. Safety concerns about the aging rides, combined with the rising value of the beachfront land, made closure inevitable. Playland closed in September 1972 and was demolished. The land was eventually developed into condominiums. The Big Dipper, which had thrilled riders since 1922, was torn apart. Some artifacts were preserved by collectors, and Laughing Sal was eventually displayed at the Musee Mecanique, first at the Cliff House and later at Fisherman's Wharf, where she continues cackling at new generations.

Playland exists now only in photographs, artifacts, and the memories of San Franciscans old enough to have ridden the Big Dipper. The It's-It ice cream sandwich, created at Playland in 1928, survived the park's demolition and is still sold throughout the Bay Area, one of the few edible monuments to a lost landmark. The stretch of the Great Highway where Playland once stood is residential now, the condominiums facing the same ocean that the park's visitors watched while eating cotton candy and dodging seagulls. The fog still rolls in. The ocean still crashes. Laughing Sal still laughs, though now behind glass in a different part of the city.