[4] A writer for the San Francisco Chronicle in 1922 reported that “by 1921 the owners had spent $150,000 to produce ten spectacular new rides ("clean, safe, moral attractions") which were open from noon to midnight, everyday.” [7] Attractions included Arthur Looff’s Bob Sled Dipper roller coaster, also known as "the Bobs" (1921), the Looff-designed Big Dipper roller coaster (1922), Shoot-the-Chutes, the carousel, Aeroplane Swing, the Whip, Dodg 'Em, the Ship of Joy, the Ferris wheel, Noah’s Ark, and almost a hundred concessionaires.

[4] The Whitney brothers opened a photographic concession that year, pioneering a fast photo-finishing process that allowed people to take pictures home rather than having to wait days for the film to be developed and images printed.

In 1937, George Whitney Sr. purchased the then-vacant Cliff House from the Sutro estate and reopened it as an upscale roadhouse that same year.

[10] George Whitney was called “The Barnum of the Golden Gate” as he went on to buy up the concessions and even bought the Sutro Baths in 1952.

[4] Despite this expansion, the post-war years saw the tearing down of the Shoot the Chutes in 1950 and the Big Dipper in 1955, and after George Whitney died in 1958, Playland was never quite the same.

Another favorite was the Diving Bell, a metal chamber that took guests under water and then returned them to the surface with a big splash.

San Francisco bought the carousel in 1998, and it is now located off Fourth Street downtown in Yerba Buena Gardens.

Next, patrons squeezed through the spin-dryers and entered the main area of the Fun House, which contained a Joy Wheel (flat wooden disc that spun quickly and forced kids to slide off), the Barrel of Laughs (rotating walk-through wooden barrel), the Moving Bridges (connected gang planks that went up and down), and the Rocking Horses (attached by strong springs to a moving platform creating quite a galloping sensation).

[15] Also referred to as Giant Camera by a sign on the south side of the camera-shaped building,[16] Camera Obscura and Holograph Gallery (sign above entrance)[17] was added to the National Register of Historic Places (locally) in 2001 for its engineering significance, "since it retains its original projection table, lens, and mirror and continues to operate in the same manner as it did in 1946.

"[15] In 1929, George Whitney relocated Topsy's Roost, a popular restaurant specializing in chicken, which had been established two years previously at the south end of the esplanade.

[19][20] Driving south along the beach on the Great Highway from the Cliff House, the first building you came to was Topsy’s Roost, which became more than just a chicken dinner house—it was also a popular nightclub.

The restaurant was named for Topsy, a character in Harriet Beecher Stowe's Uncle Tom's Cabin and its decor depicted Negro stereotypes.

[10] The Topsy's Roost building later became the site of the Edgewater Ballroom, a slot car raceway, the second home of Chet Helm's Family Dog Productions, and lastly, the Friends and Relations Hall.

[19][9] In 1947, Skateland, a roller rink, was built on an empty lot where an annex of the Ocean Beach Pavilion once stood.