Inline engines are still in the majority, but there are four V-8s, one a flathead in the Caddy fastback, two modern ones in the '50 Olds and '49 Cadillac with the '53 Buick the newest addition for that line. Update: Sorry, Lincoln! To the right of the Oldsmobile, you're a flathead V-8, too, with Hydra-Matic.

The black car to the far right just before the Plymouth Suburban's tail light is a very rare 1950 Chrysler eight passenger limo with its driver waiting in front for the owner to return. If it's a Windsor, it's one of 174, if a top of the line Crown Imperial on the 145.5" wheelbase, it's one of 205 and weighs 5,300 lbs.

Just a short hike from the Cliff House are the Sutro baths. For anyone who is a fan of the 1971 movie "Harold & Maude" the Sutro baths were where Harold and his Uncle Victor discussed Harold joining the military and where Maude, masquerading as a "protester" stole Harold's shrunken head and then fell through the hole when Harold grabbed her sign and chased her. Great movie and great location!

[Also featured prominently in the 1958 feature "The Lineup," based on the TV show of the same name. -tterrace]

Here's another comparison taken from nearly the same location, this time during the 2003 remodeling when the "moderne" facade was being removed to reveal the original 1909 building hidden behind the 1950s addition.

Later, missing details such as cornices and parapets were restored so the Cliff House today looks much as it did when first built in 1909.

(As a side note, San Francisco historian argue over how many Cliff Houses have been on the site. Some claim three, others as many as six. It all depends if you consider a remodeled building a "new" structure.)

[Further research seems to indicate there are only three basic structures solidly documented, so I've corrected my utterance in the comment below. -tterrace]

That fastback on the left is a 1946 or '47 Cadillac. Note the dividers in the rear window which were a feature of all Cadillac models during the '40s. The car in the foreground is a '49 DeSoto.

Down that hill, besides Playland (which is featured in the Orson Welles/Rita Hayworth film "Lady from Shanghai" there was the Musee Mecanique (now at Fisherman's Wharf) which was a paradise for a mechanically minded kid and the Camera Obscura. I used to take the F train from the top of Solano Avenue in Albany all the way across to the Key System terminal in SF, have lunch with my dad, then off to Ocean Beach for the afternoon. If you turned that car around and went back up you'd go past Louie's cafe and to the Seal Beach Inn, where Ken Kesey wrote "One Flew Over the Cuckoo's Nest." Left at the Seal Beach and you'll find yourself at the USS San Francisco monument and an old Nike base. Fascinating corner of a fascinating city.

I think that the sleek blue fastback is a 1946 or '47 Cadillac. Note the vertical taillights, as well the trim bars in the back window. Also, the '46-'47 Cadillacs appeared somewhat wider in the rear than their '48-'49 successors, as they had more bulbous back fenders.

Would that be this one?

[Yes. Today's Cliff House, the same one on the photo, is the fifth third built on the site, restored to its original 1909 appearance. -tterrace]

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I think the blue beauty is a 1949 Olds. Chevy, Olds, Buick and Caddie had the same fastback models, the Olds, Buick and caddie with fancier chrome and tail lights. This body style was used '49 to '52. The '49 had the simpler trunk handle. My '50 Chevy FB was my favorite ride.

Thanks for sharing this great photo. It's before my time in SF but it sure makes me wish I'd come here a couple of decades sooner.

looks to be a Buick Roadmaster Sedanette, possibly a 1949.

Here's a different view of the same restaurant, taken a few years later. Some of the same cars were probably in the parking lot in both pictures!

https://www.shorpy.com/node/13472

In 1955 we lived in the Sunset District of San Francisco. Two blocks from Ocean Beach, a few blocks from Playland at the Beach, Golden Gate Park and the Cliff House was up the hill from us along the Great Highway. A great time to be a young lad in San Francisco.

Any ideas on the blue beauty, 4th from the left, pointing west. What a time.

Parking places sure have gotten a lot narrower than they were in 1955.