San Diego Hysterical Society

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Second Oscar's Drive-in Opens

by Velma Talmadge

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The rousing success of the first Oscar's Drive-in on Harbor Drive prompted owner Oscar Soledad to open a second location on what is now El Cajon Blvd.

Rocky and Oscar Jr.
- Soledad & Ashley at Opening -

Soledad and his long time friend Stephen Ashley both shared passions for fast cars, fast food, and fast waitresses. Thus was born drive-in restaurants with hamburgers served by women on roller skates.

Soledad stole his idea of a drive-in from the Jonathon Ashley drive-thru bakery on Point Loma, but later made son Stephen Ashley a partner (in order to avoid a lawsuit).

While many automobile pink slips were exchanged on El Cajon Blvd. as a result of impromptu races, Stephen lost the pink slip to his 1909 Bugatti ╔spešial in a bet over where the cheese was located in Oscar's "triple-deck" burger. Stephen bet it was on the top of the top patty. He lost. The cheese was always on the bottom of the bottom patty.


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