Jolly Joan sandwich shop (It's slogan: "Where you eat best for less") was reportedly the largest restaurant in the state, and in business from the 1930s through the 1960s. Festooned with a big neon sign, it was located Downtown on SW Broadway, near Washington.
Top of the Cosmo was a restaurant and bar at the top of a hotel that is now the Red Lion in the Lloyd District. Richard Engman, who heads Oregon Rediviva, a public history research and writing company, writes on his blog:
"In December 1962, the Cosmopolitan Motor Hotel opened at the corner of NE Grand Avenue and Holladay Street, plonked sort of halfway between the new Lloyd Center shopping mall and the new Veterans Memorial Coliseum. Though only a modest five floors in height, it boasted a rooftop dining room touted as "Top of the Cosmo," headed by a Swiss-born chef, Ernest Herzog. Herzog had experience in Puerto Rico and at the Portland Sheraton (another new hotel, located at Lloyd Center) before coming to the Cosmo, where his menus featured "Oregon grown fresh chicken" in 1963.
By 1964, Herzog and the Cosmo were advertising a menu that went "Around the World in Seven Days." (Herzog) went on to head his own restaurant, the Swiss-themed Matterhorn in the 1970s"
Reed Darmon says, "The places are even older than me but I did go to the Top of the Cosmo, to its bar called the Agate Lounge. The tabletops were made out of cut agates that had lights shining through them. It also had a rooftop swimming pool for hotel guests."