Popular with young adults, the restaurant was known for serving fishbowl alcoholic beverages, for its 1950s furnishings, and for hosting karaoke, trivia competitions, and goldfish racing tournaments.

The restaurant is said to have influenced local alcohol policies; noise complaints and signs of drunken behavior by patrons made the business a target for curfews and closure.

[1][3] In 1963, The Oregonian described the artwork on the interior walls, which included a large and colorful painting depicting a gypsy camp, and an "attractive" nude called Dian by Grace Harlow, a painter and former student of Louis Bunce.

[9] An obituary published by The Oregonian in 1987 said that Gertrude "Tiny" Hursick of Lake Oswego co-owned Gypsy and Gordon's 7-Up Bar, also located in Northwest Portland.

The company has owned other Portland establishments such as Bar 71,[12] Barracuda Nightclub,[13] Dixie Tavern, Grand Central Bowl, the Lotus Cardroom and Cafe, Quest,[12] and the Thirsty Lion.

[2] In 1994, city commissioner Charlie Hales and mayor Vera Katz sought to close the Gypsy due to repeated reports of assaults, public intoxication, and noise complaints.

[2][20] Its website and social media pages were shut down immediately, and a sign was posted at the club noting that Concept Entertainment had decided to sell.

[22] In 2000, Gypsy hosted opening and closing night parties for Sensory Perceptions' annual film festival, which spanned two weekends at neighboring Cinema 21.

One Oregonian contributor called Gypsy a "fitting setting" for the celebration, given its lava lamps and blue and orange fishbowl drinks, which he said were "like Pop art through a straw".

In her review, Desiree Andrews wrote that the fried artichoke hearts and pub chips were forgettable and recommended the black bean quesadilla.