Truman Cox and Derek Palmer opened the video lounge in southeast Portland's Buckman neighborhood in June 2022, near another LGBTQ establishment named Crush Bar.

[2] According to Eater Portland's Brooke Jackson-Glidden, the interior paid homage to Barracuda Lounge, which she described as "a classic New York drag bar".

Sissy Bar had a similar backbar and long banquette,[1] as well as illuminated cubes, which Willamette Week's Andrew Jankowski compared to panels on Simon.

[3] Walls displayed photographs of "gay divas", such as Paris Hilton, Jennifer Lopez, Madonna, and Dolly Parton.

[1][7] The nachos had Juanita's tortilla chips with cheese, jalapeño, sour cream, and tomato, and the avocado salad had guacamole with cucumber, lime, and scallion.

[5] Among events the bar has hosted are Ingenue, a lesbian dance party by DJ Lavender Menace's, and Shape of Drag, described as a "high concept" show by Silhouette.