Ole Madrid opened in 1990, before San Diego's downtown was known to be a local hot spot. At this time, Horton Plaza just opened and there were few restaurants in the area. Taking the risk that people would overcome their fear of downtown, the owners began what would eventually become the soul of the Gaslamp Quarter. Soon after opening in a small location on F street (now The Start of India), Ole Madrid's unique style became an instant hit. A vacant movie theater on Fifth Avenue provided to be the perfect site.