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Originally from "Soprano" turf in New Jersey, Olana is the daughter of famed jazz accordionist Orlando DiGirolamo (Lanny DiJay), who recorded with Charles Mingus and Teo Macero. She started writing and performing stand-up comedy in New York City after graduating from School of Visual Arts and studying improv at Chicago City Limits. After moving to Los Angeles, she became a writer/producer at Warner Bros. and Capitol Records working with artists including Madonna, Bette Midler, Prince, Frank Sinatra, Adam Sandler, Howard Stern, Cher, Beastie Boys, Paul McCartney and Katy Perry. Olana is directing her first feature-length documentary film, Play That, Teo, about the life and work of legendary Columbia Records producer Teo Macero.