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Born in San Francisco and showing promise in performing at an early age, Grady was awarded scholarships for acting classes at American Conservatory Theatre's Young Conservatory, and began training in the full-time program with San Francisco Ballet, for which he was awarded a full scholarship. He was born to entertainer parents: his mother Julie Lawler is a singer/actress who trained with the American Academy of Dramatic Arts in New York and fronted the punk rock band "The Urge" (opening for Devo, Blondie and the Go-Go's) and his father Michael Grady began his career performing in the Lincoln Center Theater revival of "Showboat" (starring Barbara Cook and Margaret Hamilton), and later trained under George Balanchine at New York City Ballet. Sean's first role outside of school was as Wally Webb/Si Cowell in "Our Town" (with former Miss America Lee Meriwether in the role of the Stage Manager). At the same time, Sean joined the San Francisco Bay Area Puppeteers Guild, and worked with mentors Lee Armstrong, Kamela Portuges, Randal Metz and Lewis Mahlmann; he traveled on a full scholarship to train with the Puppeteers of America at U.C. San Diego for their Summer Puppetry Convention. He attended San Mateo High School, joining prestigious alumni Alicia Silverstone and Barry Bostwick. He began performing professionally in the San Francisco Bay Area, most notably in several productions with American Musical Theatre of San Jose (including "On The Twentieth Century" with Jo Anne Worley) and earned his membership into Actors' Equity Association. He applied for and was accepted to the American Musical and Dramatic Academy in New York City, where he studied in their two-year program. Upon graduation, Grady performed in New York, in regional theatre and in film (living in both Los Angeles and New York City) and later attended Chicago's Second City. In 2010, Grady co-created and co-wrote a TV Pilot and Concept, "Preston and Jerry", which was selected by Lifetime into their development offices.