38: West Side Story (1961)

Kenny Neal (Starlight Express) and Bryan Plofsky (Suessical!) join Patrick for what is certainly the most Academy Award-winning film in the Sondheim filmography: 10 Oscars, including “Best Picture” and “Best Music, Scoring of a Musical Picture” shared by 4 people (none of whom are named Bernstein or Sondheim).

Patrick Flynn

Patrick is is a Helen Hayes Award-nominated playwright & award-winning filmmaker based in Washington, D.C. Produced stage works include The Ferberizing of Coral (winner, Samuel French Off Off Broadway Short Play Festival), Tinker Bell (licensed by Dramatic Publishing), The Velveteen Rabbit (licensed by Theatrical Rights Worldwide), Giant Box of Pr0n (licensed by Next Stage Press), Sheila and Moby (Helen Hayes Recommended), Where in North Dakota is Carmen Sandiego? (Awesome Con 2018). His podcast The Original Cast was named one of Playbill’s “7 Standout Theatre Podcasts.” Web series: I Live With This (Outstanding Series & Outstanding Writing, L.A. Webfest), Long Distance Relationship (Bronze Medal, TIVA-DC Peer Awards), Keith Powell Directs a Play (starring Keith Powell and Aubrey Plaza). His films made for the 48 Hour Film Project have won over 30 awards including 9 best-of-city citations, 3 for writing, 3 for directing, and 2 Best Films. His book Visual Literacy: A Practical Text on the Analysis, History, and Creation of Visual Media is available from Kendall-Hunt. He is a professor at American University & Catholic University and a member of the Dramatists Guild.

https://UnknownPenguin.com
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39: A Funny Thing Happened on the Way to the Forum (1966)

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37: Six by Sondheim (2013)