What do John C. Reilly and Taylor Swift have in common? The Great American Songbook

John C. Reilly joins to discuss Mr. Romantic, his theatrical tribute to the Great American Songbook that treats Irving Berlin and Tom Waits as equals in the canon of timeless American song. Reilly recorded live in one room with his band using vintage ribbon microphones, embracing the squeaks and imperfections while layering in cinematic sound effects—crickets outside a lover's window, a collect call from prison—to transform each standard into an immersive scene. But what makes a song from the 1920s feel eternal? Music data scientist Chris Della Riva, author of the forthcoming Uncharted Territory and the newsletter Can't Get Much Higher, breaks down how composers like the Gershwins wrote for amateur musicians playing sheet music at home, creating universal lyrics and AABA structures where the hook comes first. That accessibility is precisely what draws Reilly to this repertoire. He sees himself in the lineage of interpreters like Sinatra, not selling his own story but passing along music that already belongs to all of us, like holding up a seashell and saying, "Isn't this one beautiful?"

Songs Discussed

• Taylor Swift "The Last Great American Dynasty"
• George Gershwin "I Got Rhythm"
• Village People "Y.M.C.A."
• Billie Eilish "Bad Guy"
• Frank Sinatra "On the Sunny Side of the Street"
• Judy Garland "Over the Rainbow"
• Ella Fitzgerald "My Romance"
• George Gershwin "But Not for Me"
• Elvis Presley "Are You Lonesome Tonight"
• The Beatles "We Can Work It Out"
• The Beatles "Get Back"
• The Beatles "Yesterday"
• John C. Reilly "Moonlight Serenade"
• John C. Reilly "Dreams"
• John C. Reilly "Johnsburg, Illinois"
• John C. Reilly "Falling in Love Again"
• John C. Reilly "What'll I Do"
• John C. Reilly "Picture in a Frame"
• John C. Reilly "Just Another Sucker on the Vine"
• Randy Newman "Ragtime"
• John C. Reilly & David Garza "What's Not To Love"
• Harry Nilsson "Coconut"
• Judy Garland "Somewhere Over the Rainbow"
• Dooley Wilson "As Time Goes By"
• The New Vaudeville Band "Winchester Cathedral"
• Andy Williams "The Days of Wine and Roses"
• Nat King Cole "The Frim Fram Sauce"

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