Headley got his start in 1930, as an apprentice to popular jeweler Paul Flato, who is considered the first celebrity jeweler, where he worked alongside Count Fulco di Verdura.
In addition to 5 non-appearing film credits, Flato had an on-screen role as a jeweler in the 1940 film Hired Wife starring Rosalind Russell and Virginia Bruce.
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Flato was convicted in 1943 of fraudulently pawning $100,000 in jewels that colleagues and clients had entrusted to him, and served 16 months in Sing Sing Penitentiary.
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