Ray Bolger’s 1949 Tony Award for WHERE'S CHARLEY? Up for Auction

From Broadway’s golden age to Hollywood’s silver screen, RR Auction’s latest sale spotlights the legends who defined entertainment history. Among the treasures in the Classic Entertainment section of the firm’s November Fine Autographs and Artifacts auction is a rare piece of theatrical history: the Tony Award presented to Ray Bolger for Where’s Charley?—a milestone in both the performer’s storied career and the early years of the American Theatre Wing’s celebrated honors.

Presented to Ray Bolger for his 1948–49 performance as Charley Wykeham in Where’s Charley?, this original American Theatre Wing Antoinette Perry Award—better known as the Tony—was part of the 3rd Annual Tony Awards, held April 24, 1949, at New York’s Waldorf-Astoria Grand Ballroom. Measuring three inches in diameter and struck in sterling silver, the medallion bears raised dramatic masks on the front and an engraved dedication on the reverse: “The American Theatre Wing Presents to Ray Bolger This Award for His Performance in Where’s Charley 1948–49.”

Accompanied by an original Playbill for the St. James Theatre production, a custom presentation case, and a letter of authenticity from Bolger’s niece, Ruth Ann Rickard, the award remains in mint condition, showing only light tarnish from age.

Best remembered as the lovable Scarecrow in The Wizard of Oz, Bolger brought his trademark charm and elasticity to Where’s Charley?, turning the song “Once in Love with Amy” into a cultural phenomenon that stopped the show nightly—and even prompted audiences to sing along. He later reprised his role in the 1952 Warner Bros. film adaptation, cementing his reputation as one of Broadway’s most beloved leading men.