At the Gazette, we have a keen interest in and commitment to preserving County history. Today’s editorial explores Frank Sinatra’s two performances at The Regent Theatre on Picton Main Street. 

Frank played the Regent twice, but nobody seems to remember either performance. There is reason to believe that Sinatra historians have suppressed his visits to the County.

The first time was in early 1950, one of Sinatra’s lowest career points. The appearance had been booked long before, intended to promote what is surely his worst film, made only for contractual reasons, The Kissing Bandit (1948). The soprano lead, Kathryn Grayson, with whom Sinatra had made several previous (and successful) films, must have had better lawyers than Frank, for she had got out of this doomed promotional tour.

Frank’s reputation had been taking a beating; the rumours of his adultery with Ava Gardner were making their way to media attention, and, reflecting the stress of his celebrity existence, Sinatra’s voice was just weeks away from the on-stage vocal hemorrhage that would alter his career and singing style forever.

Apart from one small anticipatory notice, there is no evidence that the Gazette, or any other newspaper, covered this appearance, which was originally intended to feature Sinatra and Grayson singing songs from the film before a screening. With Grayson absent, it is said that Sinatra sang his feature “Siesta” and “If I Steal a Kiss,” but refused to wear the cowboy costume from the film.

Thirty years later, there is another significant, and also undocumented, Sinatra appearance at Picton’s Regent Theatre.

In January of 1981, Frank Sinatra performed at a Regent show featuring the Buddy Rich big band. Frank had had a long history with Buddy, including a famous fistfight in the late 1940s, but by this time they had appeared together regularly, with Rich’s band accompanying Sinatra, playing the well-known Nelson Riddle arrangements from Sinatra’s greatest recordings, in exchange for a half-hour featuring Rich’s own music.

At this time, Sinatra was riding high with his last great hit, “New York, New York” (1980). He was selling out stadiums and arenas. Why would he come to Picton, and without top billing — or, indeed, any billing?

The appearance in Picton is recognized by Sinatra historians as the only time that Frank ever allegedly performed in public his version of the Sex Pistols’ “Anarchy in the U.K.” Frank had recorded this song shortly before, but never approved its release. It was his response to Sid Vicious’s 1979 travesty of Frank’s 1969 hit, “My Way.” 

Frank knew the best revenge was living well, and so he responded with taste. Nelson Riddle came out of retirement and scored it to a lightly swinging beat, a bit slower than the original. It opens with optimistic flutes, and features great syncopation in the vocal emphasis on the 2nd and 4th beats, with a stop-time figure at the close of the chorus: “I want to be” (2, 3, 4—stop) … “an-ar-chy.”

Nobody knows why Frank refused to release the recording. Some have speculated that Buddy Rich dared him to perform it at least once. Did Sinatra look at Rich’s tour schedule and realize that Picton was sufficiently close to New York State, and sufficiently obscure, that he might settle without fanfare of any kind this debt of honour? Nobody knows.

The audience that cold County night was small. Who would venture out in the depth of winter to hear a jazz band? Who among the audience stayed long enough to bear witness to this unexpected appearance of the Voice of the Century, singing unprecedented material? 

The Gazette seeks any recollections, even the foggiest, from those who may have been at either of Sinatra’s Regent appearances.