Sinatra, Under His Skin

When does idolization cross over into obsession? Cary Hoffman, a shy Jewish kid growing up in postwar Queens, admired Frank Sinatra so much that he dreamed of becoming the singer himself. In Hoffman’s thought-provoking one-man show, “My Sinatra,” now playing Off-Broadway with musical direction by Alex Nelson, the performer interweaves the story of his infatuation with the singing of two dozen of the singer’s standards. His voice is so uncannily similar to Sinatra’s that few can tell them apart.

Hoffman, who is an executive producer of the TNT series “Men of a Certain Age,” starring Ray Romano, has had a varied and extremely successful career in the music industry. He has written two Top 20 country hits, composed well-known advertising jingles, co-written (with Ira Gasman) a hit Off-Broadway revue called “What’s a Nice Country Like You Doing in a State Like This?” and managed the career of R&B singer Luther Vandross.

“My Sinatra” is a reworked version of a show that Hoffman has performed for the last eight years all over the country, including a run at the Triad Theatre here, and recorded for a 2009 PBS special that was viewed by more than two million people.

“It’s a pathetic story of someone trying to be someone else his entire life,” the self-deprecating performer told The Jewish Week, explaining that Sinatra became a father figure for him after his real father and grandmother were killed in a car crash when Hoffman was seven years old. “It was my search for Dad; I wanted to be in his world, because it was so much better than my world.” He started by doing a Victor Borge show in Florida, but soon decided that it was Sinatra whom he most wanted to imitate.

Hoffman called Sinatra, who died in 1998, the “coolest guy who ever lived. His toughness and tenderness epitomized New York and his music, as someone once said, was the soundtrack of America.” Hoffman, who had three uncles who were musicians, made his “singing debut” at his bar mitzvah. “I thought that I was at the Sands Hotel. I did a Sinatra version of the Haftarah and I got the only standing ovation in the history of the Kew Gardens Hills Jewish Center.”

Sinatra did have strong ties to the Jewish community. The entertainer, who wore a small mezuzah around his neck (a gift from an elderly Jewish neighbor who looked after him during his boyhood in Hoboken), sang at an “Action for Palestine” rally in 1947, helped smuggle money to the Haganah for arms purchases during the War of Independence and funded the student center at the Hebrew University in Jerusalem — the site of the 2002 terrorist bombing that claimed nine lives. He also played a Jewish pilot opposite Kirk Douglas in the 1966 film “Cast a Giant Shadow,” filmed in Israel, in which Sinatra’s character improbably dive-bombs Egyptian tanks with seltzer bottles.

As Anthony Summers and Robbyn Swan point out in their comprehensive recent biography, “Sinatra: The Life” (Knopf, 2005), millions of immigrants and their children were inspired by Sinatra’s proud assertion of ethnicity and his refusal to countenance bigotry of any kind. But while Sinatra’s fans are legion, Hoffman insists that he can differentiate the Italians from the Jews in his audience simply by requesting them to snap their fingers. “The Italians make a loud click. The Jews make a dull thud. Could it be the olive oil?”

“My Sinatra” runs through Labor Day at the Midtown Theatre at the Ha! Comedy Club, 163 W. 46th St. Performances are Saturdays at 2:30 p.m. and 7:30 p.m., Sundays at 5:30 p.m., and Mondays at 7:30 p.m. For tickets, $55, call OvationTix at (866) 811-4111 or visit www.mySinatra.com.