Here's how singer/actor Frank Sinatra earned his most famous nickname "Chairman of the Board." Frank Sinatra is one of the few stars to have a huge career as both a musician and an actor, which he balanced side by side. After early successes as a recording artist, Sinatra became a film star thanks to a supporting role in 1953 war drama From Here To Eternity, which earned him an Academy Award nomination. From there he would balance crowdpleasers like 1955's Guys And Dolls with acclaimed dramatic turns in The Man With The Golden Arm or classic thriller The Manchurian Candidate.
In 1965 Frank Sinatra directed his only movie None But The Brave, a gritty war drama that also marked the first American/Japanese co-production, with Warner Bros handling the American release while Toto distributed the movie in Japan. He also appeared in numerous projects with his Rat Pack buddies Sammy Davis Jr. and Dean Martin in movies like Ocean's 11 and Robin And The 7 Hoods. He largely retired from acting during the 1970s, with 1984's Cannonball Run II marking his final movie appearance.
Frank Sinatra had an equally prolific singing career and recorded many classic songs, including "Something Stupid," "Strangers In The Night" and "My Way." Sinatra continued to sing long after his acting retirement too, and in addition to solo shows, he performed with the likes of Dean Martin, Liza Minnelli and his son Frank Sinatra Jr all the way up to his retirement in 1995. One of Frank Sinatra's most famous nicknames was the "Chairman of the Board," which is closely related to his singing career.
In 1960 Frank Sinatra would found label Reprise Records after he moved away from Capital Records. Sinatra founded Reprise because he wanted more creative freedom, which is something he also offered to acts who joined the label, which included The Kinks, Rosemary Clooney and pals like Sammy Davis, Jr. It was in founding Reprise that Frank Sinatra earned the "Chairman of the Board" moniker, which soon became his most popular nickname.
Despite this, Frank Sinatra's spouse Barbara once stated the singer himself hated the term. Fans of the singer may not realize that Sinatra was once in line to play the lead in Die Hard, though he never seriously considered it. This goes back to his appearance in 1968's The Detective, which was based on a novel by Roderick Thorp. Over a decade later, Thorp published sequel Nothing Lasts Forever, which found protagonist Joe Leland trapped in a skyscraper with terrorists who have kidnapped his daughter. The book would form the basis for Die Hard, but Frank Sinatra had to contractually be offered the role first. The singer was retired from acting by this time and quickly passed.