Frank Sinatra Frank Sinatra was an American singer who is one of the most highly acclaimed male popular song vocalists of all time. Renowned for his impeccable phrasing and timing, many critics place him alongside artists such as Bing Crosby, Elvis Presley and the Beatles as one of the most important popular and influential music figures of the 20th Century. Sinatra launched a second career as a dramatic film actor, and became admired for a screen persona distinctly tougher than his smooth singing style. Sinatra also had a larger-than-life presence in the public eye, and as "The Chairman of the Board" became an American icon, known for his brash, sometimes swaggering attitude, as embodied by his signature song "My Way".