Francis Albert Sinatra (/sɪˈnɑːtrə/; December 12, 1915 – May 14, 1998) was an American singer and actor. Nicknamed the "Chairman of the Board" and "Ol' Blue Eyes", he is regarded as one of the most popular entertainers of the 20th century. Sinatra is among the world's best-selling music artists, with an estimated 150 million record sales globally.

Born to Italian immigrants in Hoboken, New Jersey, Sinatra began his musical career in the swing era and was influenced by the easy-listening vocal style of Bing Crosby. He joined the Harry James band as the vocalist in 1939 before finding success as a solo artist after signing with Columbia Records four years later, becoming the idol of the "bobby soxers". In 1946, Sinatra released his debut album, The Voice of Frank Sinatra. He then signed with Capitol Records and released several albums with arrangements by Nelson Riddle, notably In the Wee Small Hours (1955) and Songs for Swingin' Lovers! (1956). In 1960, Sinatra left Capitol Records to start his own record label, Reprise Records, releasing a string of successful albums. He collaborated with Count Basie on Sinatra-Basie: An Historic Musical First (1962) and It Might as Well Be Swing (1964). In 1965, he recorded September of My Years and starred in the Emmy-winning television special Frank Sinatra: A Man and His Music. After releasing Sinatra at the Sands the following year, Sinatra recorded one of his most famous collaborations with Tom Jobim, Francis Albert Sinatra & Antonio Carlos Jobim. It was followed by 1968's Francis A. & Edward K. with Duke Ellington. Sinatra retired in 1971 following the release of "My Way" but came out of retirement two years later. He recorded several albums and released "New York, New York" in 1980.

Sinatra also forged a highly successful acting career. After winning the Academy Award for Best Supporting Actor for From Here to Eternity (1953), he starred in The Man with the Golden Arm (1955) and The Manchurian Candidate (1962). Sinatra also appeared in musicals such as On the Town (1949); Guys and Dolls (1955); High Society (1956); and Pal Joey (1957), the last of which won him a Golden Globe Award. Toward the end of his career, Sinatra frequently played detectives, including the title character in Tony Rome (1967) and the titular The Detective (1968). He received the Golden Globe Cecil B. DeMille Award in 1971. Sinatra also directed a single film in his career, the anti-war drama None but the Brave (1965). On television, The Frank Sinatra Show began on CBS in 1950, and Sinatra continued to make appearances on television throughout the 1950s and 1960s.

Sinatra was recognized at the Kennedy Center Honors in 1983, awarded the Presidential Medal of Freedom in 1985, and received the Congressional Gold Medal in 1997. He earned 11 Grammy Awards, including the Grammy Trustees Award, Grammy Legend Award, and the Grammy Lifetime Achievement Award. American music critic Robert Christgau called Sinatra "the greatest singer of the 20th century" and he continues to be regarded as an iconic figure.

"They'd fought through his childhood and continued to do so until her dying day. But I believe that to counter her steel will he'd developed his own. To prove her wrong when she belittled his choice of career ... Their friction first had shaped him; that, I think, had remained to the end and a litmus test of the grit in his bones. It helped keep him at the top of his game."

Francis Albert Sinatra was born on December 12, 1915, in a tenement at 415 Monroe Street in Hoboken, New Jersey, the only child of Italian immigrants Natalina "Dolly" Garaventa and Antonino Martino "Marty" Sinatra. Sinatra weighed 13.5 pounds (6.1 kg) at birth and had to be delivered with the aid of forceps, which caused severe scarring to his left cheek, neck, and left ear, and perforated his eardrum—which remained damaged for his whole life. Sinatra's grandmother resuscitated him by running him under cold water until he gasped. Because of Sinatra's injuries, his baptism at St. Francis Church in Hoboken was delayed until April 2, 1916. A childhood operation on Sinatra's mastoid bone left major scarring on his neck, and during adolescence, Sinatra was further scarred by cystic acne. He was raised in the Roman Catholic Church.

Sinatra's mother, Dolly, was energetic and driven; biographers believe that she was the dominant factor in the development of her son's personality and self-confidence. Sinatra's fourth wife, Barbara, would later claim that Dolly "knocked him around a lot" when he was a child. Dolly became influential in Hoboken and in local Democratic Party circles. She worked as a midwife, and according to Sinatra biographer Kitty Kelley, ran an illegal abortion service that catered to Italian Catholic girls, for which she was nicknamed "Hatpin Dolly". She had a gift for languages and served as a local interpreter.

Sinatra's illiterate father, Marty, was a bantamweight boxer who later worked at the Hoboken Fire Department, working his way up to captain. Due to his illiteracy, Marty stressed the importance of a "complete and full" education and had instilled in his son the desire to become a civil engineer and enroll at Stevens Institute of Technology in Hoboken. Sinatra spent much time at his parents' tavern in Hoboken, working on his homework and occasionally singing for spare change. During the Great Depression, Dolly provided money to her son for outings with friends and to buy expensive clothes, resulting in neighbors describing him as the "best-dressed kid in the neighborhood". Excessively thin and small as a child and young man, Sinatra's skinny frame later became a staple of jokes during stage shows.