Dorsey’s theme song was “I’m Getting Sentimental Over You.” But Dorsey was anything but sentimental in matters of money. When Sinatra went out on his own, Dorsey forced him to sign a punitive contract that would grant Dorsey a percentage of all of the singer’s future royalties. Sinatra thought it worth the risk. Later he managed to slide out of the contract altogether, though it cost him a considerable amount of money and more. It resulted in a terminal fallingout between bandleader and singer. “I hope you fall on your ass,” Dorsey told the singer. Dorsey wanted Sinatra to fail, and Sinatra never fully forgave him, though he did turn up unannounced to toast the bandleader and sing at a memorable Dorsey tribute in New York in February 1955. (If you can find the CD called This One’s for Tommy , featuring Sinatra and Jo Stafford, buy it.) Years later—June 1979, in Los Angeles—Sinatra introduced Harry James to a live audience: James was a great guy. James had let him out of his contract after only six months. “And then there was Tommy Dorsey,” Sinatra said. “And when I wanted to get out of my contract to him, it cost me seven million dollars.” Suddenly the specter of Tommy Dorsey materialized before him as a ghost to a Shakespearean prince. “You hear me, Tommy? You hear me? I’m talking to you.”


Sinatra’s favorite toast: “May you live to be a hundred, and may the last voice you hear be mine.”

In The Godfather (1972), Michael Corleone (Al Pacino) explains to his girlfriend Kay Adams (Diane Keaton) how his father had liberated the famous singer Johnny Fontane (Al Martino) from the punitive contract a bandleader had made him sign as a precondition for allowing him to leave the band. “My father made him an offer he couldn’t refuse,” Michael says. “Luca Brazzi held a gun to his forehead and my father assured him that either his brains or his signature would be on this sheet of paper.” Because of The Godfather , many people believe (erroneously) that Sinatra landed the part of Maggio in From Here to Eternity —his comeback part, which saved his career—because a Mafia boss dispatched a thug to decapitate a stallion and put the bleeding head in the resistant film director’s bed while he slept.

Of how many songs is it true that Sinatra’s version is definitive? Of “I’ve Got You Under My Skin,” certainly, where Sinatra’s perfectionism required 22 takes on January 12, 1956. Many fans (I am one) think this the greatest of Sinatra’s finger-snapping up-tempo songs, with a wondrous instrumental bridge featuring Milt Bernhart’s inspired trombone riff. It was true of “Saturday Night Is the Loneliest Night of the Week” during World War II, of “Witchcraft” in the late 1950s, of the incomparable saloon songs “One for My Baby (and One More for the Road)” and “I’m a Fool to Want You,” and of nearly all the “all” songs that Sinatra turned into standards: “All or Nothing at All,” with the Harry James band, which sold 8,000 copies when first released in 1939 and a million when rereleased years later; “All the Things You Are,” on the Columbia label in 1943, with its climactic mile-high last note; “It All Depends on You,” as arranged by George Siravo in 1949; “All of Me,” as arranged by Nelson Riddle for Capitol in 1954; and “All the Way” (1939), which played in the background when the college men of a previous generation did their best to bed their girlfriends.

Sinatra sang the novelty songs that Americans used to love, such as “High Hopes,” which (with changes in wording) became John F. Kennedy’s campaign theme song in 1960. As a 12-year-old boy caught up for the first time in the excitement of presidential politics, 1 well remember the new lyrics Sammy Cahn fashioned:

K- E- double-N- E- D- Y, Jack’s the nation’s favorite guy, Everyone wants to back Jack, Jack is on the right track. And he’s got high hopes, He’s got high apple-pie-in-the-sky hopes …

In 1997 a man accused of threatening to kill a former lover seemed to conduct himself according to the lyrics of Sinatra songs. Interviewed by a journalist in a diner, he sang variants on “My Way” to summarize his situation. On his former lover’s answering machine he sang “This Love of Mine” in an attempt to reconcile. (Did he know Sinatra had composed the lyrics of “This Love of Mine"? Probably not.) On the other hand, when the Apollo 11 astronauts orbited the moon in July 1969, they beamed Sinatra’s “Fly Me to the Moon” back to earth.

Humphrey Bogart was the center, and Sinatra a member, of the original Rat Pack. After Bogart’s death in 1957, Sinatra— “with his natural charisma and inability to be alone” (James Wolcott, Vanity Fair )—found himself at the center of a group that included, besides Bishop, Davis, Lawford, and Martin, the actresses Angie Dickinson and Shirley MacLaine and such others as Milton Berle and Sammy Cahn. “There is no such thing as a clan or pack,” Sinatra explained. “It’s just a bunch of millionaires with common interests who get together to have a little fun.”