Clooney stars in Sinatra role in Ocean’s Eleven remake - Dec 07, 2001 - HISTORY.com

On this day in 2001, Ocean’s Eleven, a caper film featuring an all-star ensemble cast including George Clooney, Brad Pitt, Matt Damon, Bernie Mac, Don Cheadle, Andy Garcia and Julia Roberts, opens in theaters. Ocean’s Eleven was a remake of the 1960 film of the same name, which featured so-called “Rat Pack” actors Frank Sinatra, Dean Martin, Sammy Davis, Jr., Peter Lawford and Joey Bishop, along with Angie Dickinson. Directed by Steven Soderbergh, the blockbuster 2001 remake spawned the profitable sequels Ocean’s Twelve (2004) and Ocean’s Thirteen (2007).

In 1960’s Ocean’s Eleven, Frank Sinatra starred as Danny Ocean, the ringleader of a gang of 11 accomplices who plot to rob a Las Vegas casino. At the time, the now-iconic entertainer had already won an Academy Award, in the Best Supporting Actor category, for his performance as an army private in Hawaii just before the Pearl Harbor attack in 1953’s From Here to Eternity, featuring Burt Lancaster and Deborah Kerr. Sinatra also earned a Best Actor Oscar nomination for his role as an ex-heroin addict in 1955’s The Man with the Golden Arm, with Kim Novak. Born on December 12, 1915, in Hoboken, New Jersey, Sinatra first rose to fame as a singer in the 1940s. He launched his movie career the same decade, appearing in such films as Anchors Away (1945) and Take Me Out to the Ball Game (1949), both of which co-starred Gene Kelly. Sinatra went on to star in such popular movie musicals as Guys and Dolls (1955), in which he played Nathan Detroit to Marlon Brando’s Sky Masterson, and Pal Joey (1957), with Rita Hayworth and Kim Novak. “Old Blue Eyes” also appeared in serious dramas, including The Manchurian Candidate (1962), a political thriller co-starring Laurence Harvey, Janet Leigh and Angela Lansbury. Sinatra’s final silver-screen appearance was a cameo in 1984’s Cannonball Run II, starring Burt Reynolds. The Chairman of the Board died at age 82 on May 14, 1998.

George Clooney, who took on the role of Danny Ocean in the 2001 Ocean’s Eleven remake, was born on May 6, 1961, in Lexington, Kentucky. He began his acting career on television, with supporting roles on the popular sitcoms The Facts of Life and Roseanne and the drama Sisters, as well as single episodes of such programs as The Golden Girls and Murder, She Wrote. Clooney first achieved star status with his role as Dr. Doug Ross on the prime-time medical drama ER, which debuted in 1994. By the time he left ER in 1999, Clooney had appeared in such movies as Batman & Robin (1997), Out of Sight (1998), which marked the first time Clooney worked with Soderbergh, his frequent future collaborator; and Three Kings (1999). Clooney went on to starring roles in The Perfect Storm (2000), O Brother, Where Art Thou? (2000) and Ocean’s Eleven. The handsome actor made his directorial debut with 2002’s Confessions of a Dangerous Mind, about the 1960s and ‘70s game show host Chuck Barris, who claimed he also worked for the C.I.A.

Clooney won his first Academy Award, in the Best Supporting Actor category, for his role in Syriana (2005), a complex thriller about the oil industry. That same year, he received Best Director and Best Screenplay Oscar nominations for Good Night, and Good Luck (2005), about the 1950s TV newsman Edward R. Murrow and his conflict with the anti-Communist U.S. Senator Eugene McCarthy. Clooney received his first Best Actor Oscar nomination for his performance in the title role of 2007’s legal thriller Michael Clayton.