Home > News & Advice > Frank Sinatra Did It His Way

Frank Sinatra Did It His Way

by Legacy Staff

Also known as “Ol’ Blue Eyes” and “The Chairman of the Board,” Frank Sinatra became an icon of cool in postwar America.

On May 14, 1998, “The Voice” went silent for the last time when Frank Sinatra died at 82.

Also known as “Ol’ Blue Eyes” and “The Chairman of the Board,” Sinatra became an icon of cool in postwar America. He sold millions of records during a recording career spanning seven decades, and he continues to sell records today. He also sang, danced and acted his way through a string of classic film musicals like “Pal Joey,” “Guys and Dolls” and “On the Town.” Sinatra became legendary for his wild bachelor lifestyle, along with his friends Dean Martin and Sammy Davis Jr. and the so-called Rat Pack. He even made heist movie “Ocean’s Eleven” with the rest of the Pack.


While success as a recording artist and comedic actor seemingly came easily to Sinatra, he continued to push himself as an artist in the 1950s and ’60s, starring in the dramas “The Manchurian Candidate” and “From Here to Eternity,” winning the best supporting actor Oscar for the latter.

His personal life was as colorful as his life onscreen, with stories circulating for decades of his involvement with organized crime. While those ties were never confirmed, despite decades of FBI surveillance compiled into a file over 2,400 pages long, the relationships we do know about were no less interesting. He was married to four different women, including Ava Gardner and Mia Farrow, and romantically linked to Judy Garland, Lauren Bacall, Marilyn Monroe and others. He worked on behalf of the Roosevelt administration early in his career, and he campaigned for both John F. Kennedy and Ronald Reagan in their successful bids for the White House. Sinatra remained a vital, fascinating part of American culture through his later years, performing into the 1990s and inspiring two different parodies on Saturday Night Live.

After Sinatra died of a heart attack in 1998, he was buried beneath the epitaph, borrowed from one of his most famous songs, “The Best Is Yet to Come.”

Originally published May 2014

More Stories