| Lists |

Top Ten Things That Make Frank Sinatra Cool

Keep New Times Free
I Support
  • Local
  • Community
  • Journalism
  • logo

Support the independent voice of Phoenix and help keep the future of New Times free.

When it comes to crooners, they don't get any cooler than Frank Sinatra. Over the course of his 60-year career, "Old Blue Eyes" won a dozen Grammy Awards, three Academy Awards, and recorded 297 singles, including hits like "Theme from New York, New York," "My Way," and "Strangers in the Night."

So it's only fitting that there's a Tribute to Sinatra at Sky Restaurant in Peoria on Saturday, July 9. Valley resident and Sinatra lookalike Guy Pennacchio, who appeared on Dick Clark's Your Big Break on UPN in 2000, will do his best renditions of Sinatra Songs.

But it wasn't just Frank Sinatra's ability to sing, win awards, and inspire tributes that made him cool. Here are ten more things that made him a super suave star.

10. The FBI was obsessed with him. The FBI watched Sinatra for almost 50 years, beginning in the 1940s, and amassed some 2,403 pages of records on him. In response to requests under the Freedom of Information Act, the FBI dossier on Sinatra was released in 1998. The declassified files revealed, among other things, threats of death and extortion against Sinatra, investigations of Sinatra's alleged mafia ties and Communist associations, and his offer to be an informer for the organization (they declined).

9. He was a founding member of the 1960s Rat Pack

. The first supergroup of multi-talented stars, the Rat Pack -- Sinatra, Sammy Davis Jr., Dean Martin, Peter Lawford, and Joey Bishop -- never referred to themselves by that name, instead calling themselves the Summit or the Clan. But the press loved the moniker, and the Rat Pack stuck. Along with Davis Jr. and Martin, Sinatra was considered one of the leaders of the group.

8. He shared a famous woman with Woody Allen. From 1966 to 1968, Sinatra was married to actress Mia Farrow, who was thirty years his junior. In 1980, she began an ill-fated 12-year relationship with Allen, who would leave her for one of their adopted children.

7. He learned music by ear. Sinatra never learned to read music, and did well enough hitting pitch without learning how to translate notes on paper. He was obviously way too cool for that.

6. He founded Reprise Records. The Sinatra nickname, "Chairman of the Board," was born in 1960, the year he founded Reprise. The label, which Sinatra sold to Warner Bros. Records in 1963, went on to boast a roster that included Joni Mitchell, Neil Young, Captain Beefheart, Frank Zappa, T. Rex, The Beach Boys, Fleetwood Mac, Green Day, Mastodon, My Chemical Romance, and Disturbed.

5. He made the Empire State Building glow blue. This was done to mark Sinatra's 80th birthday in 1995.

4. He was friends with President John F. Kennedy. Sinatra and the Rat Pack played a big role in Kennedy's 1960 campaign, for which the theme song was "High Hopes," sung by Sinatra, who'd recorded a special track with lyrics about Kennedy worked in. In January of 1961, Sinatra and Peter Lawford organized Kennedy's Inaugural Gala. Legend has it the friendship soured when Sinatra prepared a room at his house for Kennedy in anticipation of the president's visit to Palm Springs in 1962, but JFK opted to stay with Bing Crosby instead.

3. He performed for Anwar Sadat in front of the Egyptian pyramids. Talk about a collection of legends: The only remaining of the seven ancient wonders of the world (the Great Pyramid of Giza), a Nobel Peace Prize winner (then-president of Egypt, Anwar Sadat), and Frank Sinatra. It happened in 1979, two years before Sadat was assassinated.

2. He was a civil rights activist. In 1961, Sinatra played a benefit show for Martin Luther King, Jr. at Carnegie Hall (one of many benefits Sinatra did for King), and led a massive artist boycott on hotels and casinos in Nevada that refused to admit black patrons and performers.   

1. He was Frank fucking Sinatra.

Why Indie Band Oregon Trail Is The Hardest Game Ever The 30 Most Disturbing Songs of All Time Here's How Not to Approach a Journalist on Facebook Seven Terrible First Pitches by Otherwise Coordinated Pop Stars

Like Up on the Sun on Facebook or follow us on Twitter for the latest local music news and conversation.

Keep Phoenix New Times Free... Since we started Phoenix New Times, it has been defined as the free, independent voice of Phoenix, and we would like to keep it that way. Offering our readers free access to incisive coverage of local news, food and culture. Producing stories on everything from political scandals to the hottest new bands, with gutsy reporting, stylish writing, and staffers who've won everything from the Society of Professional Journalists' Sigma Delta Chi feature-writing award to the Casey Medal for Meritorious Journalism. But with local journalism's existence under siege and advertising revenue setbacks having a larger impact, it is important now more than ever for us to rally support behind funding our local journalism. You can help by participating in our "I Support" membership program, allowing us to keep covering Phoenix with no paywalls.

We use cookies to collect and analyze information on site performance and usage, and to enhance and customize content and advertisements. By clicking 'X' or continuing to use the site, you agree to allow cookies to be placed. To find out more, visit our cookies policy and our privacy policy.


Join the New Times community and help support independent local journalism in Phoenix.


Join the New Times community and help support independent local journalism in Phoenix.