Famous Friendships: Grace Kelly & Frank Sinatra

Hollywood isn’t known as the best place to make real, long-lasting friendships. Celebs can be as on-again-off-again in their friendships as their romances, and keeping up with who’s gone from ride-or-die to frenemies is a full-time job. (Case in point: whatever happened to Taylor Swift’s squad?)

But when A-lister Grace Kelly left the bright lights of Hollywood for the glittering shores of Monaco, she put in the work to stay in touch with her co-star friends. One of the friends who made the cut was Ol’ Blue Eyes himself, Frank Sinatra. Here’s how their friendship survived Tinseltown and international travel.

Stars Align

The pair first crossed paths on the 1952 set of Mogambo, an adventure-romance set in Kenya. Sinatra’s wife at the time, Ava Gardner, starred opposite Clark Gable and 23-year-old Grace Kelly in what was only Grace Kelly’s third feature film.

“Mogambo had three things that interested me: John Ford, Clark Gable, and a trip to Africa.”

The Nairobi heat caused problems for the production, and to add to the drama, Sinatra and Gardner’s marriage wasn’t going well. Those on set recall hearing the couple fighting, and they split shortly after Mogambo premiered. Grace Kelly didn’t let the stress impact her first impressions, becoming friends with both Gardner and Sinatra.

On the Rise

While Sinatra recovered from a career slump, Grace Kelly’s Mogambo performance drew attention, and she landed a contract with MGM Studios. she went on to star in 1954’s The Country Girl, and nabbed both a Golden Globe and an Oscar for Best Actress.

While promoting the movie in Cannes, she was introduced to future husband Prince Rainier III of Monaco by fellow movie star Olivia de Havilland. The romance would mean a change in both Grace Kelly’s career and her address, and she starred in Her final Hollywood film, High Society, in 1956. The on-screen love triangle included her The Country Girl co-star Bing Crosby as her jazz musician ex-husband and her off-screen friend, Sinatra, as her potential new romance. Despite their age gap—Sinatra was 14 years older than Grace Kelly—their off-screen friendship continued to thrive, and High Society was considered one of the biggest films of the year. (You could even say it was sensational.)

That spring saw the wedding of the century. Like something out of a movie, thousands of people lined the streets of Monaco, and 600 guests were invited to witness the marriage of Prince Rainier III and Princess Grace. The event was not short on celebs, including Grace Kelly’s Mogambo co-star Ava Gardner. Sinatra, who was in the middle of a huge career comeback, thoughtfully stayed home to avoid stealing the royal couple’s thunder on their wedding day.

Charitable Reunions

The two friends were reunited in 1958 for a United Nations Refugee Fund benefit concert in Monte Carlo hosted by Princess Grace. Sinatra had returned to Europe to promote his latest film, Kings Go Forth, and a young Quincy Jones, who was living in Paris at the time, was invited to direct his orchestra at the Sporting Club in Monaco. Near the end of the star-studded night, which included famous writers and actors in the audience as well as on stage, Sinatra said that he and the band would play “You Make Me Feel So Young” because Princess Grace had requested it. Despite having never rehearsed that number with the orchestra, Sinatra jokingly told the band to relax—and the performance was perfect.

“Just read it. Don’t be nervous, fellas, everything will be cool.”

Sinatra and Princess Grace remained permanent fixtures in each other's lives. He often visited the royal family in Monaco, and stayed for movie nights in the palace screening room. “I remember different parties and luncheons in the summer, where we'd have Frank Sinatra, Kirk Douglas, Gregory Peck come by,” Princess Grace’s son Prince Albert told 60 Minutes. And while Sinatra was absent at Princess Grace’s wedding, he attended the wedding of her oldest daughter, Princess Caroline, in 1978.

After Princess Grace’s death, Prince Rainier III asked His wife’s greatest friends, including Sinatra, to help set up the Princess Grace Foundation-USA in her memory. At Princess Grace’s memorial, Sinatra paid tribute to his “angel” friend. “She was a beautiful human being,” Sinatra said. “She was the most incredible human being I've ever known. Everything she touched came alive.”

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Grace Kelly made a loyal friend—and an unforgettable princess. Discover what she taught the world about being a royal.

Credits: Associated Press/Indiana Gazette, Princess Grace Foundation, Lubbock Evening Journal