As America’s unofficial royal family, the Kennedys have been rubbing elbows with some of the biggest names in Hollywood for decades.

In the 1960s, John F. Kennedy forged friendships with the likes of Judy Garland and Frank Sinatra, the latter of whom actively campaigned for JFK to be elected to the White House. The 35th U.S. president also infamously got close to Marilyn Monroe, who allegedly had affairs with both him and his brother Robert F. Kennedy.

JFK and RFK were not the only Kennedys who romanced celebrities though. The late commander in chief’s son John F. Kennedy Jr. was known to be quite the ladies’ man in the 1980s and 1990s. Before his marriage to Carolyn Bessette, John-John had high-profile relationships with Madonna, Cindy Crawford, Sarah Jessica Parker, Brooke Shields and, perhaps most famously, Daryl Hannah.

In more recent years, Robert F. Kennedy Jr.’s son Conor Kennedy embarked on a summer fling with Taylor Swift in 2012, and JFK’s grandnephew Patrick Schwarzenegger dated Miley Cyrus from 2014 to 2015. JFK’s great-niece Katherine Schwarzenegger, meanwhile, wed Chris Pratt in 2019.

Since marrying into the Kennedy dynasty, Pratt has become close with his in-laws. The Marvel star was even included in a massive family portrait at the famed Kennedy compound in Hyannis Port, Massachusetts, that RFK’s daughter Kerry Kennedy shared via Instagram on the 4th of July in 2019.

Pratt and Schwarzenegger added to the family in 2020 when they welcomed their daughter, Lyla, joining the actor’s son, Jack, whom he shares with his ex-wife, Anna Faris.

Scroll down to see which names in music, movies and, yes, even reality TV have ties to the Kennedys!

Gloria Swanson

The Sunset Boulevard actress’ affair with JFK’s father, Joseph P. Kennedy Sr., was an open secret in Hollywood in the late 1920s. (She was also married at the time, to French aristocrat Henry de La Falaise.) Swanson and Joe were professional partners too; he produced her 1928 movie Queen Kelly, which bombed at the box office. Their dalliance broke up Swanson’s marriage and left her in financial ruin.

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Frank Sinatra

The Rat Pack member bonded with JFK over their penchant for beautiful women and lavish parties. Sinatra became a vocal supporter of the politician ahead of the 1960 presidential election and famously re-recorded his song “High Hopes” with lyrics including, “Jack’s the nation’s favorite guy / Everyone wants to back Jack / Jack is on the right track.” Their friendship ended after JFK was sworn into office and no longer wanted to be seen with the singer, who had affiliations with the Mafia.

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Peter Lawford

The actor, who was also a member of the Rat Pack, was JFK’s brother-in-law by marriage to Patricia Kennedy Lawford. The couple, who were married from 1954 to 1966, had four children: Christopher Lawford, Sydney Maleia Lawford, Victoria Francis Lawford and Robin Elizabeth Lawford.

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Judy Garland

The Wizard of Oz star was known to call the White House or Camp David during JFK’s presidency. In turn, he would ask her to sing one of his favorite songs over the phone. “He’d request ‘Over the Rainbow,’” Garland’s third husband, Sid Luft, revealed in his 2017 memoir, Judy and I. “Judy was located somewhere in New York and obliged the president with several renditions of his favorite melodies.”

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Marilyn Monroe

After the actress sang a sultry rendition of “Happy Birthday” to JFK at Madison Square Garden in 1962, rumors swirled that the president had been cheating on his wife, Jacqueline Kennedy, with Monroe. The only known photo of the pair was taken at an afterparty later that night. The Gentlemen Prefer Blondes star was also briefly linked to RFK before her death from a barbiturate overdose later that year.

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Daryl Hannah

The Blade Runner star started seeing JFK Jr. after they both attended his aunt Lee Radziwill’s 1988 wedding to actor Herbert Ross. They broke up in 1994 following the death of his mother, Jackie, who reportedly never approved of the relationship.

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Carole Radziwill

Carole Radziwill was married to JFK Jr.’s cousin Anthony Radziwill, who served as the best man at the political scion’s 1996 wedding to Bessette. When Carole joined the cast of The Real Housewives of New York City in 2011, she insisted that she did not want to be referred to “as a Kennedy cousin.”

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Arnold Schwarzenegger

Arnold Schwarzenegger married into the family in 1986 when he wed Maria Shriver, whose maternal uncles were JFK, RFK and Ted Kennedy. The Terminator actor and the journalist welcomed four children, Katherine, Patrick, Christina Schwarzenegger and Christopher Schwarzenegger, before separating in 2011 after Arnold fathered a child with their housekeeper.

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Chris Pratt

In 2019, the Parks and Recreation alum married Katherine, the great-niece of JFK, RFK and Ted. They welcomed their daughter, Lyla, the following year.

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Cheryl Hines

The Curb Your Enthusiasm alum married RFK Jr. in 2014. He was previously married to Emily Black, whom he divorced in 1994, and Mary Richardson, who died in 2012.

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Miley Cyrus

The “Wrecking Ball” singer dated Maria and Arnold’s son Patrick on and off from 2014 to 2015. Miley’s brother Braison Cyrus was briefly linked to Patrick’s sister Christina around the same time.

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Taylor Swift

The hitmaker, who wrote her song “Starlight” about RFK and Ethel Kennedy after reading Laurence Leamer’s book The Kennedy Women, was in a relationship with Conor for a few months in 2012. That summer, she bought a home in Cape Cod, Massachusetts, near the Kennedy compound, only to sell it a few months later.

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