
Drew Barrymore, the award-winning actress, producer and talk-show host, comes from a long line of Hollywood legends. Her grandfather John Barrymore starred in Hamlet on the London stage before making movies, and his older siblings were also distinguished actors. Late in his career, Lionel Barrymore appeared in Right Cross (1950), a sports drama in which a young Marilyn Monroe had a small part.

Drew was born to John Drew Barrymore and his wife Jaid, both actors, in 1975. Her godmother was Anna Strasberg, the third wife of Actors Studio founder Lee Strasberg (and after his death, the inheritor of Marilyn’s estate.) In 1982, Steven Spielberg cast Drew in E.T.: The Extra Terrestrial, and at seven years old, she was a household name. Her family life was troubled, however, and at fifteen, she became legally emancipated from her parents.

In 1989, Mark Sennett photographed Drew in her bedroom, surrounded by posters of Marilyn, for People magazine. “Marilyn Monroe is just the world’s greatest icon and I think her status and star only grows and rises with time,” Drew has said.

She identified with Marilyn’s difficult childhood and the intense pressure of constant press scrutiny. Admiring her ‘playful’ persona, Drew said that Marilyn’s life was ‘multi-dimensional’ and not merely defined by sadness.

In 1993, Drew posed for photographers Matthew Rolston (Seventeen) and Ellen Von Unwerth (Vogue), evoking vintage Hollywood glamour with nods to Marilyn’s bombshell style.

In Batman Forever (1995), Drew played gangster’s moll Sugar – echoing Sugar Kane in Some Like It Hot – with platinum blonde curls and risqué costumes.

But Drew’s most iconic ‘Marilyn moment’ came at the behest of none other than John F. Kennedy Jr., as People reports.
“During the Thursday, March 5 episode of The Drew Barrymore Show, the actress and host spoke with both Valerie Bertinelli and co-host Ross Mathews about her controversial 1996 cover of JFK Jr.’s magazine, in which she dressed up as Monroe … ‘I’ll never forget. I was in my home, I was in bed. I get on the phone and I’m like, “Hi” … He said, ‘I want to do something that’s gonna be controversial because I’d like you to pose as Marilyn Monroe. And, of course, I know the famous “Happy birthday, Mr. President” very well, we all do,’ she said of Monroe’s 1962 performance for JFK Jr.’s father, John F. Kennedy.
‘I said, “Oh, okay… I’d really love some direction from you on what the tone is,”‘ Barrymore added, sharing that she asked JFK Jr. if the moment was getting his ‘seal of approval,’ sly acknowledgement or if he was ‘making fun of it.’
Eventually, she asked JFK Jr. how she could “best represent this moment for you.”
‘He just said, “I want it to be straightforward. I don’t want it to be buffoonery. I don’t want it to be over congratulatory. I want it to be this sort of sensual, straightforward, confident moment,”‘ Barrymore recalled.
‘And then we went and did the shoot and I heard they were really happy with the pictures and that was great. And then I saw the magazine and I was like, “Oh my God, this is so crazy,”‘ she added of the photos by Mario Sorrenti.”

A Reddit thread notes that George’s editor-in-chief had proposed the idea to mark President Clinton’s 50th birthday. Kennedy, who founded the glossy political magazine in 1995, first asked Barbara Streisand – a friend of the Clintons – to pose as Marilyn, but she declined.
“In my brain I’m like, oh god, I don’t look anything like Marilyn Monroe,” Drew recalled. “I didn’t want to get caught up in anything scandalous, but I could just tell that everything about this cover was with a wink and a smile … I got that he wasn’t out to hurt anyone, and that’s what make me feel really inclined to do it. I was like, ‘I am so in.'”
Unsurprisingly the cover was divisive, but gave George its biggest sales to date. “It’s an enduring image,” Kennedy said. “I don’t see what possible taste questions could be involved … Just because people have clucked for decades, why does this make it strange we would use that bit of iconography? I’m intrigued that people would be indignant if I’m not.”
