Robert De Niro, Bill Murray And Al Pacino Pair with (Much) Younger Women. Rather, Rinse, Repeat

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The new Anna Nicole Smith documentary came out at an oddly perfect time given recent headlines.

“Anna Nicole Smith: You Don’t Know Me” recalls the Playboy model’s curious romance with an 80-something Billionaire J. Howard Marshall. She was 26 and he was 89 and unable to walk without a wheelchair at the time of their marriage.

“I’m sick of being accused of gold–digging. It just so happens I get turned on by liver spots,” she said about their unusual bond at the time.

Their gargantuan age difference rocked the press back in the 1990s, with naysayers then (and now) contending it was all about cash, not romance.

Now, we’re seeing three more cartoonish examples of older men with much younger women from the world of, where else, Hollywood. Each of the men in question likely have considerable wallets at this point in their illustrious careers.

We recently learned that Oscar-winner Robert De Niro, 79, took enough time away from bashing Donald Trump to become a father for the seventh time with his 45-year-old girlfriend Tiffany Chen. The pair met on a movie set and De Niro quietly shared the news of their bundle of joy with the media while promoting his new comedy “About My Father” with Sebastian Maniscalco.

NEW YORK, NEW YORK – JUNE 17: Robert De Niro (L) and Al Pacino attend “Heat” Premiere during 2022 Tribeca Festival at United Palace Theater on June 17, 2022 in New York City. (Photo by Dominik Bindl/WireImage)

Robert De Niro Is Not Alone In His

Not to be outdone, fellow “Godfather II” alum Al Pacino, 83, announced he’s becoming a daddy again with 29-year-old squeeze Noor Alfallah. It’s the “Scent of a Woman” star’s fourth child, and he fought back rumors that he was less than thrilled upon hearing the news.

Now, because everything seems to come in threes, we’re learning of yet another late May, early December Hollywood romance.

Press reports say “Ghostbusters” legend Bill Murray, 72, is dating 43-year-old singer/chef Kelis. Murray has been semi-canceled in recent months for his outlandish behavior on various movie sets over the years, but he did appear in the recent MCU film “Ant Man and the Wasp: Quantumania.”

USA Today leaned into the Pacino and De Niro announcements, declaring their stories were part of a larger “privilege” conversation we need to be having.

Women face a constantly ticking biological clock that impacts many facets of their lives, and men, simply, do not. Pacino and DeNiro’s recent headline-making announcements might sting for some, making this inequity harder to ignore, experts say.

USA Today

The left-wing guardian called the Pacino-De Niro superstars as having the “daddy of all rivalries.”

Hollywood romances of this nature routinely draw attention. Many have forgotten the dubious news cycles concerning Jerry Seinfeld’s romance with a much younger woman. He was 38 at the time, and Shoshanna Lonstein hadn’t yet turned 18 when the rumor mill kicked in about their connection.

“She’s a person, not an age,” the comic legend said in his defense at the time.

To their credit, they dated for five years before going their separate ways, but Seinfeld became the butt of many jokes as a result. Shock jock Howard Stern infamously roasted the comedian with singer Janis Ian contributing to a satirical cover of her classic song, “At Seventeen.”

“Can’t he find girls his age to date/She’s 17 and she’s jail bait,” Stern crooned with Ian. “She barely shed her training bra/She kisses lips for candy bars.”

Three of our greatest living actors are doubling down on an old dating saw – you’re never too old to date a younger woman. Add the celebrity angle into the mix and the only surprise is that the age gap isn’t even bigger.

Written by Christian Toto

Christian Toto is an award-winning film critic, journalist and founder of, the Right Take on Entertainment. He’s the author of “Virtue Bombs: How Hollywood Got Woke and Lost Its Soul” and a lifelong Yankees fan. Toto lives in Denver, Colorado with his wife, two sons and too many chickens.

Follow Christian on Twitter at

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